Substituted tryptamine

{{Short description|Class of indoles}} thumb|right|200px|class=skin-invert-image|The structure of substituted tryptamines. Tryptamine itself is obtained when R4=R5=RN₁=RN₂=Rα = H. thumb|right|175px|class=skin-invert-image|The structure of substituted tryptamines with all positions labeled.

'''Substituted tryptamines''', or simply '''tryptamines''', also known as '''serotonin analogues''' (i.e., '''5-hydroxytryptamine analogues'''), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring system, joined to an amino (NH₂) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.

Well-known tryptamines include serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine alkaloids are found in fungi, plants and animals; and sometimes used by humans for the neurological or psychotropic effects of the substance. Prominent examples of tryptamine alkaloids include psilocybin (from "psilocybin mushrooms") and DMT. In South America, dimethyltryptamine is obtained from numerous plant sources, like chacruna, and it is often used in ayahuasca brews. Many synthetic tryptamines have also been made, including the migraine drug sumatriptan, and psychedelic drugs. A 2022 study has found the variety of tryptamines present in wild mushrooms may affect the therapeutic impact.<ref>{{Cite web |last1=Chemistry |first1=University of |last2=Prague |first2=Technology |title=Concentrations of psychoactive compounds in mushrooms found to be extremely variable |url=https://phys.org/news/2022-12-psychoactive-compounds-mushrooms-extremely-variable.html |access-date=2022-12-26 |website=phys.org |language=en}}</ref>

The tryptamine structure, in particular its indole ring, may be part of the structure of some more complex compounds, for example cyclized tryptamines like LSD, ibogaine, harmaline, mitragynine and yohimbine. A thorough investigation of dozens of tryptamine compounds was published by Alexander Shulgin and Ann Shulgin in 1997 under the title ''TiHKAL'' (''Tryptamines I Have Known and Loved'').<ref name="TiHKAL">{{CiteTiHKAL}}</ref>

==Use and effects== The doses, potencies, durations, and effects of psychedelic tryptamines have been reviewed by Alexander Shulgin and other authors.<ref name="JacobShulgin1994">{{cite journal | vauthors = Jacob P, Shulgin AT | title = Structure-activity relationships of the classic hallucinogens and their analogs | journal = NIDA Res Monogr | volume = 146 | issue = | pages = 74–91 | date = 1994 | pmid = 8742795 | doi = | url = https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79 | archive-url = https://web.archive.org/web/20230805004551/https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79 | archive-date = August 5, 2023 }}</ref><ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | chapter=Basic Pharmacology and Effects | pages=67–137 | veditors = Laing RR | title=Hallucinogens: A Forensic Drug Handbook | publisher=Elsevier Science | series=Forensic Drug Handbook Series | year=2003 | isbn=978-0-12-433951-4 | url=https://books.google.com/books?id=l1DrqgobbcwC | chapter-url=https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6}}</ref><ref name="Shulgin1982">{{cite book |vauthors=Shulgin AT | chapter=Chemistry of Psychotomimetics | pages = 3–29 | veditors = Hoffmeister F, Stille G | title=Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs | series=Handbook of Experimental Pharmacology | publisher=Springer Berlin Heidelberg |location=Berlin |date=1982 | volume=55 / 3 |isbn=978-3-642-67772-4 | oclc = 8130916 | doi=10.1007/978-3-642-67770-0_1 | url = https://books.google.com/books?id=mrT8CAAAQBAJ | chapter-url = https://bitnest.netfirms.com/external/10.1007/978-3-642-67770-0_1}}</ref><ref name="Shulgin1980">{{cite book | author = Alexander T. Shulgin | chapter = Hallucinogens | pages = 1109–1137 | chapter-url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5 | veditors = Burger A, Wolf ME | title = Burger's Medicinal Chemistry | edition = 4 | volume = 3 | date = 1980 | publisher = Wiley | location = New York | isbn = 978-0-471-01572-7 | oclc = 219960627 | url = https://books.google.com/books?id=2b3wAAAAMAAJ}}</ref><ref name="TiHKAL" /><ref name="LuethiLiechti2018">{{cite journal | vauthors = Luethi D, Liechti ME | title = Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics | journal = Int J Neuropsychopharmacol | volume = 21 | issue = 10 | pages = 926–931 | date = October 2018 | pmid = 29850881 | pmc = 6165951 | doi = 10.1093/ijnp/pyy047 }}</ref><ref name="HalberstadtChathaKlein2020">{{cite journal |last1=Halberstadt |first1=Adam L. |last2=Chatha |first2=Muhammad |last3=Klein |first3=Adam K. |last4=Wallach |first4=Jason |last5=Brandt |first5=Simon D. |date=May 2020 |title=Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species |url=http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf |journal=Neuropharmacology |volume=167 |doi=10.1016/j.neuropharm.2019.107933 |pmc=9191653 |pmid=31917152 |quote=Table 4 Human potency data for selected hallucinogens. [...] |article-number=107933 |archive-url=https://web.archive.org/web/20250326111621/http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf |archive-date=26 March 2025 }}</ref><ref name="BallentineFriedmanBzdok2022">{{cite journal |last1=Ballentine |first1=Galen |last2=Friedman |first2=Samuel Freesun |last3=Bzdok |first3=Danilo |date=March 2022 |title=Trips and neurotransmitters: Discovering principled patterns across 6850 hallucinogenic experiences |journal=Sci Adv |volume=8 |issue=11 |bibcode=2022SciA....8L6989B |doi=10.1126/sciadv.abl6989 |pmc=8926331 |pmid=35294242 |article-number=eabl6989}}</ref><ref name="MallaroniMasonVinckenbosch2022">{{cite journal | vauthors = Mallaroni P, Mason NL, Vinckenbosch FR, Ramaekers JG | title = The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides | journal = Psychopharmacology (Berl) | volume = 239 | issue = 6 | pages = 1783–1796 | date = June 2022 | pmid = 35487983 | pmc = 9166850 | doi = 10.1007/s00213-022-06142-4 | url = }}</ref><ref name="McKennaTowers1984">{{cite journal | vauthors = McKenna DJ, Towers GH | title = Biochemistry and pharmacology of tryptamines and beta-carbolines. A minireview | journal = J Psychoactive Drugs | volume = 16 | issue = 4 | pages = 347–358 | date = 1984 | pmid = 6394730 | doi = 10.1080/02791072.1984.10472305 | url = https://bitnest.netfirms.com/external/10.1080/02791072.1984.10472305| url-access = subscription }}</ref>

===Ring-unsubstituted tryptamines=== {{Sticky}} {| class="wikitable sortable sticky-header" |+ {{Nowrap|Oral doses and durations of ring-unsubstituted tryptamines}} |- ! Compound !! Chemical name !! Dose !! Duration |- | Tryptamine (T) || Tryptamine || >100&nbsp;mg^a || – |- | NMT || ''N''-Methyltryptamine || Unknown^b || – |- | NET || ''N''-Ethyltryptamine || Unknown || Unknown |- | NPT || ''N''-Propyltryptamine || Unknown || Unknown |- | NiPT || ''N''-Isopropyltryptamine || Unknown || Unknown |- | NsBT || ''N''-''sec''-Butyltryptamine || 25–75&nbsp;mg || "Short" |- | NtBT || ''N''-''tert''-Butyltryptamine || 5–20&nbsp;mg || Unknown |- | NAT || ''N''-Amyltryptamine || >100&nbsp;mg || – |- | NHT || ''N''-Hexyltryptamine || >100&nbsp;mg || – |- | DMT || ''N'',''N''-Dimethyltryptamine || >350–1,000&nbsp;mg^c || – |- | DET || ''N'',''N''-Diethyltryptamine || 50–150&nbsp;mg || 2–4 hours |- | DPT || ''N'',''N''-Dipropyltryptamine || 100–250&nbsp;mg || 2–4 hours |- | DiPT || ''N'',''N''-Diisopropyltryptamine || 25–100&nbsp;mg (15–150&nbsp;mg+) || 4–8 hours |- | DALT || ''N'',''N''-Diallyltryptamine || 60–80&nbsp;mg || <3 hours |- | DBT || ''N'',''N''-Dibutyltryptamine || ≥100&nbsp;mg || Unknown |- | DAT || ''N'',''N''-Diamyltryptamine || Unknown || Unknown |- | DHT || ''N'',''N''-Dihexyltryptamine || >100&nbsp;mg || – |- | MET || ''N''-Methyl-''N''-ethyltryptamine || 80–100&nbsp;mg || Unknown |- | MPT || ''N''-Methyl-''N''-propyltryptamine || >50&nbsp;mg || Unknown |- | MiPT || ''N''-Methyl-''N''-isopropyltryptamine || 10–25&nbsp;mg || 3–4 hours |- | MALT || ''N''-Methyl-''N''-allyltryptamine || 25–50&nbsp;mg || Unknown |- | MBT || ''N''-Methyl-''N''-butyltryptamine || 250–400&nbsp;mg || 4–6 hours |- | MsBT || ''N''-Methyl-''N''-''sec''-butyltryptamine || 250–400&nbsp;mg || Unknown |- | EPT || ''N''-Ethyl-''N''-propyltryptamine || Unknown || Unknown |- | EiPT || ''N''-Ethyl-''N''-isopropyltryptamine || 24–40&nbsp;mg || 4–6 hours |- | PiPT || ''N''-Propyl-''N''-isopropyltryptamine || Unknown || Unknown |- | Pyr-T || ''N'',''N''-Tetramethylenetryptamine || Unknown<!--or ~100 mg--> || Unknown |- | Pip-T || ''N'',''N''-Pentamethylenetryptamine || Unknown || Unknown |- | Mor-T || 3-(2-Morpholinoethyl)indole || Unknown^d || Unknown |- class="sortbottom" | colspan="5" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Footnotes:''' ^a = Tryptamine is not orally active, but is active intravenously at a dose of 250{{nbsp}}mg with a very short duration. ^b = NMT is not orally active, but is said to be active smoked at a dose of 50 to 120{{nbsp}}mg with a duration of seconds to minutes. Also reportedly orally active with an {{Abbrlink|MAOI|monoamine oxidase inhibitor}}. ^c = DMT is active parenterally at doses of 50 to 100{{nbsp}}mg (2–100{{nbsp}}mg) smoked, intramuscularly, or subcutaneously and at doses of 4 to 30{{nbsp}}mg intravenously (bolus), with a duration of <1 hour or 5–20{{nbsp}}minutes. For continuous intravenous infusion, the dose is 0.6 to 2.4{{nbsp}}mg/minute. Also orally active with an {{Abbr|MAOI|monoamine oxidase inhibitor}} (as in ayahuasca or pharmahuasca), with a typical dose of 50{{nbsp}}mg (range 20–120{{nbsp}}mg) and a duration of 4 to 6{{nbsp}}hours. ^d = Mor-T was inactive at a dose of 30{{nbsp}}mg by intramuscular injection. '''Refs:''' <ref name="JacobShulgin1994" /><ref name="Shulgin2003" /><ref name="TiHKAL" /><ref name="LuethiLiechti2018" /><ref name="HalberstadtChathaKlein2020" /><ref name="BallentineFriedmanBzdok2022" /><ref name="McKennaTowers1984" /> ''Individual:'' <ref name="Nen2011">{{cite conference | author = Nen | title = Entheogenic effects of NMT from Acacia | conference = Entheogenesis Australis (EGA) Conference, Victoria, Australia, 2–5 December 2011 | date = 4 December 2011 | url = https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=300323&%23post300323 | conference-url = https://web.archive.org/web/20120226052047/http://www.entheo.net/files/webfiles/ega11_program_v7.pdf | access-date = 15 April 2025 | archive-date = 5 April 2025 | archive-url = https://archive.today/20250405014754/https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=300323&%23post300323 | url-status = bot: unknown }}</ref><ref name="Nen2013">{{cite conference | author = Nen | title = NMT: A Spatial Hallucinogen With Therapeutic Applications | conference = Breaking Convention: The Second Multidisciplinary Conference on Psychedelic Consciousness, University of Greenwich, London, 12–14 July 2013 | date = 13 July 2013 | url = https://www.youtube.com/watch?v=98WXxyb2u4A | conference-url = https://breakingconvention.co.uk/archive#conferenceArchive}}</ref><ref name="LiechtiHolze2022">{{cite book | vauthors = Liechti ME, Holze F | title = Disruptive Psychopharmacology | chapter = Dosing Psychedelics and MDMA | series = Curr Top Behav Neurosci | volume = 56 | pages = 3–21 | date = 2022 | pmid = 34734392 | doi = 10.1007/7854_2021_270 | isbn = 978-3-031-12183-8 | chapter-url = }}</ref><ref name="HolzeSinghLiechti2024">{{cite journal | vauthors = Holze F, Singh N, Liechti ME, D'Souza DC | title = Serotonergic Psychedelics: A Comparative Review of Efficacy, Safety, Pharmacokinetics, and Binding Profile | journal = Biol Psychiatry Cogn Neurosci Neuroimaging | volume = 9 | issue = 5 | pages = 472–489 | date = May 2024 | pmid = 38301886 | doi = 10.1016/j.bpsc.2024.01.007 | url = | doi-access = free }}</ref><ref name="DosSantosHallak2024">{{cite journal | vauthors = Dos Santos RG, Hallak JE | title = Ayahuasca: pharmacology, safety, and therapeutic effects | journal = CNS Spectr | volume = 30 | issue = 1 | article-number = e2 | date = November 2024 | pmid = 39564645 | doi = 10.1017/S109285292400213X | url = | quote = DMT has been found to be inactive orally in doses as high as 1 g, but it has been found to be psychoactive after intramuscular administration (0.25-2.00 mg/kg), when inhaled as vaporized free-base (0.2-0.7 mg/kg), and after intravenous administration (0.2-0.4 mg/kg).8–10 [...] In the case of ayahuasca, since pure DMT is not orally psychoactive (doses up to 1 g are inactive in humans51) due to peripheral (gastrointestinal and hepatic) metabolization by MAO-A, [...]| doi-access = free }}</ref><ref name="Barker2022">{{cite journal | vauthors = Barker SA | title = Administration of N,N-dimethyltryptamine (DMT) in psychedelic therapeutics and research and the study of endogenous DMT | journal = Psychopharmacology (Berl) | volume = 239 | issue = 6 | pages = 1749–1763 | date = June 2022 | pmid = 35064294 | pmc = 8782705 | doi = 10.1007/s00213-022-06065-0 | url = | quote = Doses for vaporized or inhaled free-base DMT are typically 40–50 mg, although larger doses have been reported (100 mg; Shulgin and Shulgin 1997). Pallavicini et al. (2021) have reported that vaporization of approximately 40 mg of DMT, administered in a natural setting, produced potential electroencephalographic markers of mystical-type experiences in 35 volunteers. The onset of effects for inhaled DMT is rapid, similar to that of IV administration, but lasts less than 30 min (Riba et al. 2015; Davis et al. 2020). [...] For administration of pharmahuasca, 50 mg DMT:100 mg harmaline is usually the recommended dosage. However, combinations of 50 mg harmaline:50 mg harmine and 50 mg DMT have been tested with success. The harmalas and DMT are typically put into separate gelatin capsules, with the harmaline/harmine being taken first and the DMT being taken 15 to 20 min later. The use of moclobemide, a reversible inhibitor of MAO-A, has also been reported in DMT "pharmahuasca" studies (Kaasik et al. 2020; Ruffell et al. 2020).}}</ref><ref name="EggerAicherCumming2024">{{cite journal | vauthors = Egger K, Aicher HD, Cumming P, Scheidegger M | title = Neurobiological research on N,N-dimethyltryptamine (DMT) and its potentiation by monoamine oxidase (MAO) inhibition: from ayahuasca to synthetic combinations of DMT and MAO inhibitors | journal = Cell Mol Life Sci | volume = 81 | issue = 1 | article-number = 395 | date = September 2024 | pmid = 39254764 | pmc = 11387584 | doi = 10.1007/s00018-024-05353-6 | url = | quote = Recent studies tested i.v. DMT with different administration regimens. Such protocols entailed 0–19.2 mg bolus 0.5–0.8 mg/min constant infusion of DMT freebase (as hemifumarate) for up to 90 min (Basel) [7], 11.2 mg bolus 1.2 mg/min infusion of DMT freebase (as fumarate) for up to 30 min (London) [8], and constant infusion totaling 13.4 mg DMT freebase (as fumarate) over 10 min (London) [110]). [...] The various β-carbolines in B. caapi, especially harmine and harmaline, enable the attainment of sufficient plasma DMT concentrations to evoke psychedelic effects lasting 4–6 h [5, 61].}}</ref><ref name="Ott1999">{{cite journal | vauthors = Ott J | title = Pharmahuasca: human pharmacology of oral DMT plus harmine | journal = J Psychoactive Drugs | volume = 31 | issue = 2 | pages = 171–177 | date = 1999 | pmid = 10438001 | doi = 10.1080/02791072.1999.10471741 | url = | quote = Since the β-carbolines per se could not explain the legendary psychoptic (visionary) activity of the jungle ambrosia, this had to be due to its DMT content, which amounted to an average of 29 mg/dose in the 16 potions analyzed (range: 25-36 mg/dose). [...] TABLE 1 Human Pharmacology of Psychoptic Tryptamines [...]}}</ref><ref name="BrimblecombePinder1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | pages = 98–144 | title = Hallucinogenic Agents | date = 1975 | publisher = Wright-Scientechnica | location = Bristol | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1 | quote = Other N,N-dialkyltryptamines produce similar effects to DMT in man, though their persistence is somewhat greater, with hallucinations lasting for up to 3 hours (Szara and Hearst, 1962). These include the N,N-diethyl (DET, 4.8), N,N-dipropyl (4.9), and N,N-diallyl (4.10) compounds, none of which are found in nature.}}</ref><ref name="SzaraHearst1962" /><ref name="Nichols_1984">{{cite book | vauthors = Nichols DE, Glennon RA | veditors = Jacobs BL | chapter = Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens | title = Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives | location = New York | pages = 95–142 | date = 1984 | publisher = Raven Press | isbn = 978-0-89004-990-7 | oclc = 10324237 | url = https://books.google.com/books?id=EdpsAAAAMAAJ&pg=PA95 | chapter-url = https://bitnest.netfirms.com/external/Books/HallucinogensNBCP95 | quote = Szara and co-workers (221,223,225) noted psychotomimetic activity for N,N-diethyltryptamine (DET; 38) at a dose of 1 mg/kg. [...] N,N-Dipropyltryptamine (DPT; 39) is also hallucinogenic in man at 1 mg/kg (222). [...] Branching of the propyl groups results in N,N-diisopropyltryptamine (DIPT; 40), which is orally active at 20 to 50 mg (202). N,N-Dibutyltryptamine (DBT; 41) and N,N-dihexyltryptamine (DHT; 42) have been examined only briefly. At 1 mg/kg, DBT produced only slight perceptual, emotional, and thinking disturbances in man, while DHT at the same dose was completely inactive (222). }}</ref><ref name="Szára1961">{{cite journal | last=Szára | first=S. | title=104 Correlation between Metabolism and Behavioural Action of Psychotropic Tryptamine Derivatives | journal=Biochemical Pharmacology | volume=8 | issue=1 | date=1961 | doi=10.1016/0006-2952(61)90278-7 | page=32 | quote=N,N-dimethyltryptamine and its N,N-diethyl and N,N-dipropyl homologues produce autonomic symptoms, perceptual, emotional, and thinking disturbances in man (in doses of 1 mg/kg) similar to LSD25 or mescalin but for a much shorter period of time. The corresponding dibutyl derivative causes only very slight symptoms while the dihexyl compound is completely inactive in the same dose.}}</ref> |}

===4-Hydroxytryptamines=== {{Sticky}} {| class="wikitable sortable sticky-header" |+ {{Nowrap|Oral doses and durations of 4-hydroxytryptamines}} |- ! Compound !! Chemical name !! Dose !! Duration |- | 4-HT (4-HO-T) || 4-Hydroxytryptamine || Unknown || Unknown |- | Norbaeocystin (4-PO-T) || 4-Phosphoryloxytryptamine || Unknown || Unknown |- | Norpsilocin (4-HO-NMT) || 4-Hydroxy-''N''-methyltryptamine || Unknown || Unknown |- | Baeocystin (4-PO-NMT) || 4-Phosphoryloxy-''N''-methyltryptamine || 4–10&nbsp;mg^a || Unknown |- | Psilocin (4-HO-DMT) || 4-Hydroxy-''N'',''N''-dimethyltryptamine || 10–20&nbsp;mg (5–40&nbsp;mg+) || 3–6 hours |- | Psilocybin (4-PO-DMT) || 4-Phosphoryloxy-''N'',''N''-dimethyltryptamine || 10–20&nbsp;mg (5–40&nbsp;mg+) || 3–6 hours |- | 4-AcO-DMT (psilacetin) || 4-Acetoxy-''N'',''N''-dimethyltryptamine || 10–30&nbsp;mg || 3–8 hours |- | 4-PrO-DMT || 4-Propionyloxy-''N'',''N''-dimethyltryptamine || Unknown || Unknown |- | 4-HO-DET (ethocin) || 4-Hydroxy-''N'',''N''-diethyltryptamine || 10–25&nbsp;mg || 4–6 hours |- | Ethocybin (4-PO-DET) || 4-Phosphoryloxy-''N'',''N''-diethyltryptamine || 15–30&nbsp;mg || 4–6 hours |- | 4-HO-DPT (deprocin) || 4-Hydroxy-''N'',''N''-dipropyltryptamine || >20&nbsp;mg || 5–8 hours |- | 4-HO-DiPT (iprocin) || 4-Hydroxy-''N'',''N''-diisopropyltryptamine || 12–20&nbsp;mg (3–30&nbsp;mg+) || 2–3 hours |- | 4-AcO-DiPT (ipracetin) || 4-Acetoxy-''N'',''N''-diisopropyltryptamine || 6–10&nbsp;mg || Unknown |- | Luvesilocin (4-GO-DiPT) || 4-Glutaryloxy-''N'',''N''-diisopropyltryptamine || Unknown^b || Unknown^b |- | 4-HO-DALT (daltocin) || 4-Hydroxy-''N'',''N''-diallyltryptamine || Unknown || Unknown |- | 4-HO-DBT || 4-Hydroxy-''N'',''N''-dibutyltryptamine || >20&nbsp;mg || Unknown |- | 4-HO-DiBT || 4-Hydroxy-''N'',''N''-diisobutyltryptamine || >20&nbsp;mg || Unknown |- | 4-HO-DtBT || 4-Hydroxy''N'',''N''-di-''tert''-butyltryptamine || Unknown || Unknown |- | 4-HO-MET (metocin) || 4-Hydroxy-''N''-methyl-''N''-ethyltryptamine || 10–20&nbsp;mg (2–45&nbsp;mg+) || 4–6 hours |- | 4-HO-MPT (meprocin) || 4-Hydroxy-''N''-methyl-''N''-propyltryptamine || 8–30&nbsp;mg || Unknown |- | 4-HO-MiPT (miprocin) || 4-Hydroxy-''N''-methyl-''N''-isopropyltryptamine || 12–25&nbsp;mg (6–30&nbsp;mg) || 4–6 hours |- | 4-HO-MALT (maltocin) || 4-Hydorxy-''N''-methyl-''N''-allyltryptamine || Unknown || Unknown |- | 4-HO-MtBT || 4-Hydroxy-''N''-methyl-''N''-''tert''-butyltryptamine || >15&nbsp;mg || Unknown |- | 4-HO-EPT (eprocin) || 4-Hydroxy-''N''-ethyl-''N''-propyltryptamine || Unknown || Unknown |- | 4-HO-EiPT || 4-Hydroxy-''N''-ethyl-''N''-isopropyltryptamine || Unknown || Unknown |- | 4-HO-PiPT (piprocin) || 4-Hydroxy-''N''-propyl-''N''-isopropyltryptamine || Unknown || Unknown |- | 4-HO-TMT || 4-Hydroxy-''N'',''N'',''N''-trimethyltryptamine || Unknown || Unknown |- | Aeruginascin (4-PO-TMT) || 4-Phosphoryloxy-''N'',''N'',''N''-trimethyltryptamine || Unknown || Unknown |- | 4-HO-pyr-T || 4-Hydroxy-''N'',''N''-tetramethylenetryptamine || >20&nbsp;mg || Unknown |- class="sortbottom" | colspan="5" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Footnotes:''' ^a = Baeocystin has conflicting reports, some say that it's active and some say that it's inactive. ^b = Luvesilocin is known to be active subcutaneously at doses of 5 to 40{{nbsp}}mg with an average duration of 3.6{{nbsp}}hours. '''Refs:''' <ref name="JacobShulgin1994" /><ref name="Shulgin2003" /><ref name="TiHKAL" /><ref name="LuethiLiechti2018" /><ref name="HalberstadtChathaKlein2020" /><ref name="BallentineFriedmanBzdok2022" /><ref name="McKennaTowers1984" /><ref name="MallaroniMasonVinckenbosch2022" /> ''Individual:'' <ref name="LiechtiHolze2022" /><ref name="HolzeSinghLiechti2024" /><ref name="MalacaLoFaroTamborra2020">{{cite journal | vauthors = Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA | title = Toxicology and Analysis of Psychoactive Tryptamines | journal = International Journal of Molecular Sciences | volume = 21 | issue = 23 | page = 9279 | date = December 2020 | pmid = 33291798 | pmc = 7730282 | doi = 10.3390/ijms21239279 | quote = 4-OH-DPT is the 4-hydroxylated DPT derivative first synthesized by Shulgin et al. [82]. 4-OH-DPT is a light beige or white powder [54] that acts as a 5-HT2A partial agonist. 4-OH-DPT also shares structural similarity with psilocin [83]. Effects are dose dependent, with onset at 15–45 min and duration of 5–8 h. According to user reports, synthetic 4-OH-DPT produces visual effects and hallucinatory states [84]. | doi-access = free }}</ref><ref name="LudbrookBrysonTaylor2025">{{cite journal | vauthors = Ludbrook G, Bryson N, Taylor B, Hocevar-Trnka J, Johnson MW, Hirman J, Morrish G, Alexander R, Pollack M | title = Safety, Tolerability, Pharmacokinetics, and Pharmacodynamics of Subcutaneous RE104: A Double-Blind, Randomized, Single Ascending Dose Placebo-Controlled Study | journal = J Clin Psychopharmacol | volume = 45 | issue = 5 | pages = 441–453 | date = 2025 | pmid = 40685873 | pmc = 12379775 | doi = 10.1097/JCP.0000000000002047 | url = }}</ref><ref name="Aipsin-4-AcO-DMT">{{cite web | title=4-AcO-DMT (Ацетилпсилоцин) | website=АИПСИН | url=https://aipsin.com/newsubstance/671/ | language=ru | access-date=1 January 2026}}</ref> |}

===5-Hydroxytryptamines=== {{Sticky}} {| class="wikitable sortable sticky-header" |+ {{Nowrap|Oral doses and durations of 5-hydroxytryptamines}} |- ! Compound !! Chemical name !! Dose !! Duration |- | Serotonin (5-HT, 5-HO-T) || 5-Hydroxytryptamine || >100&nbsp;mg^a || – |- | ''N''-Methylserotonin (norbufotenin; 5-HO-NMT) || 5-Hydroxy-''N''-methyltryptamine || Unknown || Unknown |- | Bufotenin (5-HO-DMT) || 5-Hydroxy-''N'',''N''-dimethyltryptamine || >100&nbsp;mg^b || – |- | ''O''-Acetylbufotenin (5-AcO-DMT) || 5-Acetoxy-''N'',''N''-dimethyltryptamine || Unknown || Unknown |- | ''O''-Pivalylbufotenin (5-''t''-BuCO-DMT) || 5-Pivaloxy-''N'',''N''-dimethyltryptamine || Unknown || Unknown |- | 5-HO-DET || 5-Hydroxy-''N'',''N''-diethyltryptamine || Unknown || Unknown |- | 5-HO-DPT (DiPS, NDPS) || 5-Hydroxy-''N'',''N''-dipropyltryptamine || Unknown || Unknown |- | 5-HO-DiPT || 5-Hydroxy-''N'',''N''-diisopropyltryptamine || Unknown || Unknown |- | 5-HO-MET || 5-Hydroxy-''N''-methyl-''N''-ethyltryptamine || Unknown || Unknown |- | colspan="5" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Footnotes:''' ^a = Serotonin does not cross the blood–brain barrier and is not psychoactive. ^b = Bufotenin is not orally active, but is active intravenously at doses of 8 to 16{{nbsp}}mg with a duration of 1 to 2{{nbsp}}hours and is active via insufflation and other parenteral routes. '''Refs:''' <ref name="JacobShulgin1994" /><ref name="Shulgin2003" /><ref name="TiHKAL" /><ref name="McKennaTowers1984" /> ''Individual:'' <ref name="Ott2001a">{{cite journal | vauthors = Ott J | title = Pharmañopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine | journal = Journal of Psychoactive Drugs | volume = 33 | issue = 3 | pages = 273–281 | year = 2001 | pmid = 11718320 | doi = 10.1080/02791072.2001.10400574 | s2cid = 5877023 }}</ref><ref name="Ott2001b">{{cite book | vauthors = Ott J | chapter=Shamanic-Snuff Psychonautica: Pharmañopo: Bufotenine—Psychonautics | pages=99–116 (105–112, 114–115) | title=Shamanic Snuffs or Entheogenic Errhines | publisher=Entheobotanica | year=2001 | isbn=978-1-888755-02-2 | oclc=56061312 | url=https://books.google.com/books?id=AUP7NwAACAAJ | chapter-url=https://archive.org/details/vdocuments.mx_unknown-55b347d139b58/page/n51/mode/1up | access-date=24 January 2025 }}</ref><ref name="Morris2022">{{cite web | title=A New One-Hour Talk On 5-MeO-DMT | website=The Hamilton Morris Podcast | publisher=Patreon | host=Hamilton Morris | date=1 December 2022 | url=https://www.patreon.com/posts/new-one-hour-on-75373519 | access-date=21 January 2025 | time=6:27–8:40, 10:15–11:13 | quote=[Morris:] Bufotenine is a drug that I have tried. I've tried isolated pure bufotenine and it is a psychedelic that is both pharmacologically and experientially and chemically intermediate between DMT and 5-MeO-DMT. So it has a longer duration than actually both 5-MeO-DMT and DMT. It's yet less visual than DMT but more visual than 5-MeO-DMT, so it's kind of like in-between the two. It's also very nauseating, which is the main reason that people seem not to enjoy it very much. But it is a classical psychedelic drug that produces visionary effects. And Jonathan Ott actually liked the effect of it quite a bit. }}</ref><ref name="MorrisOtt2023">{{cite podcast | url=https://www.patreon.com/posts/podcast-28-talk-55653035 | title=PODCAST 28: A talk with Jonathan Ott | website=The Hamilton Morris Podcast | publisher=Patreon | host=Hamilton Morris | date=1 September 2021 | time=49:20–50:36 | access-date=20 January 2025 | quote=[Morris:] I've used [bufotenine] a couple times, once at 50 milligrams of the freebase snorted. [...] I found it to be extremely nauseating. I found it to be qualitatively intermediate between 5-MeO-DMT and DMT in that it was more visual than my experiences with 5-MeO-DMT but less visual than my typical experiences with DMT. It had a longer duration than 5-MeO-DMT and maybe even a longer duration than DMT as well. It was about an hour. Although I don't have all that much experience snorting DMT freebase. }}</ref> |}

===5-Methoxytryptamines=== {{Sticky}} {| class="wikitable sortable sticky-header" |+ {{Nowrap|Oral doses and durations of 5-methoxytryptamines}} |- ! Compound !! Chemical name !! Dose !! Duration |- | 5-MT (5-MeO-T) || 5-Methoxytryptamine || Unknown || Unknown |- | 5-MeO-NMT || 5-Methoxy-''N''-methyltryptamine || Unknown || Unknown |- | 5-MeO-NET || 5-Methoxy-''N''-ethyltryptamine || Unknown || Unknown |- | 5-MeO-NiPT || 5-Methoxy-''N''-isopropyltryptamine || Unknown || Unknown |- | 5-MeO-DMT (mebufotenin) || 5-Methoxy-''N'',''N''-dimethyltryptamine || >35&nbsp;mg^a || – |- | 5-MeO-DET || 5-Methoxy-''N'',''N''-diethyltryptamine || 1–3&nbsp;mg || 3–4 hours |- | 5-MeO-DPT || 5-Methoxy-''N'',''N''-dipropyltryptamine || 6–10&nbsp;mg || 2–4 hours |- | 5-MeO-DiPT || 5-Methoxy-''N'',''N''-diisopropyltryptamine || 6–12&nbsp;mg || 4–8 hours |- | 5-MeO-DALT || 5-Methoxy-''N'',''N''-diallyltryptamine || 12–25&nbsp;mg || 2–4 hours |- | 5-MeO-DBT || 5-Methoxy-''N'',''N''-dibutyltryptamine || Unknown || Unknown |- | 5-MeO-DsBT || 5-Methoxy-''N'',''N''-di-''sec''-butyltryptamine || Unknown || Unknown |- | 5-MeO-MET || 5-Methoxy-''N''-methyl-''N''-ethyltryptamine || Unknown || Unknown |- | 5-MeO-MPT || 5-Methoxy-''N''-methyl-''N''-propyltryptamine || Unknown || Unknown |- | 5-MeO-MiPT || 5-Methoxy-''N''-methyl-''N''-isopropyltryptamine || 4–6&nbsp;mg (0.5–20&nbsp;mg+) || 4–6 hours |- | 5-MeO-MALT || 5-Methoxy-''N''-methyl-''N''-allyltryptamine || Unknown || Unknown |- | 5-MeO-MsBT || 5-Methoxy-''N''-methyl-''N''-''sec''-butyltryptamine || 10–30&nbsp;mg || 3–4 hours |- | 5-MeO-EPT || 5-Methoxy-''N''-ethyl-''N''-propyltryptamine || Unknown || Unknown |- | 5-MeO-EiPT || 5-Methoxy-''N''-ethyl-''N''-isopropyltryptamine || Unknown || Unknown |- | 5-MeO-PiPT || 5-Methoxy-''N''-propyl-''N''-isopropyltryptamine || Unknown || Unknown |- | 5-MeO-iPALT (ASR-3001) || 5-Methoxy-''N''-isopropyl-''N''-allyltryptamine || 8–14&nbsp;mg || 1.5–2.5 hours |- | 5-MeO-pyr-T || 5-Methoxy-''N'',''N''-tetramethylenetryptamine || 0.5–2&nbsp;mg || Several hours |- | Melatonin (5-MeO-NAcT) || 5-Methoxy-''N''-acetyltryptamine || 1–10&nbsp;mg^b || A few hours |- |- class="sortbottom" | colspan="5" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Footnotes:''' ^a = 5-MeO-DMT is not orally active, but is active at a dose of 2 to 20&nbsp;mg smoked or 2 to 3{{nbsp}}mg intravenously, with a duration of 5 to 20{{nbsp}}minutes. Also orally active with an {{Abbrlink|MAOI|monoamine oxidase inhibitor}} at doses of 10 to 25{{nbsp}}mg. ^b = Melatonin is not a psychedelic but a hypnotic and is non-hallucinogenic at doses of up to 1,200{{nbsp}}mg. '''Refs:''' <ref name="JacobShulgin1994" /><ref name="Shulgin2003" /><ref name="TiHKAL" /><ref name="LuethiLiechti2018" /><ref name="HalberstadtChathaKlein2020" /><ref name="BallentineFriedmanBzdok2022" /><ref name="McKennaTowers1984" /> ''Individual:'' <ref name="HolzeSinghLiechti2024" /><ref name="Ott1999" /><ref name="Aipsin-5-MeO-MsBT">{{cite web | title=5-MeO-MsBT (5-methoxy-N-methyl-N-secbutyltryptamine) | website=АИПСИН | url=https://aipsin.com/newsubstance/987/ | language=ru | access-date=2 January 2026}}</ref> |}

===α-Alkyltryptamines=== {{Sticky}} {| class="wikitable sortable sticky-header" |+ {{Nowrap|Oral doses and durations of α-alkyltryptamines}} |- ! Compound !! Chemical name !! Dose !! Duration |- | AMT (α-methyl-T; Indopan)^a || α-Methyltryptamine || 15–40&nbsp;mg || 12–16 hours |- | AET (α-ethyl-T; etryptamine; Monase)^b || α-Ethyltryptamine || 100–160&nbsp;mg || 6–8 hours |- | α,''N''-DMT (''N''-methyl-AMT)^c || α-Methyl-''N''-methyltryptamine || 50–100&nbsp;mg || 6–8 hours |- | α,''N'',''N''-TMT (''N'',''N''-dimethyl-AMT) || α,''N'',''N''-Trimethyltryptamine || Unknown^d || Unknown |- | 2,α-DMT (2-methyl-AMT) || 2-Methyl-α-methyltryptamine || 300–500&nbsp;mg || 7–10 hours |- | 4-HO-AMT (MP-14) || 4-Hydroxy-α-methyltryptamine || 15–20&nbsp;mg+ || Unknown |- | 4-Methyl-AMT (MP-809) || 4-Methyl-α-methyltryptamine || 20–60&nbsp;mg+ || Unknown |- | 5-Fluoro-AMT (PAL-212, PAL-544) || 5-Fluoro-α-methyltryptamine || 25&nbsp;mg+ || >9 hours |- | 5-Chloro-AMT (PAL-542) || 5-Chloro-α-methyltryptamine || Unknown || Unknown |- | 5-Fluoro-AET (PAL-545) || 5-Fluoro-α-ethyltryptamine || Unknown || Unknown |- | 5-Chloro-AET (PAL-526) || 5-Chloro-α-ethyltryptamine || Unknown || Unknown |- | 6-Fluoro-AMT || 6-Fluoro-α-methyltryptamine || 25–75&nbsp;mg || "Long" |- | α-Methylserotonin (AMS; 5-HO-AMT) || α-Methyl-5-hydroxytryptamine || Unknown || Unknown |- | α,''O''-DMS (5-MeO-AMT) || α-Methyl-5-methoxytryptamine || 2.5–5&nbsp;mg (0.5–15&nbsp;mg) || 12–18 hours |- | ''α'',''N'',''O''-TMS (5-MeO-''N''-methyl-AMT) || α-Methyl-5-methoxy-''N''-methyltryptamine || 10–20&nbsp;mg || 6–8 hours |- | α,''N'',''N'',''O''-TeMS (5-MeO-''N'',''N''-dimethyl-AMT) || 5-Methoxy-α,''N'',''N''-trimethyltryptamine || Unknown || Unknown |- | 5-MeO-AET || α-Ethyl-5-methoxytryptamine || ~70&nbsp;mg || Several hours |- | Bk-NM-AMT (β-keto-''N''-methyl-AMT)^e || α-Methyl-β-keto-''N''-methyltryptamine || Unknown || Unknown |- |- class="sortbottom" | colspan="5" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Footnotes:''' ^a = AMT is a not only a psychedelic but is also a stimulant and entactogen. ^b = AET is an entactogen and stimulant and is not a psychedelic. ^c = α,''N''-DMT is a stimulant and is not a psychedelic or entactogen. ^d = α,''N'',''N''-TMT has been reported to be an active psychedelic orally but to be much less potent than AMT. ^e = Bk-NM-AMT is expected to be an entactogen and stimulant but not a psychedelic. '''Refs:''' <ref name="JacobShulgin1994" /><ref name="Shulgin2003" /><ref name="TiHKAL" /><ref name="LuethiLiechti2018" /><ref name="HalberstadtChathaKlein2020" /><ref name="McKennaTowers1984" /> ''Individual:'' <ref name="ThisLandPress2013">{{cite web |title= Unusual Analogues: Drugs Used by Gordon Todd Skinner |url= http://thislandpress.com/2013/07/25/unusual-analogues-drugs-used-by-gordon-todd-skinner/ | archive-url=https://web.archive.org/web/20160417235026/http://thislandpress.com/2013/07/25/unusual-analogues-drugs-used-by-gordon-todd-skinner/ | archive-date =17 April 2016 | website= thislandpress.com |publisher=This Land Press |access-date=8 April 2016}}</ref><ref name="Morris2025">{{cite podcast | url=https://www.patreon.com/posts/pod-126-return-122831707 | title=POD 126: The Return of Psychedelic Selenium with Dr. Josh Hartsel | website=The Hamilton Morris Podcast | publisher=Patreon | host=Hamilton Morris | date=29 April 2025 | time=1:33:53–1:35:50 | quote=[...] [Hartsel:] The α,''N'',''N''-Dimethyl[tryptamine]. [Morris:] Oh yeah, I've made it and tried it actually. [Hartsel:] Oh you did? [Morris:] Yeah, yeah. [Hartsel:] Oh, well what did it do? [Morris:] It is active, it's an active psychedelic. It's reduced potency. I never got it to a dose where it produced particularly interesting effects. I can look up the exact dose. I think it was like... the only thing I remember is that I felt like it was making me sneeze a lot. But it was very pleasant. Nothing bad happened. But the dose just wasn't high enough. I think I took maybe 40 mg. So it was much less potent than AMT orally. The other issue of course is that it could be a prodrug of ''N''-methyl-AMT, which is active, or AMT itself maybe. [...]}}</ref> |}

===Other tryptamines=== {{Sticky}} {| class="wikitable sortable sticky-header" |+ {{Nowrap|Oral doses and durations of other tryptamines}} |- ! Compound !! Chemical name !! Dose !! Duration |- | Lespedamine (1-MeO-DMT) || 1-Methoxy-''N'',''N''-dimethyltryptamine || Unknown || Unknown |- | 2-Methyl-DMT || 2-Methyl-''N'',''N''-dimethyltryptamine || 50–100&nbsp;mg || 4–6 hours |- | 2-Methyl-DET || 2-Methyl-''N'',''N''-diethyltryptamine || 80–120&nbsp;mg || 6–8 hours |- | 4-MeO-DMT || 4-Methoxy-''N'',''N''-dimethyltryptamine || Unknown || Unknown |- | 4-MeO-DET || 4-Methoxy-''N'',''N''-diethyltryptamine || >30&nbsp;mg || Unknown |- | 4-MeO-DiPT || 4-Methoxy-''N'',''N''-diisopropyltryptamine || Unknown || Unknown |- | 4-MeO-MiPT || 4-Methoxy-''N''-methyl-''N''-isopropyltryptamines || 20–30&nbsp;mg || 4–6 hours |- | 4,5-MDO-DMT || 4,5-Methylenedioxy-''N'',''N''-dimethyltryptamine || Unknown || Unknown |- | 4,5-MDO-DiPT || 4,5-Methylenedioxy-''N'',''N''-diisopropyltryptamine || >25&nbsp;mg || Unknown |- | 5-Fluoro-DMT || 5-Fluoro-''N'',''N''-dimethyltryptamine || Unknown || Unknown |- | 5-Chloro-DMT || 5-Chloro-''N'',''N''-dimethyltryptamine || Unknown || Unknown |- | 5-Bromo-DMT || 5-Bromo-''N'',''N''-dimethyltryptamine || Unknown^a || Unknown |- | Bretisilocin (5-fluoro-MET) || 5-Fluoro-''N''-methyl-''N''-ethyltryptamine || Unknown^b || Unknown^b |- | 5-MeO-2-TMT || 5-Methoxy-2-methyl-''N'',''N''-dimethyltryptamine || 75–150&nbsp;mg || 5–10 hours |- | 5-MeS-DMT || 5-Methylthio-''N'',''N''-dimethyltryptamine || Unknown^c || Unknown^c |- | 5,6-MeO-MiPT || 5,6-Dimethoxy-''N''-methyl-''N''-isopropyltryptamine || >75&nbsp;mg || Unknown |- | 5,6-MDO-DMT || 5,6-Methylenedioxy-''N'',''N''-dimethyltryptamine || >5&nbsp;mg || Unknown |- | 5,6-MDO-DiPT || 5,6-Methylenedioxy-''N'',''N''-diisopropyltryptamine || Unknown || Unknown |- | 5,6-MDO-MiPT || 5,6-Methylenedioxy-''N''-methyl-''N''-isopropyltryptamine || >50–60&nbsp;mg || Unknown |- | 6-Fluoro-DMT || 6-Fluoro-''N'',''N''-dimethyltryptamine || Unknown || Unknown |- | 6-Fluoro-DET || 6-Fluoro-''N'',''N''-diethyltryptamine || >80&nbsp;mg || Unknown |- | 6-HO-DMT || 6-Hydroxy-''N'',''N''-dimethyltryptamine || >80&nbsp;mg || Unknown |- | 6-HO-DET || 6-Hydroxy-''N'',''N''-diethyltryptamine || ≥10&nbsp;mg^d || 3–4 hours^d |- | 6-MeO-DMT || 6-Methoxy-''N'',''N''-dimethyltryptamine || Unknown || Unknown |- | 6-MeO-DiPT || 6-Methoxy-''N'',''N''-diisopropyltryptamine || >50&nbsp;mg || Unknown |- | 6-MeO-MiPT || 6-Methoxy-''N''-methyl-''N''-isopropyltryptamine || >50&nbsp;mg || Unknown |- | 7-HO-DMT || 7-Hydroxy-''N'',''N''-dimethyltryptamine || Unknown || Unknown |- | 7-MeO-DMT || 7-Methoxy-''N'',''N''-dimethyltryptamine || Unknown || Unknown |- | 7-MeO-DiPT || 7-Methoxy-''N'',''N''-diisopropyltryptamine || >70&nbsp;mg || Unknown |- | 7-MeO-MiPT || 7-Methoxy-''N''-methyl-''N''-isopropyltryptamine || >70&nbsp;mg || Unknown |- |- class="sortbottom" | colspan="5" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Footnotes:''' ^a = 5-Bromo-DMT is active via smoking at a dose of 20 to 50{{nbsp}}mg. ^b = Bretisilocin is active intravenously with a dose range of 10 to 20{{nbsp}}mg and a duration of 60 to 90{{nbsp}}minutes. ^c = 5-MeS-DMT's oral dose and duration are unknown, but smoked the dose is 15 to 30{{nbsp}}mg and the duration is 10 to 30{{nbsp}}minutes or <1 hour. ^d = Controversial and uncertain. '''Refs:''' <ref name="JacobShulgin1994" /><ref name="Shulgin2003" /><ref name="TiHKAL" /><ref name="BallentineFriedmanBzdok2022" /><ref name="McKennaTowers1984" /> ''Individual:'' <ref name="MorrisWallach2013">{{cite web | url=https://www.vice.com/en/article/sea-dmt-000481-v20n3/ | title=Sea DMT: God Molecule or Barnacle Repellent? | publisher=Vice | date=26 March 2013 | access-date=21 October 2015 | vauthors = Morris H, Wallach J }}</ref><ref name="MarekMakai-BölöniUmbricht2025">Marek GJ, Makai-Bölöni S, Umbricht D, Christian EP, Winters J, Dvorak D, Raines S, Hughes ZA, Austin EW, Klein AK, Leong W, Krol FJ, Graaf AJV, Juachon MJ, Otto ME, Borghans LGJM, Jacobs G, Kruegel AC, Sporn J. A novel psychedelic 5-HT2A receptor agonist GM-2505: The pharmacokinetic, safety, and pharmacodynamic profile from a randomized trial healthy volunteer. ''J Psychopharmacol''. 2025 Oct 16:2698811251378512. {{doi|10.1177/02698811251378512}} {{PMID|41099491}}</ref><ref name="SzaraHearst1962">{{cite journal | last1=Szara | first1=Stephen | last2=Hearst | first2=Eliot | title=The 6-Hydroxylation of Tryptamines Derivatives: A Way of Producing Psychoactive Metabolites | journal=Annals of the New York Academy of Sciences | volume=96 | issue=1 | date=1962 | issn=0077-8923 | doi=10.1111/j.1749-6632.1962.tb50108.x | pages=134–141 | bibcode=1962NYASA..96..134S | url= | quote=This correlation between metabolic transformation rates and psychological effect is suggestive. It strengthens our notion that metabolically formed 6-HDET most likely plays a role in producing the psychological effects. A more stringent test would be to give the metabolite directly to the same subjects, as was done in the animal experiments. Unfortunately we did not have enough synthetic 6-HDET to do extensive human studies, so the senior author tried it out himself. Both 1 and 2 mg. of 6-HDET had no noticeable effect. At 5 mg. there was only a very faint short-lasting perceptual disturbance. Then, on the fourth attempt, 10 mg. of 6-HDET was administered. No obvious effect on behavior occurred in the first hour, but then typical psychotomimetic disturbances began to appear. For the next 2 or 3 hours hallucinogenic effects were observed that were very similar to the effect of 60 mg. of DET. These experiments lead us to believe that 6-HDET in man is 5 to 6 times more active psychotropically than DET, but more extended studies will be necessary to establish the exact form of the relationship.}}</ref> |}

==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

==Pharmacology== ===Pharmacodynamics=== {{Sticky}} {| class="wikitable sticky-header" |+ {{Nowrap|Serotonin receptor affinities (K_i, nM) of selected psychedelic tryptamines (Jain et al., 2025)<ref name="JainGumpperSlocum2025">{{cite journal | vauthors = Jain MK, Gumpper RH, Slocum ST, Schmitz GP, Madsen JS, Tummino TA, Suomivuori CM, Huang XP, Shub L, DiBerto JF, Kim K, DeLeon C, Krumm BE, Fay JF, Keiser M, Hauser AS, Dror RO, Shoichet B, Gloriam DE, Nichols DE, Roth BL | title = The polypharmacology of psychedelics reveals multiple targets for potential therapeutics | journal = Neuron | volume = 113| issue = 19| pages = 3129–3142.e9| date = July 2025 | pmid = 40683247 | doi = 10.1016/j.neuron.2025.06.012 | url = https://www.cell.com/cms/10.1016/j.neuron.2025.06.012/attachment/7d8365fe-51f3-4a28-bf40-9999bec837f6/mmc11.pdf}}</ref>}} |- ! Compound !! 5-HT_1A !! 5-HT_1B !! 5-HT_1D !! 5-HT_1E !! 5-HT_2A !! 5-HT_2B !! 5-HT_2C !! 5-HT₃ !! 5-HT_5A !! 5-HT₆ !! 5-HT₇ !! SERT |- | DMT || 269 || 447 || 117 || 380 || 380 || 112 || 257 || – || 2,090 || 275 || 69 || 2,400 |- | Psilocin || 372 || 191 || 98 || 339 || 200 || 25 || 245 || – || 447 || 79 || 87 || 2,570 |- | Psilocybin || 5,250 || – || 195 || – || 851 || 479 || 3,090 || – || – || 776 || – || – |- | 4-AcO-MALT || 977 || – || 871 || 417 || 692 || 25 || 631 || – || – || 661 || 794 || 3,090 |- | Bufotenin || 8.3 || 59 || 22 || 25 || 224 || 6.2 || 209 || 166 || 302 || 18 || 8.9 || 1,120 |- | 5-MeO-DMT || 10 || 91 || 21 || 575 || 200 || 15 || 490 || – || 589 || 25 || 4.4 || – |- | 5-MeO-DiPT || 170 || – || 871 || – || 324 || 46 || – || – || – || 2,190 || – || – |- | 5-MeO-DALT || 17 || 1,020 || 54 || 977 || 457 || 100 || 2,240 || – || – || 162 || 60 || 4,470 |- | 5-MeO-EiPT || 54 || 1,170 || 174 || – || 1,622 || 98 || – || – || – || 407 || 661 || 5,620 |- | LSD || 5.9 || 21 || 3.5 || 135 || 8.5 || 5.5 || 17 || – || 1.8 || 16 || 8.5 || – |}

{{Sticky}} {| class="wikitable sticky-header" |+ {{Nowrap|Serotonin receptor affinities (K_i, nM) of selected psychedelic tryptamines (Ray, 2010)<ref name="Ray2010">{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | article-number = e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | bibcode = 2010PLoSO...5.9019R | doi-access = free | url = }}</ref>}} |- ! Compound !! 5-HT_1A !! 5-HT_1B !! 5-HT_1D !! 5-HT_1E !! 5-HT_2A !! 5-HT_2B !! 5-HT_2C !! 5-HT₃ !! 5-HT_5A !! 5-HT₆ !! 5-HT₇ !! SERT |- | DMT || >10,000 || >10,000 || 93 || 456 || 2,323 || 108 || 335 || >10,000 || 611 || 487 || 883 || 3,742 |- | DPT || 32 || 854 || 619 || 2,338 || 2,579 || 42 || 1,567 || >10,000 || 4,373 || 4,543 || 284 || 157 |- | DiPT || 121 || >10,000 || 3,742 || >10,000 || >10,000 || 399 || >10,000 || >10,000 || >10,000 || >10,000 || 3,423 || 1,258 |- | Psilocin || 63 || 305 || 19 || 44 || 340 || 4.7 || 141 || >10,000 || 70 || 72 || 72 || 852 |- | 5-MeO-DMT || 1.9 || 74 || 6.3 || 360 || 2,011 || 3,884 || 538 || >10,000 || 277 || 36 || 3.9 || 2,032 |- | 5-MeO-DiPT || 132 || 5,137 || 1,718 || >10,000 || >10,000 || 163 || >10,000 || >10,000 || >10,000 || >10,000 || 1,231 || 2,531 |- | 5-MeO-MiPT || 12 || 303 || 23 || 3,496 || 448 || 59 || 2,186 || >10,000 || 953 || 130 || 20 || 6,409 |- | 6-Fluoro-DMT || 393 || 218 || 55 || 461 || 866 || 30 || 674 || >10,000 || 961 || 26 || 41 || 145 |- | 5-MeO-2-TMT<!-- (2-Me-5-MeO-DMT)--> || 200 || >10,000 || 250 || 1,800 || >10,000 || ? || 4,020 || ? || 10,450 || 60 || 145 || >10,000 |- | EMDT<!-- (2-Et-5-MeO-DMT)--> || 170 || >10,000 || 290 || 520 || >10,000 || ? || 1,810 || ? || 4,620 || 16 || 300 || >10,000 |- | Ibogaine || >10,000 || >10,000 || >10,000 || ? || 14,142 || ? || >10,000 || >10,000 || ? || ? || ? || 549 |- | LSD || 7.3 || 3.9 || 7.8 || 93 || 11 || 30 || 31 || >10,000 || 9 || 6.9 || 6.6 || >10,000 |}

==Chemistry== ===Synthesis=== The chemical syntheses of numerous tryptamines have been described by Alexander Shulgin in his book ''TiHKAL'' (''Tryptamines I Have Known and Loved'').<ref name="TiHKAL" /> A well-known and widely used synthetic approach for making tryptamines is the Speeter–Anthony route, which starts with indole.<ref name="Collins2011">{{cite journal | vauthors = Collins M | title = Some new psychoactive substances: precursor chemicals and synthesis-driven end-products | journal = Drug Test Anal | volume = 3 | issue = 7–8 | pages = 404–416 | date = 2011 | pmid = 21755608 | doi = 10.1002/dta.315 | url = }}</ref><ref name="AppendinoMinassiTaglialatela-Scafati2014">{{cite journal | vauthors = Appendino G, Minassi A, Taglialatela-Scafati O | title = Recreational drug discovery: natural products as lead structures for the synthesis of smart drugs | journal = Nat Prod Rep | volume = 31 | issue = 7 | pages = 880–904 | date = July 2014 | pmid = 24823967 | doi = 10.1039/c4np00010b | url = }}</ref><ref name="Shaba2020">{{cite web | last=Shaba | first=Reham | title=Development of an improved psilocybin synthesis | website=DIVA | date=24 September 2020 | url=https://www.diva-portal.org/smash/record.jsf?pid=diva2%3A1470170&dswid=-3583 | access-date=9 November 2025}}</ref> Other tryptamine synthesis routes have also been described, for instance starting with tryptamine rather than indole.<ref name="Collins2011" /><ref name="AppendinoMinassiTaglialatela-Scafati2014" /> The chemical syntheses of the psychedelic tryptamines bufotenin (5-HO-DMT) and 5-MeO-DMT (mebufotenin) have been comprehensively reviewed.<ref name="HomonLaramieHayward2026">{{cite journal | vauthors = Homon A, Laramie J, Hayward JJ, Trant JF | title = We Licked the Toads so You Don't Have to: A Comprehensive Analysis of the Chemical Syntheses of the Classical Psychedelics Bufotenin(e) and 5-Methoxy-N,N-Dimethyltryptamine | journal = ChemMedChem | volume = 21 | issue = 4 | article-number = e202500525 | date = February 2026 | pmid = 41765690 | doi = 10.1002/cmdc.202500525 | url = | doi-access = free }}</ref>

==List of substituted tryptamines== {{Incomplete list|date=October 2021}} {{Sticky}} {| class="wikitable sortable sticky-header" style="font-size: small;" |- ! Structure ! Name ! Origin ! Ring sub. ! R^N1 ! R^N2 ! width="50px" | Chemical name ! CAS # |- | 130px|class=skin-invert-image || Tryptamine (T) || Animals, plants, fungi || H || H || H || 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine || 61-54-1 |- | 120px|class=skin-invert-image || ''N''-Methyltryptamine (NMT) || Plants || H || H || CH₃ || ''N''-methyltryptamine || 61-49-4 |- | 120px|class=skin-invert-image || 2-HO-NMT || Plants || 2-OH || H || CH₃ || 2-hydroxy-''N''-methyltryptamine || 106987-89-7 |- | 120px|class=skin-invert-image || 5-MeO-NMT || Plants || 5-OCH₃ || H || CH₃ || 5-methoxy-''N''-methyltryptamine || 2009-03-2 |- | 120px|class=skin-invert-image || Serotonin (5-HT) || Animals, plants || 5-OH || H || H || 5-hydroxytryptamine || 50-67-9 |- | 120px|class=skin-invert-image || ''N''-Methylserotonin (NMS; norbufotenin; 5-HO-NMT) || Plants || 5-OH || H || CH₃ || 5-hydroxy-''N''-methyltryptamine || 1134-01-6 |- | 120px|class=skin-invert-image || Bufotenin (5-HO-DMT) || Animals, plants, fungi || 5-OH || CH₃ || CH₃ || 5-hydroxy-''N'',''N''-dimethyltryptamine || 487-93-4 |- | 120px|class=skin-invert-image || Bufotenidine (5-HTQ) || Amphibians || 5-O⁻ || colspan=2 | (CH₃)₃ || 3-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate || 487-91-2 |- | 120px|class=skin-invert-image || Bufoviridine (5-SO-DMT) || Amphibians || 5-SO || CH₃ || CH₃ || 5-sulfooxy-''N'',''N''-dimethyltryptamine || 16369-08-7 |- | 120px|class=skin-invert-image || 5-Methoxytryptamine (5-MT; 5-MeO-T) || Animals, plants || 5-OCH₃ || H || H || 5-methoxytryptamine || 608-07-1 |- | 120px|class=skin-invert-image || Melatonin (5-MeO-NAcT) || Animals, plants, microbes || 5-OCH₃ || H || O=C-CH₃ || 5-methoxy-''N''-acetyltryptamine || 73-31-4 |- | 120px|class=skin-invert-image || ''N''-Acetylserotonin (NAS; normelatonin; 5-HO-NAcT) || Animals || 5-OH || H || O=C-CH₃ || 5-hydroxy-''N''-acetyltryptamine || 1210-83-9 |- | 120px|class=skin-invert-image || 6-Hydroxymelatonin || Animals || 5-OCH₃, 6-OH || H || O=C-CH₃ || ''N''-[2-(6-Hydroxy-5-methoxy-1''H''-indol-3-yl)ethyl]acetamide || 2208-41-5 |- | 120px|class=skin-invert-image || 4-Hydroxytryptamine (4-HT) || Fungi || 4-OH || H || H || 4-hydroxytryptamine || 570-14-9 |- | 120px|class=skin-invert-image || 4-HO-NMT || Fungi || 4-OH || H || CH₃ || 4-hydroxy-''N''-methyltryptamine || 28363-70-4 |- | 120px|class=skin-invert-image || Psilocin (4-HO-DMT) || Fungi || 4-OH || CH₃ || CH₃ || 4-hydroxy-''N'',''N''-dimethyltryptamine || 520-53-6 |- | 120px|class=skin-invert-image || 4-HO-TMT || Fungi || 4-OH || CH₃ || CH₃ || 4-hydroxy-''N'',''N'',''N''-trimethyltryptammonium || 262285-41-6 |- | 120px|class=skin-invert-image || Norbaeocystin (4-PO-T) || Fungi || 4-OPO₃H₂ || H || H || 4-phosphoryloxy-tryptamine || 21420-59-7 |- | 120px|class=skin-invert-image || Baeocystin (4-PO-NMT) || Fungi || 4-OPO₃H₂ || H || CH₃ || 4-phosphoryloxy-''N''-methyl-tryptamine || 21420-58-6 |- | 120px|class=skin-invert-image || Psilocybin (4-PO-DMT) || Fungi || 4-OPO₃H₂ || CH₃ || CH₃ || 4-phosphoryloxy-''N'',''N''-dimethyltryptamine || 520-52-5 |- | 120px|class=skin-invert-image || Aeruginascin (4-PO-TMT) || Fungi || 4-OPO₃H₂ || colspan=2 | (CH₃)₃ || [3-[2-(trimethylazaniumyl)ethyl]-1''H''-indol-4-yl] hydrogen phosphate || 114264-95-8 |- | 120px|class=skin-invert-image || Dimethyltryptamine (DMT) || Animals, plants || H || CH₃ ||CH₃ || ''N'',''N''-dimethyltryptamine || 61-50-7 |- | 120px|class=skin-invert-image || Lespedamine (1-MeO-DMT) || Plants || 1-OCH₃ || CH₃ || CH₃ || 1-methoxy-''N'',''N''-dimethyltryptamine || 4335-93-7 |- | 120px|class=skin-invert-image || 5-MeO-DMT (mebufotenin) || Animals, plants || 5-OCH₃ || CH₃ || CH₃ || 5-methoxy-''N'',''N''-dimethyltryptamine || 1019-45-0 |- | 120px|class=skin-invert-image || 5-Bromo-DMT || Marine sponges, invertebrates || 5-Br || CH₃ || CH₃ || 5-bromo-''N'',''N''-dimethyltryptamine || 17274-65-6 |- | 120px|class=skin-invert-image || 6-Bromotryptamine || Marine invertebrates || 6-Br || H || H || 6-bromotryptamine || 96624-18-9 |- | 120px|class=skin-invert-image || 5,6-Dibromotryptamine || Marine invertebrates || 5,6-Br || H || H || 5,6-dibromotryptamine || |- | 120px|class=skin-invert-image || 5,6-Dibromo-NMT || Marine invertebrates || 5,6-Br || H || CH₃ || 5,6-dibromo-''N''-methyltryptamine || |- | 120px|class=skin-invert-image || 5,6-Dibromo-DMT || Marine sponges, invertebrates || 5,6-Br || CH₃ || CH₃ || 5,6-dibromo-''N'',''N''-dimethyltryptamine || 72853-80-6 |- | 120px|class=skin-invert-image || Desformylflustrabromine (dFBr) || Marine invertebrates || 2-(α,α-dimethylallyl), 6-Br || H || CH₃ || 2-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine || 474657-72-2 |- | 120px|class=skin-invert-image || Convolutindole A || Marine invertebrates || 2,4,6-Br, 1,7-OCH₃ || CH₃ || CH₃ || 1,7-dimethoxy-2,4,6-tribromo-''N'',''N''-dimethyltryptamine || 443356-86-3 |- | 130px|class=skin-invert-image || α,α-Dideuterotryptamine<ref>{{cite web | title=1,1-dideuterio-2-(1H-indol-3-yl)ethanamine | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/10654563 | access-date=26 May 2026}}</ref> || artificial || H || H || H || α,α-Dideuterotryptamine || ? |- | 130px|class=skin-invert-image || β,β-Dideuterotryptamine<ref>{{cite web | title=2,2-dideuterio-2-(1H-indol-3-yl)ethanamine | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/12238690 | access-date=26 May 2026}}</ref> || artificial || H || H || H || β,β-Dideuterotryptamine || ? |- | 120px|class=skin-invert-image || 1-Methyltryptamine (1-MT) | artificial | 1-CH₃ | H | H | 1-Methyltryptamine | 7518-21-0 |- | 120px|class=skin-invert-image || 4-Methoxytryptamine (4-MeO-T) | artificial | 4-OCH₃ | H | H | 4-Methoxytryptamine | 3610-35-3 |- | 120px|class=skin-invert-image || 4-Fluorotryptamine (4-FT) | artificial | 4-F | H | H | 4-Fluorotryptamine | 467452-26-2 |- | 120px|class=skin-invert-image || 5-Methoxytryptamine-α,α,β,β-d4 (5-MT-d4)<ref>{{cite web | title=5-METHOXYTRYPTAMINE-alpha,alpha,beta,beta-D4 | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/12273662 | access-date=26 May 2026}}</ref> | artificial | 5-OCH₃ | H | H | α,α,β,β-Tetradeutero-5-methoxytryptamine | 96236-05-4 |- | 120px|class=skin-invert-image || 5-Methyltryptamine (5-MT) | artificial | 5-CH₃ | H | H | 5-Methyltryptamine | 1821-47-2 |- | 120px|class=skin-invert-image || 5-Fluorotryptamine (5-FT) | artificial | 5-F | H | H | 5-Fluorotryptamine | 576-16-9 |- | 120px|class=skin-invert-image || 5-Chlorotryptamine (5-Cl-T) | artificial | 5-Cl | H | H | 5-Chlorotryptamine | 3764-94-1 |- | 120px|class=skin-invert-image || 5-Bromotryptamine (5-Br-T) | artificial | 5-Br | H | H | 5-Bromotryptamine | 3610-42-2 |- | 120px|class=skin-invert-image || 6-Methyltryptamine (6-MT) | artificial | 6-CH₃ | H | H | 6-Methyltryptamine | 62500-90-7 |- | 120px|class=skin-invert-image || 6-Hydroxytryptamine (6-HT) | artificial | 6-OH | H | H | 6-Hydroxytryptamine | 443-31-2 |- | 120px|class=skin-invert-image || 6-Methoxytryptamine (6-MeO-T) | artificial | 6-OCH₃ | H | H | 6-Methoxytryptamine | 3610-36-4 |- | 120px|class=skin-invert-image || 6-Fluorotryptamine (6-FT) | artificial | 6-F | H | H | 6-Fluorotryptamine | 575-85-9 |- | 120px|class=skin-invert-image || 7-Methyltryptamine (7-MT) | artificial | 7-CH₃ | H | H | 7-Methyltryptamine | 14490-05-2 |- | 120px|class=skin-invert-image || 7-Hydroxytryptamine (7-HT) | artificial | 7-OH | H | H | 7-Hydroxytryptamine | 15700-23-9 |- | 120px|class=skin-invert-image || 7-Methoxytryptamine (7-MeO-T) | artificial | 7-OCH₃ | H | H | 7-Methoxytryptamine | 2436-04-6 |- | 120px|class=skin-invert-image || 7-Fluorotryptamine (7-F-T) | artificial | 7-F | H | H | 7-Fluorotryptamine | 191927-74-9 |- | 120px|class=skin-invert-image || 7-Chlorotryptamine (7-Cl-T) | artificial | 7-Cl | H | H | 7-Chlorotryptamine | 3804-16-8 |- | 120px|class=skin-invert-image || Acetryptine (5-acetyltryptamine; 5-AT) | artificial | 5-COCH₃ | H | H | 5-Acetyltryptamine | 3551-18-6 |- | 130px|class=skin-invert-image || 5-Phenoxytryptamine (5-PhO-T) | artificial | 5-OC₆H₅ | H | H | 5-Phenoxytryptamine | 31363-70-9 |- | 130px|class=skin-invert-image || 5-Benzyloxytryptamine (5-BT) | artificial | 5-OCH₂C₆H₅ | H | H | 5-Benzyloxytryptamine | 20776-45-8 |- | 120px|class=skin-invert-image || 5-Carboxamidotryptamine (5-CT) | artificial | 5-CONH₂ | H | H | 5-Carboxamidotryptamine | 74885-09-9 |- | 120px|class=skin-invert-image || 5-Nitrotryptamine (Nitro-I) | artificial | 5-NO₂ | H | H | 5-Nitrotryptamine | 55747-72-3 |- | 130px|class=skin-invert-image || 5-(Nonyloxy)tryptamine (5-NOT) || artificial || 5-O(CH₂)₈CH₃ || H || H || 5-Nonyloxytryptamine || 157798-12-4 |- | 120px|class=skin-invert-image || 2-Methyl-5-hydroxytryptamine | artificial | 2-CH₃, 5-OH | H | H | 3-(2-aminoethyl)-2-methyl-1''H''-indol-5-ol | 78263-90-8 |- | 120px|class=skin-invert-image || ''N''-Ethyltryptamine (NET) | artificial | H | H | CH₂CH₃ | N-ethyltryptamine | 61-53-0 |- | 120px|class=skin-invert-image || ''N''-Propyltryptamine (NPT) | artificial | H | H | CH₂CH₂CH₃ | N-propyltryptamine | |- | 120px|class=skin-invert-image || ''N''-Isopropyltryptamine (NiPT) | artificial | H | H | CH(CH₃)₂ | N-isopropyltryptamine | 14121-10-9 |- | 120px|class=skin-invert-image || ''N''-Cyclopropyltryptamine (NcPT) | artificial | H | H | C₃H₅ | N-cyclopropyltryptamine | |- | 120px|class=skin-invert-image || ''N''-''sec''-Butyltryptamine (NsBT) | artificial | H | H | CH(CH₃)CH₂CH₃ | N-''sec''-butyltryptamine | |- | 120px|class=skin-invert-image || ''N''-''tert''-Butyltryptamine (NtBT) | artificial | H | H | C(CH₃)₃ | N-[2-(1H-indol-3-yl)ethyl]-2-methylpropan-2-amine | 1344092-44-9 |- | 120px|class=skin-invert-image || ''N''-Amyltryptamine (NAT) | artificial | H | H | (CH₂)₄CH₃ | ''N''-[2-(1''H''-indol-3-yl)ethyl]pentan-1-amine | |- | 120px|class=skin-invert-image || ''N''-Hexyltryptamine (NHT) | artificial | H | H | (CH₂)₅CH₃ | ''N''-[2-(1''H''-indol-3-yl)ethyl]hexan-1-amine | |- | 120px|class=skin-invert-image || ''N''-(2-Cyanoethyl)tryptamine (CE-T) | artificial | H | H | CH₂CH₂C≡N | ''N''-(2-Cyanoethyl)tryptamine | 105115-85-3 |- | 130px|class=skin-invert-image || ''N''-Benzyltryptamine (NBnT) | artificial | H | H | CH₂C₆H₅ | ''N''-benzyltryptamine | 15741-79-4 |- | 130px|class=skin-invert-image || CPI-CG-8 | artificial | H | H | (2-Indolylethyl) | ''N''-Methyl-''N''-(2-indolylethyl)tryptamine | ? |- | 130px|class=skin-invert-image || T-NBOMe (NBOMeT) | artificial | H | H | CH₂C₆H₄(''o''-OCH₃) | ''N''-(2-methoxybenzyl)tryptamine | 418781-81-4 |- | 130px|class=skin-invert-image || 4-HO-NET | artificial | 4-OH | CH₂CH₃ | H | 4-hydroxy-''N''-ethyltryptamine | |- | 130px|class=skin-invert-image || 4-HO-NPT | artificial | 4-OH | CH(CH₃)₂ | H | 4-hydroxy-''N''-propyltryptamine | |- | 130px|class=skin-invert-image || 4-HO-NiPT | artificial | 4-OH | CH(CH₃)₂ | H | 4-hydroxy-''N''-isopropyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-NALT | artificial | 4-OH | H | H₂C=CH-CH₂ | 4-hydroxy-''N''-allyltryptamine | |- | 130px|class=skin-invert-image || 4-HO-NBT (4-HO-NnBT) | artificial | 4-OH | H | (CH₂)₃CH₃ | 4-hydroxy-''N''-''n''-butyltryptamine | |- | 130px|class=skin-invert-image || 4-HO-NiBT | artificial | 4-OH | H | CH₂CH(CH₃)₂ | 4-hydroxy-''N''-isobutyltryptamine | |- | 130px|class=skin-invert-image || 4-HO-NsBT | artificial | 4-OH | H | CH(CH₃)CH₂CH₃ | 4-hydroxy-''N''-''sec''-butyltryptamine | |- | 130px|class=skin-invert-image || 4-HO-NtBT | artificial | 4-OH | H | C(CH₃)₃ | 4-hydroxy-''N''-''tert''-butyltryptamine | |- | 130px|class=skin-invert-image || 4-HO-NBnT | artificial | 4-OH | H | CH₂C₆H₅ | 4-hydroxy-''N''-benzyltryptamine | |- | 130px|class=skin-invert-image || 1-Me-4-HO-T-NBOMe <ref>[https://patents.google.com/patent/WO2021179091A1/ Kozikowski A, et al. 3-(2-(aminoethyl)-indol-4-ol derivatives, methods of preparation thereof, and the use as 5-ht2 receptor modulators. Patent WO 2021/179091]</ref> | artificial | 1,Me, 4-OH | H | CH₂C₆H₄-''o''-OCH₃ | 1-methyl-4-hydroxy-''N''-(2-methoxybenzyl)tryptamine | |- | 130px|class=skin-invert-image || 4-HO-NcHT | artificial | 4-OH | H | C₆H₁₁ | 4-hydroxy-''N''-cyclohexyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-NET | artificial | 5-OCH₃ | H | CH₂CH₃ | 5-methoxy-''N''-ethyltryptamine | 1019-46-1 |- | 120px|class=skin-invert-image || 5-MeO-NiPT | artificial | 5-OCH₃ | H | CH(CH₃)₂ | 5-methoxy-''N''-isopropyltryptamine | 109921-55-3 |- | 130px|class=skin-invert-image || 5-MeO-NsBT | artificial | 5-OCH₃ | H | CH(CH₃)CH₂CH₃ | 5-methoxy-''N''-''sec''-butyltryptamine | |- | 130px|class=skin-invert-image || 5-MeO-NBnT | artificial | 5-OCH₃ | H | CH₂C₆H₅ | 5-methoxy-''N''-benzyltryptamine | 25100-31-6 |- | 130px|class=skin-invert-image || 5-MeO-T-NBOMe | artificial | 5-OCH₃ | H | CH₂C₆H₄(''o''-OCH₃) | 5-methoxy-''N''-(''ortho''-methoxybenzyl)tryptamine | 1335331-37-7 |- | 130px|class=skin-invert-image || 5-MeO-T-NB3OMe <ref name="pmid30629611">{{cite journal | vauthors = Toro-Sazo M, Brea J, Loza MI, Cimadevila M, Cassels BK | title = 5-HT2 receptor binding, functional activity and selectivity in N-benzyltryptamines | journal = PLOS ONE | volume = 14 | issue = 1 | article-number = e0209804 | date = 2019 | pmid = 30629611 | pmc = 6328172 | doi = 10.1371/journal.pone.0209804 | bibcode = 2019PLoSO..1409804T | doi-access = free }}</ref> | artificial | 5-OCH₃ | H | CH₂C₆H₄(''m''-OCH₃) | 5-methoxy-''N''-(''meta''-methoxybenzyl)tryptamine | 1648553-42-7 |- | 130px|class=skin-invert-image || 5-MeO-NBpBrT | artificial | 5-OCH₃ | H | CH₂C₆H₄(''p''-Br) | N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine | 155639-13-7 |- | 130px|class=skin-invert-image || 5-MeO-34MPEMT <ref name="Jensen2004">{{cite thesis | vauthors = Jensen N | title = Tryptamines as Ligands and Modulators of the Serotonin 5-HT2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens. | date = 2004 | url = https://isomerdesign.com/bitnest/external/Theses/Jensen2004 | degree = PhD | publisher = Georg-August-Universität zu Göttingen }}</ref> | artificial | 5-OCH₃ | CH₃ | CH₂CH₂C₆H₃(''p,m''-OCH₃) | N-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5-methoxy-1H-indol-3-yl)ethanamine | |- | 130px|class=skin-invert-image || Idalopirdine | artificial | 6-F | H | CH₂C₆H₄(''m''-OCH₂CF₂CF₂H) | 2-(6-Fluoro-1''H''-indol-3-yl)-''N''-(3-(2,2,3,3-tetrafluoro-propoxy)benzyl)ethanamine | 467459-31-0 |- | 130px|class=skin-invert-image || Z2876442907<ref name="pmid38187536">{{cite bioRxiv | vauthors = Lyu J, Kapolka N, Gumpper R, Alon A, Wang L, Jain MK, Barros-Álvarez X, Sakamoto K, Kim Y, DiBerto J, Kim K, Tummino TA, Huang S, Irwin JJ, Tarkhanova OO, Moroz Y, Skiniotis G, Kruse AC, Shoichet BK, Roth BL | display-authors = 6 | title = AlphaFold2 structures template ligand discovery | date = December 2023 | biorxiv = 10.1101/2023.12.20.572662 }}</ref> | artificial | 4-CH₃ | H | CH₂(C₃HNS)-COOCH₂CH₃ | ethyl 2-({[2-(4-methyl-1H-indol-3-yl)ethyl]amino}methyl)-1,3-thiazole-5-carboxylate | |- | 120px|class=skin-invert-image || Cis-2',5'-dimethyl-4-HO-azt-T <ref name="Towards unmakable psychedelics: S">{{cite journal | vauthors = Stirn J, Berger R, Hübner H, Gmeiner P, Klein CD | title = Towards "unmakable" psychedelics: SAR exploration of psilocin analogs obtained by a HATU-mediated amide coupling strategy | journal = European Journal of Medicinal Chemistry Reports | volume = 15 | article-number = 100278 | date = 2025 | doi = 10.1016/j.ejmcr.2025.100278 | doi-access = free }}</ref> || artificial || 4-OH || colspan=2 | ''cis''-(CHCH₃)CH₂(CHCH₃) || 3-{2-[(2R,4S)-2,4-dimethylazetidin-1-yl]ethyl}-1H-indol-4-ol || |- | 120px|class=skin-invert-image || Pyr-T || artificial || H || colspan=2 | (CH₂)₄ || 3-[2-(Pyrrolidin-1-yl)ethyl]-1''H''-indole || 14008-96-9 |- | 120px|class=skin-invert-image || 4-HO-pyr-T || artificial || 4-OH || colspan=2 | (CH₂)₄ || 3-[2-(Pyrrolidin-1-yl)ethyl]-1''H''-indol-4-ol || 63097-26-7 |- | 120px|class=skin-invert-image || Cis-2',5'-dimethyl-4-HO-pyr-T <ref name="Towards unmakable psychedelics: S"/> || artificial || 4-OH || colspan=2 | ''cis''-(CHCH₃)CH₂CH₂(CHCH₃) || 3-{2-[(2R,5S)-2,5-dimethylpyrrolidin-1-yl]ethyl}-1H-indol-4-ol || |- | 120px|class=skin-invert-image || 5-MeO-pyr-T || artificial || 5-OCH₃ || colspan=2 | (CH₂)₄ || 5-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1''H''-indole || 3949-14-2 |- | 120px|class=skin-invert-image || 4-F-5-MeO-pyr-T || artificial || 4-F-5-OCH₃ || colspan=2 | (CH₂)₄ || 4-Fluoro-5-methoxy-3-(2-pyrrolidin-1-ylethyl)-1''H''-indole || 344790-93-8 |- | 120px|class=skin-invert-image || Pip-T || artificial || H || colspan=2 | (CH₂)₅ || 3-(2-Piperidin-1-ylethyl)-1''H''-indole || 26628-87-5 |- | 120px|class=skin-invert-image || 5-MeO-pip-T || artificial || 5-OCH₃ || colspan=2 | (CH₂)₅ || 5-Methoxy-3-(2-piperidin-1-ylethyl)-1''H''-indole || |- | 120px|class=skin-invert-image || Mor-T || artificial || H || colspan=2 | ? || 3-[2-(Morpholin-4-yl)ethyl]-1''H''-indole || 25262-59-3 |- | 120px|class=skin-invert-image || 5-MeO-mor-T || artificial || 5-OCH₃ || colspan=2 | ? || 5-Methoxy-3-[2-(morpholin-4-yl)ethyl]-1''H''-indole || 3949-13-1 |- | 120px|class=skin-invert-image || IsoqT<ref>{{cite web | title=3-[2-(2-azabicyclo[2.2.2]octan-2-yl)ethyl]-1H-indole | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/53634044 | access-date=11 January 2026}}</ref> || artificial || H || colspan=2 | ? || 3-[2-(2-Azabicyclo[2.2.2]octan-2-yl)ethyl]-1''H''-indole || |- | 120px|class=skin-invert-image || 5-MeO-IsoqT || artificial || 5-OCH₃ || colspan=2 | ? || 3-[2-(2-Azabicyclo[2.2.2]octan-2-yl)ethyl]-5-methoxy-1''H''-indole || |- | 120px|class=skin-invert-image || Indolylethylfentanyl || artificial || H || colspan=2 | (CH₂)₅-4-N(COCH₂CH₃)C₆H₅ || N-[1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide || 58399-46-5 |- | 120px|class=skin-invert-image || Methylethyltryptamine (MET) | artificial | H | CH₃ | CH₂CH₃ | N-Methyl-N-ethyltryptamine | 5599-69-9 |- | 120px|class=skin-invert-image || Methylpropyltryptamine (MPT) | artificial | H | CH₃ | CH₂CH₂CH₃ | N-Methyl-N-propyltryptamine | 850032-72-3 |- | 120px|class=skin-invert-image || Methylisopropyltryptamine (MiPT) | artificial | H | CH₃ | CH(CH₃)₂ | N-Methyl-N-isopropyltryptamine | 96096-52-5 |- | 120px|class=skin-invert-image || Methylcyclopropyltryptamine (McPT) | artificial | H | CH₃ | C₃H₅ | N-Methyl-N-cyclopropyltryptamine | 1373918-63-8 |- | 120px|class=skin-invert-image || Ethylcyclopropyltryptamine (EcPT) | artificial | H | CH₂CH₃ | C₃H₅ | N-ethyl-N-cyclopropyltryptamine | |- | 120px|class=skin-invert-image || Propylcyclo{{shy}}propyltryptamine (PcPT) | artificial | H | CH₂CH₂CH₃ | C₃H₅ | N-propyl-N-cyclopropyltryptamine | |- | 120px|class=skin-invert-image || Isopropylcyclo{{shy}}propyltryptamine (iPcPT) | artificial | H | CH(CH₃)₂ | C₃H₅ | N-isopropyl-N-cyclopropyltryptamine | |- | 120px|class=skin-invert-image || Dicyclopropyltryptamine (DcPT) | artificial | H | C₃H₅ | C₃H₅ | N,N-dicyclopropyltryptamine | 1373918-62-7 |- | 120px|class=skin-invert-image || Methylbutyltryptamine (MBT) | artificial | H | CH₃ | (CH₂)₃CH₃ | N-Methyl-N-butyltryptamine | 848130-12-1 |- | 120px|class=skin-invert-image || Methyl-''sec''-butyltryptamine (MsBT) | artificial | H | CH₃ | CH(CH₃)CH₂CH₃ | N-Methyl-N-''sec''-butyltryptamine | |- | 120px|class=skin-invert-image || Methylisobutyltryptamine (MiBT) | artificial | H | CH₃ | CH₂CH(CH₃)₂ | N-Methyl-N-''iso''-butyltryptamine | |- | 120px|class=skin-invert-image || Methylcyclopropyl{{shy}}methyltryptamine (McPMT) | artificial | H | CH₃ | CH₂C₃H₅ | N-Methyl-N-(cyclopropylmethyl)tryptamine | |- | 120px|class=skin-invert-image || Deudimethyltryptamine (DMT-d₁₀; likely CYB004) | artificial | H | CH₃ | CH₃ | α,α,β,β-Tetradeutero-''N'',''N''-bis(trideuteriomethyl)tryptamine | 2742678-60-8 |- | 120px|class=skin-invert-image || SPL028 (D₂-DMT) | artificial | H | CH₃ | CH₃ | α,α-Dideutero-''N'',''N''-dimethyltryptamine | ? |- | 120px|class=skin-invert-image || Diethyltryptamine (DET) | artificial | H | CH₂CH₃ | CH₂CH₃ | ''N'',''N''-diethyltryptamine | 61-51-8 |- | 120px|class=skin-invert-image || Ethylpropyltryptamine (EPT) | artificial | H | CH₂CH₃ | CH₂CH₂CH₃ | N-Ethyl-N-propyltryptamine | 850032-68-7 |- | 120px|class=skin-invert-image || Ethylisopropyltryptamine (EiPT) | artificial | H | CH₂CH₃ | CH(CH₃)₂ | N-Ethyl-N-isopropyltryptamine | 848130-11-0 |- | 120px|class=skin-invert-image || Dipropyltryptamine (DPT) | artificial | H | CH₂CH₂CH₃ | CH₂CH₂CH₃ | ''N'',''N''-dipropyltryptamine | 61-52-9 |- | 120px|class=skin-invert-image || Propylisopropyltryptamine (PiPT) | artificial | H | CH₂CH₂CH₃ | CH(CH₃)₂ | N-Propyl-N-isopropyltryptamine | 1354632-00-0 |- | 120px|class=skin-invert-image || Diisopropyltryptamine (DiPT) | artificial | H | CH(CH₃)₂ | CH(CH₃)₂ | ''N'',''N''-diisopropyltryptamine | 14780-24-6 |- | 120px|class=skin-invert-image || Ethylbutyltryptamine (EBT) | artificial | H | CH₂CH₃ | (CH₂)₃CH₃ | N-ethyl-N-butyltryptamine | |- | 120px|class=skin-invert-image || Propylbutyltryptamine (PBT) | artificial | H | CH₂CH₂CH₃ | (CH₂)₃CH₃ | N-propyl-N-butyltryptamine | |- | 120px|class=skin-invert-image || Isopropyl-''sec''-butyltryptamine (iPsBT) | artificial | H | CH(CH₃)₂ | CH(CH₃)CH₂CH₃ | N-isopropyl-N-sec-butyltryptamine | |- | 120px|class=skin-invert-image || Dibutyltryptamine (DBT) | artificial | H | (CH₂)₃CH₃ | (CH₂)₃CH₃ | ''N'',''N''-dibutyltryptamine | 15741-77-2 |- | 120px|class=skin-invert-image || Diisobutyltryptamine (DiBT) | artificial | H | CH₂CH(CH₃)₂ | CH₂CH(CH₃)₂ | ''N'',''N''-diisobutyltryptamine | 63938-64-7 |- | 120px|class=skin-invert-image || Di-''sec''-butyltryptamine (DsBT) | artificial | H | CH(CH₃)CH₂CH₃ | CH(CH₃)CH₂CH₃ | ''N'',''N''-disecbutyltryptamine | |- | 120px|class=skin-invert-image || Diamyltryptamine (DAT) | artificial | H | (CH₂)₄CH₃ | (CH₂)₄CH₃ | ''N'',''N''-diamyltryptamine | |- | 120px|class=skin-invert-image || Dihexyltryptamine (DHT) | artificial | H | (CH₂)₅CH₃ | (CH₂)₅CH₃ | ''N'',''N''-dihexyltryptamine | |- | 120px|class=skin-invert-image || Methylallyltryptamine (MALT) | artificial | H | CH₃ | H₂C=CH-CH₂ | N-methyl-N-allyltryptamine | 1366416-29-6 |- | 120px|class=skin-invert-image || Diallyltryptamine (DALT) | artificial | H | H₂C=CH-CH₂ | H₂C=CH-CH₂ | ''N'',''N''-diallyltryptamine | 60676-77-9 |- | 120px|class=skin-invert-image || Propylallyltryptamine (PALT) | artificial | H | H₂C=CH-CH₂ | CH₂CH₂CH₃ | ''N''-propyl-''N''-allyltryptamine | 2686297-71-0 |- | 120px|class=skin-invert-image || Isopropylallyltryptamine (iPALT, ALiPT) | artificial | H | H₂C=CH-CH₂ | CH(CH₃)₂ | N-allyl-N-isopropyltryptamine | |- | 120px|class=skin-invert-image || ''N''-DEAOP-NMT | artificial | H | ? | CH₃ | ''N''-(3-diethylamino-3-oxopropyl)-''N''-methyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-''N''-DEAOP-NMT | artificial | 5-OCH₃ | ? | CH₃ | ''N''-(3-diethylamino-3-oxopropyl)-''N''-methyl-5-methoxytryptamine | |- | 120px|class=skin-invert-image || ''N''-DEAOP-NET<ref>{{cite web | title=N,N-diethyl-3-[ethyl-[2-(1H-indol-3-yl)ethyl]amino]propanamide | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/208162 | access-date=11 January 2026}}</ref> | artificial | H | ? | CH₂CH₃ | ''N''-(3-diethylamino-3-oxopropyl)-''N''-ethyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-''N''-DEAOP-NET | artificial | 5-OCH₃ | ? | CH₂CH₃ | ''N''-(3-diethylamino-3-oxopropyl)-''N''-ethyl-5-methoxytryptamine | |- | 120px|class=skin-invert-image || ''N''-Phosphonooxymethyl-DMT (''N''-POM-DMT) | artificial | H | CH₃ | CH₃ | ''N''-phosphonooxymethyl-''N'',''N''-dimethyltryptamine | ? |- | 120px|class=skin-invert-image || ''N''-Phosphonooxymethyl-5-MeO-DMT (''N''-POM-5-MeO-DMT) | artificial | 5-OCH₃ | CH₃ | CH₃ | 5-methoxy-''N''-phosphonooxymethyl-''N'',''N''-dimethyltryptamine | ? |- | 120px|class=skin-invert-image || 1-Methyl-DMT | artificial | 1-CH₃ | CH₃ | CH₃ | 1-methyl-''N'',''N''-dimethyltryptamine | 13366-47-7 |- | 120px|class=skin-invert-image || 2-Methyl-DMT | artificial | 2-CH₃ | CH₃ | CH₃ | (2-(2-methyl-1''H''-indol-3-yl)-1-methyl-ethyl)dimethylamine | 1080-95-1 |- | 120px|class=skin-invert-image || 2-Methyl-DET | artificial | 2-CH₃ | CH₂CH₃ | CH₂CH₃ | ''N'',''N''-Diethyl-2-(2-methyl-1''H''-indol-3-yl)ethan-1-amine | 26628-88-6 |- | 120px|class=skin-invert-image || 2-Methyl-DiPT | artificial | 2-CH₃ | CH(CH₃)₂ | CH(CH₃)₂ | 2-methyl-''N'',''N''-diisopropyltryptamine | |- | 120px|class=skin-invert-image || 2-Methyl-iPALT | artificial | 2-CH₃ | CH(CH₃)₂ | H₂C=CH-CH₂ | 2-methyl-''N''-isopropyl-''N''-allyltryptamine | 2915652-49-0 |- | 120px|class=skin-invert-image || 4-Amino-DMT <ref>{{cite journal | vauthors = McKay JB, Parkhurst RM, Silverstein RM, Skinner WA | title = Analogues of Psilocin and Lysergic acid diethylamide I. Chloro, Nitro, and Amino Derivatives of 3-Substituted Indoles. | journal = Canadian Journal of Chemistry | date = October 1963 | volume = 41 | issue = 10 | pages = 2585–2590 | doi = 10.1139/v63-378 | bibcode = 1963CaJCh..41.2585M }}</ref> | artificial | 4-NH₂ | CH₃ | CH₃ | 4-amino-''N'',''N''-dimethyltryptamine | 60331-61-5 |- | 120px|class=skin-invert-image || 4-Methyl-DMT | artificial | 4-CH₃ | CH₃ | CH₃ | 4,''N'',''N''-trimethyltryptamine | 28289-23-8 |- | 120px|class=skin-invert-image || 4-MeO-DMT | artificial | 4-OCH₃ | CH₃ | CH₃ | 4-methoxy-''N'',''N''-dimethyltryptamine | 3965-97-7 |- | 120px|class=skin-invert-image || 4-MeO-DET | artificial | 4-OCH₃ | CH₂CH₃ | CH₂CH₃ | 4-methoxy-''N'',''N''-diethyltryptamine | |- | 120px|class=skin-invert-image || 4-MeO-MiPT | artificial | 4-OCH₃ | CH₃ | CH(CH₃)₂ | 4-methoxy-N-methyl-N-isopropyltryptamine | 96096-53-6 |- | 120px|class=skin-invert-image || 4-MeO-DiPT | artificial | 4-OCH₃ | CH(CH₃)₂ | CH(CH₃)₂ | 4-methoxy-N,N-diisopropyltryptamine | |- | 120px|class=skin-invert-image || Deupsilocin (d₁₀-psilocin; likely CYB003) | artificial | 4-OH | CH₃ | CH₃ | 4-Hydroxy-α,α,β,β-Tetradeutero-''N'',''N''-bis(trideuteriomethyl)tryptamine | 1435934-64-7 |- | 120px|class=skin-invert-image || 4-MeS-DMT | artificial | 4-SCH₃ | CH₃ | CH₃ | 4-methylthio-''N'',''N''-dimethyltryptamine | 10455-77-3 |- | 120px|class=skin-invert-image || 4-AcO-DMT (psilacetin) | artificial | 4-OCOCH₃ | CH₃ | CH₃ | 4-acetoxy-''N'',''N''-dimethyltryptamine | 92292-84-7 |- | 120px|class=skin-invert-image || 4-PrO-DMT | artificial | 4-OCOCH₂CH₃ | CH₃ | CH₃ | 4-propionyloxy-''N'',''N''-dimethyltryptamine | 1373882-11-1 |- | 120px|class=skin-invert-image || 4-GO-DMT (RE109; FT-109) | artificial | 4-OCO(CH₂)₃COOH | CH₃ | CH₃ | 4-glutaryloxy-N,N-dimethyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-MET (metocin) | artificial | 4-OH | CH₃ | CH₂CH₃ | 4-hydroxy-N-methyl-N-ethyltryptamine | 77872-41-4 |- | 120px|class=skin-invert-image || 4-AcO-MET | artificial | 4-OCOCH₃ | CH₃ | CH₂CH₃ | 4-acetoxy-N-methyl-N-ethyltryptamine | 1445751-40-5 |- | 120px|class=skin-invert-image || 4-PrO-MET | artificial | 4-OCOCH₂CH₃ | CH₃ | CH₂CH₃ | 4-propionyloxy-N-methyl-N-ethyltryptamine | |- | 120px|class=skin-invert-image || 4-PO-MET | artificial | 4-OPO₃H₂ | CH₃ | CH₂CH₃ | 4-phosphoryloxy-N-methyl-N-ethyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-DET (ethocin) | artificial | 4-OH | CH₂CH₃ | CH₂CH₃ | 4-hydroxy-''N'',''N''-diethyltryptamine | 22204-89-3 |- | 120px|class=skin-invert-image || 4-AcO-DET | artificial | 4-OCOCH₃ | CH₂CH₃ | CH₂CH₃ | 4-acetoxy-N,N-diethyltryptamine | 1135424-15-5 |- | 120px|class=skin-invert-image || 4-PO-DET (ethocybin) | artificial | 4-OPO₃H₂ | CH₂CH₃ | CH₂CH₃ | 4-phosphoryloxy-N,N-diethyltryptamine | 60480-02-6 |- | 120px|class=skin-invert-image || 4-HO-EPT | artificial | 4-OH | CH₂CH₃ | CH₂CH₂CH₃ | 4-hydroxy-N-ethyl-N-propyltryptamine | 2595431-59-5 |- | 120px|class=skin-invert-image || 4-AcO-EPT | artificial | 4-OCOCH₃ | CH₂CH₃ | CH₂CH₂CH₃ | 4-acetoxy-N-ethyl-N-propyltryptamine | 2750249-90-0 |- | 120px|class=skin-invert-image || 4-PO-EPT | artificial | 4-OPO₃H₂ | CH₂CH₃ | CH₂CH₂CH₃ | 4-phosphoryloxy-N-ethyl-N-propyltryptamine | |- | 120px|class=skin-invert-image || 4-AcO-EiPT | artificial | 4-OCOCH₃ | CH₂CH₃ | CH(CH₃)₂ | 4-acetoxy-N-ethyl-N-isopropyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-MPT | artificial | 4-OH | CH₃ | CH₂CH₂CH₃ | 4-hydroxy-N-methyl-N-propyltryptamine | 763035-03-6 |- | 120px|class=skin-invert-image || 4-AcO-MPT | artificial | 4-OCOCH₃ | CH₃ | CH₂CH₂CH₃ | 4-acetoxy-N-methyl-N-propyltryptamine | 2173386-55-3 |- | 120px|class=skin-invert-image || 4-HO-MiPT | artificial | 4-OH | CH(CH₃)₂ | CH₃ | 4-hydroxy-''N''-isopropyl-''N''-methyltryptamine | 77872-43-6 |- | 120px|class=skin-invert-image || 4-AcO-MiPT | artificial | 4-OCOCH₃ | CH₃ | CH(CH₃)₂ | 4-acetoxy-N-methyl-N-isopropyltryptamine | 1024612-25-6 |- | 120px|class=skin-invert-image || 4-HO-MALT<ref name="pmid33860183">{{cite journal | vauthors = Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt AL | title = Investigation of the Structure-Activity Relationships of Psilocybin Analogues | journal = ACS Pharmacology & Translational Science | volume = 4 | issue = 2 | pages = 533–542 | date = April 2021 | pmid = 33860183 | pmc = 8033608 | doi = 10.1021/acsptsci.0c00176 }}</ref> | artificial | 4-OH | CH₃ | H₂C=CH-CH₂ | 4-hydroxy-N-methyl-N-allyltryptamine | |- | 120px|class=skin-invert-image || 4-AcO-MALT<ref name="pmid33614134">{{cite journal | vauthors = Pham DN, Chadeayne AR, Golen JA, Manke DR | title = Psilacetin derivatives: fumarate salts of the meth-yl-ethyl, meth-yl-allyl and diallyl variants of the psilocin prodrug | journal = Acta Crystallographica Section E | volume = 77 | issue = Pt 2 | pages = 101–106 | date = February 2021 | pmid = 33614134 | pmc = 7869532 | doi = 10.1107/S2056989021000116 | doi-access = free| bibcode = 2021AcCrE..77..101P }}</ref> | artificial | 4-OCOCH₃ | CH₃ | H₂C=CH-CH₂ | 4-acetoxy-N-Methyl-N-allyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-iPALT | artificial | 4-OH | CH(CH₃)₂ | H₂C=CH-CH₂ | 4-hydroxy-''N''-isopropyl-''N''-allyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-MBT | artificial | 4-OH | (CH₂)₃CH₃ | CH₃ | 4-hydroxy-''N''-butyl-''N''-methyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-MsBT | artificial | 4-OH | CH(CH₃)CH₂CH₃ | CH₃ | 4-hydroxy-''N''-''sec''-butyl-''N''-methyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-MtBT | artificial | 4-OH | C(CH₃)₃ | CH₃ | 4-hydroxy-''N''-''tert''-butyl-''N''-methyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-EiBT | artificial<ref>{{cite patent | url = https://patents.google.com/patent/WO2023115167A1/en?oq=WO2023115167 | country = WO | number = 2023115167| inventor = Banister S, Jorgensen W, Jinlong T | title = Compounds | assignee = Psylo Pty Ltd. | pubdate = 29 June 2023 }}</ref> | 4-OH | CH₂CH(CH₃)₂ | CH₂CH₃ | 4-hydroxy-''N''-''iso''-butyl-''N''-ethyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-McPT | artificial | 4-OH | C₃H₅ | CH₃ | 4-hydroxy-''N''-cyclopropyl-''N''-methyltryptamine | 2883663-05-4 |- | 120px|class=skin-invert-image || 4-AcO-McPT | artificial | 4-OCOCH₃ | C₃H₅ | CH₃ | 4-acetoxy-''N''-cyclopropyl-''N''-methyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-McPeT | artificial | 4-OH | C₅H₉ | CH₃ | 4-hydroxy-''N''-cyclopentyl-''N''-methyltryptamine | 77872-48-1 |- | 120px|class=skin-invert-image || 4-HO-McPMT <ref>{{cite patent | url = https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2021179091&_cid=P20-KY4AHZ-40696-1 | inventor = Kozikowski A, Shaprio G, Tueckmantel W, McCorvy J | title = 3-(2-(Aminoethyl)-indol-4-ol derivatives, methods of preparation thereof, and the use as 5-HT2 receptor modulators | country = WO | number = 2021179091 | assign1 = Bright Minds Biosciences Inc. | assign2 = The Medical College Of Wisconsin Inc. | pubdate = 16 September 2021 }}</ref> | artificial | 4-OH | CH₂C₃H₅ | CH₃ | 4-hydroxy-''N''-cyclopropylmethyl-''N''-methyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-DPT | artificial | 4-OH | CH₂CH₂CH₃ | CH₂CH₂CH₃ | 4-hydroxy-''N'',''N''-dipropyltryptamine | 63065-88-3 |- | 120px|class=skin-invert-image || 4-AcO-DPT | artificial | 4-OCOCH₃ | CH₂CH₂CH₃ | CH₂CH₂CH₃ | 4-acetoxy-N,N-dipropyltryptamine | 1445751-75-6 |- | 120px|class=skin-invert-image || 4-Methylcarbonato-DPT (4-MeCO3-DPT)<ref name="GlatfelterChadeayneManke2026">{{cite journal | last1=Glatfelter | first1=Grant C. | last2=Chadeayne | first2=Andrew R. | last3=Manke | first3=David R. | last4=Baumann | first4=Michael R. | title=Psychedelic-Like Effects of 4-Substituted N,N-Dipropyltryptamine Analogs (Abstract ID: 230619) | journal=The Journal of Pharmacology and Experimental Therapeutics | volume=393 | issue=5 | date=2026 | doi=10.1016/j.jpet.2026.104296 | article-number=104296 | url=https://linkinghub.elsevier.com/retrieve/pii/S0022356526004957 | access-date=28 May 2026}}</ref><ref name="PegoSchoffnerSammeta2025">{{cite journal | vauthors = Pego AM, Schoffner M, Sammeta VR, Naeem M, Manke DR, Chadeayne A, Glatfelter GC, Baumann MH, Concheiro-Guisán M | title = Development and validation of an analytical method for the determination of select 4-position ring-substituted tryptamines in plasma by liquid chromatography-tandem mass spectrometry | journal = J Anal Toxicol | volume = 49 | issue = 6 | pages = 376–383 | date = July 2025 | pmid = 40418247 | pmc = 13031101 | doi = 10.1093/jat/bkaf045 | url = }}</ref><ref>{{cite web | title=[3-[2-(dipropylamino)ethyl]-1H-indol-4-yl] methyl carbonate | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/163399464 | access-date=28 May 2026}}</ref> | artificial | 4-MeCO₃ | CH₂CH₂CH₃ | CH₂CH₂CH₃ | 4-methylcarbonato-''N'',''N''-dipropyltryptamine | ? |- | 120px|class=skin-invert-image || 4-HO-PiPT | artificial | 4-OH | CH₂CH₂CH₃ | CH(CH₃)₂ | 4-hydroxy-''N''-propyl-''N''-isopropyltryptamine | |- | 120px|class=skin-invert-image || 4-AcO-PiPT | artificial | 4-OCOCH₃ | CH₂CH₂CH₃ | CH(CH₃)₂ | 4-acetoxy-''N''-propyl-''N''-isopropyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-DiPT | artificial | 4-OH | CH(CH₃)₂ | CH(CH₃)₂ | 4-hydroxy-''N'',''N''-diisopropyltryptamine | 132328-45-1 |- | 120px|class=skin-invert-image || 4-AcO-DiPT | artificial | 4-OCOCH₃ | CH(CH₃)₂ | CH(CH₃)₂ | 4-acetoxy-N,N-diisopropyltryptamine | 936015-60-0 |- | 120px|class=skin-invert-image || 4-PrO-DiPT | artificial | 4-OCOCH₂CH₃ | CH(CH₃)₂ | CH(CH₃)₂ | 4-propionyloxy-N,N-diisopropyltryptamine | 1373882-13-3 |- | 120px|class=skin-invert-image || Luvesilocin (RE104; FT-104) | artificial | 4-OCO(CH₂)₃COOH | CH(CH₃)₂ | CH(CH₃)₂ | 4-glutaryloxy-N,N-diisopropyltryptamine | |- | 120px|class=skin-invert-image || 4-PO-DiPT | artificial | 4-OPO₃H₂ | CH(CH₃)₂ | CH(CH₃)₂ | 4-phosphoryloxy-N,N-diisopropyltryptamine | 1373882-09-7 |- | 120px|class=skin-invert-image || 4-HO-DALT | artificial | 4-OH | H₂C=CH-CH₂ | H₂C=CH-CH₂ | 4-hydroxy-N,N-diallyltryptamine | 2173386-70-2 |- | 120px|class=skin-invert-image || 4-AcO-DALT | artificial | 4-OCOCH₃ | H₂C=CH-CH₂ | H₂C=CH-CH₂ | 4-acetoxy-N,N-diallyltryptamine | 1445751-71-2 |- | 120px|class=skin-invert-image || 4-HO-DBT | artificial | 4-OH | (CH₂)₃CH₃ | (CH₂)₃CH₃ | 4-hydroxy-''N'',''N''-dibutyltryptamine | 63065-89-4 |- | 120px|class=skin-invert-image || 4-HO-DiBT | artificial | 4-OH | CH₂CH(CH₃)₂ | CH₂CH(CH₃)₂ | 4-hydroxy-''N'',''N''-diisobutyltryptamine | |- | 120px|class=skin-invert-image || 4-HO-DsBT | artificial | 4-OH | CH(CH₃)CH₂CH₃ | CH(CH₃)CH₂CH₃ | 4-hydroxy-''N'',''N''-disecbutyltryptamine | 127507-01-1 |- | 120px|class=skin-invert-image || 4-Fluoro-DMT | artificial | 4-F | CH₃ | CH₃ | 4-fluoro-''N'',''N''-dimethyltryptamine | 1644-64-0 |- | 120px|class=skin-invert-image || 5-MeO-DMT-d4 (α,α,β,β-tetradeutero-5-MeO-DMT) | artificial | 5-OCH₃ | CH₃ | CH₃ | α,α,β,β-Tetradeutero-5-methoxy-''N'',''N''-dimethyltryptamine | 66521-37-7 |- | 120px|class=skin-invert-image || 5-MeO-MET | artificial | 5-OCH₃ | CH₂CH₃ | CH₃ | 5-methoxy-''N''-methyl-''N''-ethyltryptamine | 16977-53-0 |- | 120px|class=skin-invert-image || 5-MeO-DET | artificial | 5-OCH₃ | CH₂CH₃ | CH₂CH₃ | 5-methoxy-''N'',''N''-diethyltryptamine | 2454-70-8 |- | 120px|class=skin-invert-image || 5-MeO-MPT | artificial | 5-OCH₃ | CH₃ | CH₂CH₂CH₃ | 5-methoxy-''N''-methyl-''N''-propyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-EPT | artificial | 5-OCH₃ | CH₂CH₃ | CH₂CH₂CH₃ | 5-methoxy-''N''-ethyl-''N''-propyltryptamine | 850032-67-6 |- | 120px|class=skin-invert-image || 5-MeO-DPT | artificial | 5-OCH₃ | CH₂CH₂CH₃ | CH₂CH₂CH₃ | 5-methoxy-''N'',''N''-dipropyltryptamine | 69496-75-9 |- | 120px|class=skin-invert-image || 5-MeO-MALT | artificial | 5-OCH₃ | H₂C=CH-CH₂ | CH₃ | 5-methoxy-''N''-Methyl-''N''-allyltryptamine | 1373918-64-9 |- | 120px|class=skin-invert-image || 5-MeO-DALT | artificial | 5-OCH₃ | H₂C=CH-CH₂ | H₂C=CH-CH₂ | 5-methoxy-''N'',''N''-diallyltryptamine | 928822-98-4 |- | 120px|class=skin-invert-image || ASR-3001 (5-MeO-iPALT) | artificial | 5-OCH₃ | H₂C=CH-CH₂ | CH₂CH(CH₃)₂ | 5-methoxy-N-allyl-N-isopropyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-MiPT | artificial | 5-OCH₃ | CH₃ | CH(CH₃)₂ | 5-methoxy-''N'',''N''-methylisopropyltryptamine | 96096-55-8 |- | 120px|class=skin-invert-image || 5,6-MeO-MiPT | artificial | 5-OCH₃, 6-OCH₃ | CH₃ | CH(CH₃)₂ | 5,6-dimethoxy-''N'',''N''-methylisopropyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-MBT | artificial | 5-OCH₃ | CH₃ | (CH₂)₃CH₃ | 5-methoxy-''N''-methyl-''N''-butyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-MsBT | artificial | 5-OCH₃ | CH₃ | CH(CH₃)CH₂CH₃ | 5-methoxy-''N''-methyl-''N''-''sec''-butyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-McPT | artificial | 5-OCH₃ | CH₃ | C₃H₅ | 5-methoxy-''N''-methyl-''N''-cyclopropyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-McBT | artificial | 5-OCH₃ | CH₃ | C₄H₇ | 5-methoxy-''N''-methyl-''N''-cyclobutyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-EiPT | artificial | 5-OCH₃ | CH₂CH₃ | CH(CH₃)₂ | 5-methoxy-N-ethyl-N-isopropyltryptamine | 850032-66-5 |- | 120px|class=skin-invert-image || 5-MeO-PiPT | artificial | 5-OCH₃ | CH₂CH₂CH₃ | CH(CH₃)₂ | 5-methoxy-''N''-propyl-''N''-isopropyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-DiPT | artificial | 5-OCH₃ | CH(CH₃)₂ | CH(CH₃)₂ | 5-methoxy-''N'',''N''-diisopropyltryptamine | 4021-34-5 |- | 120px|class=skin-invert-image || 5-MeO-DBT | artificial | 5-OCH₃ | (CH₂)₃CH₃ | (CH₂)₃CH₃ | 5-methoxy-''N'',''N''-dibutyltryptamine | 73785-42-9 |- | 120px|class=skin-invert-image || 5-MeO-DsBT | artificial | 5-OCH₃ | CH(CH₃)CH₂CH₃ | CH(CH₃)CH₂CH₃ | 5-methoxy-''N'',''N''-di-''sec''-butyltryptamine | |- | 120px|class=skin-invert-image || 5-MeS-DMT | artificial | 5-SCH₃ | CH₃ | CH₃ | 5-methylthio-''N'',''N''-dimethyltryptamine | 5102-11-4 |- | 120px|class=skin-invert-image || 5-AcO-DMT (''O''-acetylbufotenine) | artificial | 5-OCOCH₃ | CH₃ | CH₃ | 5-acetoxy-''N'',''N''-dimethyltryptamine | 16977-50-7 |- | 120px|class=skin-invert-image || 5-''t''-BuCO-DMT (''O''-pivalylbufotenine) | artificial | ? | CH₃ | CH₃ | 5-pivaloxy-''N'',''N''-dimethyltryptamine | ? |- | 120px|class=skin-invert-image || 5-AcO-MET <ref>{{cite patent | url = https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2021101926 | inventor = Stamets PE | title = Tryptamine Compositions for Enhancing Neurite Outgrowth. | country = WO | number = 2021101926 | pubdate = 2021-05-27 | assign1 = Stamets Paul Edward | postscript = . }}</ref> | artificial | 5-OCOCH₃ | CH₃ | CH₂CH₃ | 5-acetoxy-N-methyl-N-ethyltryptamine | |- | 120px|class=skin-invert-image || 5-AcO-DET | artificial | 5-OCOCH₃ | CH₂CH₃ | CH₂CH₃ | 5-acetoxy-''N'',''N''-diethyltryptamine | |- | 120px|class=skin-invert-image || 5-AcO-EPT <ref>{{cite patent | url = https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2021168082 | inventor = Kruegel AC, Sporn J | title = Specific Tryptamines for use in the Treatment of Mood Disorders. | country = WO | number = 2021168082 | pubdate = 26 August 2021 }}</ref> | artificial | 5-OCOCH₃ | CH₂CH₃ | CH₂CH₂CH₃ | 5-acetoxy-N-ethyl-N-propyltryptamine | |- | 120px|class=skin-invert-image || 5-AcO-DPT | artificial | 5-OCOCH₃ | CH₂CH₂CH₃ | CH₂CH₂CH₃ | 5-acetoxy-''N'',''N''-dipropyltryptamine | |- | 120px|class=skin-invert-image || 5-AcO-MiPT | artificial | 5-OCOCH₃ | CH₃ | CH(CH₃)₂ | 5-acetoxy-N-methyl-N-isopropyltryptamine | |- | 120px|class=skin-invert-image || 5-AcO-DiPT | artificial | 5-OCOCH₃ | CH(CH₃)₂ | CH(CH₃)₂ | 5-acetoxy-''N'',''N''-diisopropyltryptamine | |- | 120px|class=skin-invert-image || 5-Ethoxy-DMT || artificial || 5-OCH₂CH₃ || CH₃ || CH₃ || 5-ethoxy-''N'',''N''-dimethyltryptamine || 855245-09-9 |- | 120px|class=skin-invert-image || 5-Ethoxy-MET || artificial || 5-OCH₂CH₃ || CH₃ || CH₂CH₃ || 5-ethoxy-N-methyl-N-ethyltryptamine || |- | 120px|class=skin-invert-image || 5-Ethoxy-DET || artificial || 5-OCH₂CH₃ || CH₂CH₃ || CH₂CH₃ || 5-ethoxy-N,N-diethyltryptamine || |- | 120px|class=skin-invert-image || 5-Ethoxy-MPT || artificial || 5-OCH₂CH₃ || CH₃ || CH₂CH₂CH₃ || 5-ethoxy-N-methyl-N-propyltryptamine || |- | 120px|class=skin-invert-image || 5-Ethoxy-EPT || artificial || 5-OCH₂CH₃ || CH₂CH₃ || CH₂CH₂CH₃ || 5-ethoxy-N-ethyl-N-propyltryptamine || |- | 120px|class=skin-invert-image || 5-Ethoxy-DPT || artificial || 5-OCH₂CH₃ || CH₂CH₂CH₃ || CH₂CH₃ || 5-ethoxy-N,N-dipropyltryptamine || |- | 120px|class=skin-invert-image || 5-Ethoxy-MiPT || artificial || 5-OCH₂CH₃ || CH₃ || CH(CH₃)₂ || 5-ethoxy-N-methyl-N-isopropyltryptamine || |- | 120px|class=skin-invert-image || 5-Ethoxy-EiPT || artificial || 5-OCH₂CH₃ || CH₂CH₃ || CH(CH₃)₂ || 5-ethoxy-N-ethyl-N-isopropyltryptamine || |- | 120px|class=skin-invert-image || 5-Ethoxy-DiPT || artificial || 5-OCH₂CH₃ || CH(CH₃)₂ || CH(CH₃)₂ || 5-ethoxy-N,N-diisopropyltryptamine || |- | 120px|class=skin-invert-image || 5-Ethoxy-DALT || artificial || 5-OCH₂CH₃ || H₂C=CH-CH₂ || H₂C=CH-CH₂ || 5-ethoxy-N,N-diallyltryptamine || |- | 120px|class=skin-invert-image || 5-BnO-DMT | artificial | 5-OCH₂C₆H₅ | CH₃ | CH₃ | 5-benzyloxy-''N'',''N''-dimethyltryptamine | 101832-88-6 |- | 120px|class=skin-invert-image || 5-HO-MET | artificial | 5-OH | CH₃ | CH₂CH₃ | 5-hydroxy-''N''-methyl-''N''-ethyltryptamine | 1443666-13-4 |- | 120px|class=skin-invert-image || 5-HO-DET | artificial | 5-OH | CH₂CH₃ | CH₂CH₃ | 5-hydroxy-''N'',''N''-diethyltryptamine | 14009-42-8 |- | 120px|class=skin-invert-image || 5-HO-DPT | artificial | 5-OH | CH₂CH₂CH₃ | CH₂CH₂CH₃ | 5-hydroxy-''N'',''N''-dipropyltryptamine | 36288-75-2 |- | 120px|class=skin-invert-image || 5-HO-MiPT | artificial | 5-OH | CH₃ | CH(CH₃)₂ | 5-hydroxy-N-methyl-N-isopropyltryptamine | |- | 120px|class=skin-invert-image || 5-HO-DiPT | artificial | 5-OH | CH(CH₃)₂ | CH(CH₃)₂ | 5-hydroxy-''N'',''N''-diisopropyltryptamine | 36288-76-3 |- | 120px|class=skin-invert-image || 5-Methyl-DMT (5,''N'',''N''-TMT) || artificial || 5-CH₃ || CH₃ || CH₃ || 5,''N'',''N''-trimethyltryptamine || 22120-39-4 |- | 120px|class=skin-invert-image || 5-Ethyl-DMT || artificial || 5-CH₂CH₃ || CH₃ || CH₃ || 5-ethyl-''N'',''N''-dimethyltryptamine || 171783-25-8 |- | 120px|class=skin-invert-image || 5-Isopropyl-DMT || artificial || 5-CH(CH₃)₂ || CH₃ || CH₃ || 5-isopropyl-''N'',''N''-dimethyltryptamine || 156281-04-8 |- | 120px|class=skin-invert-image || 5-(''t''-Butyl)-DMT <ref name="pmid9986723">{{cite journal | vauthors = Xu YC, Schaus JM, Walker C, Krushinski J, Adham N, Zgombick JM, Liang SX, Kohlman DT, Audia JE | title = N-Methyl-5-tert-butyltryptamine: A novel, highly potent 5-HT1D receptor agonist | journal = Journal of Medicinal Chemistry | volume = 42 | issue = 3 | pages = 526–31 | date = February 1999 | pmid = 9986723 | doi = 10.1021/jm9805945 }}</ref> || artificial || 5-C(CH₃)₃ || CH₃ || CH₃ || 5-(''tert''-butyl)-''N'',''N''-dimethyltryptamine || |- | 120px|class=skin-invert-image || 5-Fluoro-DMT || artificial || 5-F || CH₃ || CH₃ || 5-fluoro-''N'',''N''-dimethyltryptamine || 22120-36-1 |- | 120px|class=skin-invert-image || Bretisilocin (5-fluoro-MET; GM-2505) || artificial || 5-F || CH₃ || CH₂CH₃ || 5-fluoro-N-methyl-N-ethyltryptamine || 2698331-35-8 |- | 120px|class=skin-invert-image || 5-Fluoro-DET || artificial || 5-F || CH₂CH₃ || CH₂CH₃ || 5-fluoro-''N'',''N''-diethyltryptamine || |- | 120px|class=skin-invert-image || 5-Fluoro-EPT || artificial || 5-F || CH₂CH₃ || CH₂CH₂CH₃ || 5-fluoro-N-ethyl-N-propyltryptamine || |- | 120px|class=skin-invert-image || 5-Fluoro-DPT || artificial || 5-F || CH₂CH₂CH₃ || CH₂CH₂CH₃ || 5-fluoro-''N'',''N''-dipropyltryptamine || |- | 120px|class=skin-invert-image || 5-Fluoro-PiPT || artificial || 5-F || CH₂CH₂CH₃ || CH(CH₃)₂ || 5-fluoro-''N''-propyl-''N''-isopropyltryptamine || |- | 120px|class=skin-invert-image || 5-Fluoro-PcBT || artificial || 5-F || CH₂CH₂CH₃ || CH(CH₂)₃ || 5-fluoro-''N''-propyl-''N''-cyclobutyltryptamine || |- | 120px|class=skin-invert-image || 5-Fluoro-iPcBT || artificial || 5-F || CH(CH₃)₂ || CH(CH₂)₃ || 5-fluoro-''N''-isopropyl-''N''-cyclobutyltryptamine || |- | 120px|class=skin-invert-image || 5-Fluoro-DiPT || artificial || 5-F || CH(CH₃)₂ || CH(CH₃)₂ || 5-fluoro-''N'',''N''-diisoproptryptamine || |- | 120px|class=skin-invert-image || 5-Fluoro-sBALT || artificial || 5-F || CH(CH₃)CH₂CH₃ || CH₂CH=CH₂ || 5-fluoro-N-''sec''-butyl-N-allyltryptamine || |- | 120px|class=skin-invert-image || 5-Fluoro-M1MALT || artificial || 5-F || CH₃ || CH(CH₃)CH=CH₂ || 5-fluoro-N-methyl-N-(1-methylallyl)tryptamine || |- | 120px|class=skin-invert-image || 5-Chloro-DMT || artificial || 5-Cl || CH₃ || CH₃ || 5-chloro-''N'',''N''-dimethyltryptamine || 22120-32-7 |- | 120px|class=skin-invert-image || 5-Iodo-DMT || artificial || 5-I || CH₃ || CH₃ || 5-iodo-''N'',''N''-dimethyltryptamine || 22120-38-3 |- | 120px|class=skin-invert-image || 5-TFM-DMT || artificial || 5-CF₃ || CH₃ || CH₃ || 5-(trifluoromethyl)-''N'',''N''-dimethyltryptamine || 2418713-32-1 |- | 120px|class=skin-invert-image || 5-TFMO-DMT<ref>{{cite patent | url = https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022235927 | inventor = Kruegel AC | title = Novel Tryptamines and Methods of Treating Mood Disorders | country = WO | number = 2022235927 | assign1 = Gilgamesh Pharmaceuticals, Inc. | pubdate = 10 November 2022 }}</ref> || artificial || 5-OCF₃ || CH₃ || CH₃ || 5-(trifluoromethoxy)-''N'',''N''-dimethyltryptamine || |- | 120px|class=skin-invert-image || 5-Nitro-DMT<ref>{{cite journal | vauthors = Shaw E, Woolley DW | title = The synthesis of nitro-and aminoindoles analogous to serotonin. | journal = Journal of the American Chemical Society | date = April 1953 | volume = 75 | issue = 8 | pages = 1877–1881 | doi = 10.1021/ja01104a029 | bibcode = 1953JAChS..75.1877S }}</ref> || artificial || 5-NO₂ || CH₃ || CH₃ || 5-nitro-''N'',''N''-dimethyltryptamine || 69937-13-9 |- | 120px|class=skin-invert-image || 5-CN-DMT || artificial || 5-C≡N || CH₃ || CH₃ || 5-cyano-''N'',''N''-dimethyltryptamine || 17380-42-6 |- | 120px|class=skin-invert-image || 5-CN-DPT || artificial || 5-C≡N || CH₂CH₂CH₃ || CH₂CH₂CH₃ || 5-cyano-''N'',''N''-dipropyltryptamine || 74885-19-1 |- | 120px|class=skin-invert-image || Almotriptan | artificial | 5-(CH₂SO₂N(CH₂)₄) | CH₃ | CH₃ | ''N'',''N''-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1''H''-indol-3-yl]-ethanamine | 154323-57-6 |- | 120px|class=skin-invert-image || Rizatriptan | artificial | 5-(CH₂(N₃(CH)₂)) | CH₃ | CH₃ | ''N'',''N''-dimethyl-2-[5-(1''H''-1,2,4-triazol-1-ylmethyl)-1''H''-indol-3-yl]ethanamine | 145202-66-0 |- | 120px|class=skin-invert-image || Sumatriptan | artificial | 5-(CH₂SO₂NHCH₃) | CH₃ | CH₃ | 1-[3-(2-Dimethylaminoethyl)-1''H''-indol-5-yl]-''N''-methyl-methanesulfonamide | 103628-46-2 |- | 120px|class=skin-invert-image || Zolmitriptan | artificial | 5-(CHNHC=OOCH₂) | CH₃ | CH₃ | 5-( 4-(''S'')-1,3-oxazolidin-2-one)-''N'',''N''-dimethyltryptamine | 139264-17-8 |- | 120px|class=skin-invert-image || 6-Fluoro-DMT || artificial || 6-F || CH₃ || CH₃ || 6-fluoro-''N'',''N''-dimethyltryptamine || 1511-31-5 |- | 120px|class=skin-invert-image || 6-Fluoro-DET<ref name="Rabin_2002">{{cite journal | vauthors = Rabin RA, Regina M, Doat M, Winter JC | title = 5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens | journal = Pharmacology, Biochemistry, and Behavior | volume = 72 | issue = 1–2 | pages = 29–37 | date = May 2002 | pmid = 11900766 | doi = 10.1016/s0091-3057(01)00720-1 | s2cid = 6480715 }}</ref> || artificial || 6-F || CH₂CH₃ || CH₂CH₃ || 6-fluoro-''N'',''N''-diethyltryptamine || 2836-69-3 |- | 120px|class=skin-invert-image || 6-Chloro-DMT || artificial || 6-Cl || CH₃ || CH₃ || 6-chloro-''N'',''N''-dimethyltryptamine || 25390-72-1 |- | 120px|class=skin-invert-image || 6-Methyl-DMT || artificial || 6-CH₃ || CH₃ || CH₃ || 6,''N'',''N''-trimethyltryptamine || |- | 120px|class=skin-invert-image || 6-Hydroxy-DMT || artificial || 6-OH || CH₃ || CH₃ || 6-hydroxy-''N'',''N''-dimethyltryptamine || 1476-33-1 |- | 120px|class=skin-invert-image || 6-Hydroxy-DET || artificial || 6-OH || CH₃ || CH₃ || 6-hydroxy-''N'',''N''-diethyltryptamine || 1476-59-1 |- | 120px|class=skin-invert-image || 6-Methoxy-DMT || artificial || 6-OCH₃ || CH₃ || CH₃ || 6-methoxy-''N'',''N''-dimethyltryptamine || 2426-88-2 |- | 120px|class=skin-invert-image || 6-TFMO-DMT (6-trifluoromethoxy-DMT)<ref>{{cite web | title=N,N-dimethyl-2-[6-(trifluoromethoxy)-1H-indol-3-yl]ethanamine | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/172291242 | access-date=13 May 2026}}</ref><ref name="ChenLiYu2023b">{{citation | vauthors = Chen X, Li J, Yu L, Dhananjaya D, Maule F, Cook S, Chang L, Gallant J, Press D, Bains JS, Raithatha S, Hagel S, Facchini P | title=Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery | date=10 March 2023 | doi=10.21203/rs.3.rs-2667175/v1 | doi-access=free | url=https://www.researchsquare.com/article/rs-2667175/latest.pdf | access-date=17 March 2025 | page=}}</ref><ref name="ChenLiYu2023a">{{cite journal | vauthors = Chen X, Li J, Yu L, Maule F, Chang L, Gallant JA, Press DJ, Raithatha SA, Hagel JM, Facchini PJ | title = A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines | journal = The Journal of Biological Chemistry | volume = 299 | issue = 10 | article-number = 105231 | date = October 2023 | pmid = 37690691 | pmc = 10570959 | doi = 10.1016/j.jbc.2023.105231 | doi-access = free }}</ref> || artificial || 6-OCF₃ || CH₃ || CH₃ || 6-trifluoromethoxy-''N'',''N''-dimethyltryptamine || |- | 120px|class=skin-invert-image || 7-Methyl-DMT || artificial || 7-CH₃ || CH₃ || CH₃ || 7,''N'',''N''-trimethyltryptamine || 65882-39-5 |- | 120px|class=skin-invert-image || 7-Ethyl-DMT || artificial || 7-CH₂CH₃ || CH₃ || CH₃ || 7-ethyl-''N'',''N''-dimethyltryptamine || |- | 120px|class=skin-invert-image || 7-Chloro-DMT || artificial || 7-Cl || CH₃ || CH₃ || 7-chloro-''N'',''N''-dimethyltryptamine || |- | 120px|class=skin-invert-image || 7-Bromo-DMT<ref name="pmid6779006">{{cite journal | vauthors = Glennon RA, Schubert E, Jacyno JM, Rosecrans JA | title = Studies on several 7-substituted N,N-dimethyltryptamines | journal = Journal of Medicinal Chemistry | volume = 23 | issue = 11 | pages = 1222–6 | date = November 1980 | pmid = 6779006 | doi = 10.1021/jm00185a014 }}</ref> || artificial || 7-Br || CH₃ || CH₃ || 7-bromo-''N'',''N''-dimethyltryptamine || 74798-68-8 |- | 120px|class=skin-invert-image || 7-Hydroxy-DMT || artificial || 7-OH || CH₃ || CH₃ || 7-hydroxy-''N'',''N''-dimethyltryptamine || 7578-26-9 |- | 120px|class=skin-invert-image || 7-Methoxy-DMT || artificial || 7-OCH₃ || CH₃ || CH₃ || 7-methoxy-''N'',''N''-dimethyltryptamine || |- | 120px|class=skin-invert-image || 7-Methoxy-MiPT || artificial || 7-OCH₃ || CH₃ || CH(CH₃)₂|| 7-methoxy-''N''-methyl-''N''-isopropyltryptamine || |- | 120px|class=skin-invert-image || 1-Methylpsilocin | artificial | 1-CH₃, 4-OH | CH₃ | CH₃ | 1-Methyl-3-[2-(''N'',''N''-dimethylamino)ethyl]-4-hydroxyindole | 1465-16-3 |- | 120px|class=skin-invert-image || 1-Ethylpsilocin <ref>[https://patents.google.com/patent/WO2021179091A1/en Kozikowski A, et al. 3-(2-(aminoethyl)-indol-4-ol derivatives, methods of preparation thereof, and the use as 5-ht2 receptor modulators. Patent WO 2021/179091]</ref> | artificial | 1-CH₂CH₃, 4-OH | CH₃ | CH₃ | 1-Ethyl-3-[2-(''N'',''N''-dimethylamino)ethyl]-4-hydroxyindole | 1640-02-4 |- | 120px|class=skin-invert-image || 1-Methyl-5-MeO-DiPT | artificial | 1-CH₃, 5-OCH₃ | CH(CH₃)₂ | CH(CH₃)₂ | 1-methyl-5-methoxy-''N'',''N''-diisopropyltryptamine | 1373882-10-0 |- | 100px|class=skin-invert-image || 1-Acetyl-DMT (1A-DMT; DMT AР-1)<ref>{{cite web | title=1-[3-[2-(Dimethylamino)ethyl]-1H-indol-1-yl]ethanone | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/85809048 | access-date=30 May 2026}}</ref><ref name="Kargbo2023">{{cite journal | last=Kargbo | first=Robert B. | title=Orally Active Forms of DMT, 5-MeO-DMT, and Long-Acting MDMA for the Treatment of Neuropsychiatric Disorders | journal=ACS Medicinal Chemistry Letters | volume=14 | issue=4 | date=13 April 2023 | issn=1948-5875 | pmid=37077395 | pmc=10108390 | doi=10.1021/acsmedchemlett.3c00077 | pages=367–368 | url=https://pubs.acs.org/doi/10.1021/acsmedchemlett.3c00077}}</ref><ref name="WO2023283364">{{cite web | title=N,n-dimethyltryptamine and related psychedlics and uses thereof | website=Google Patents | date=7 July 2022 | url=https://patents.google.com/patent/WO2023283364 | access-date=29 May 2026}}</ref> | artificial | 1-COCH₃ | CH₃ | CH₃ | 1-acetyl-''N'',''N''-dimethyltryptamine | 39998-62-4 |- | 100px|class=skin-invert-image || 1-Benzoyl-DMT (1Bz-DMT) | artificial | 1-COC₆H₅ | CH₃ | CH₃ | 1-benzoyl-''N'',''N''-dimethyltryptamine | 481661-45-4 |- | 100px|class=skin-invert-image || NBoc-DMT (NB-DMT) | artificial | 1-OCOC(CH₃)₃ | CH₃ | CH₃ | 1-(''t''-butoxycarbonyl)-''N'',''N''-dimethyltryptamine | 2210243-51-7 |- | 100px|class=skin-invert-image || 1-Acetyl-5-MeO-DMT (1A-5-MeO-DMT)<ref>{{cite web | title=1-[3-[2-(Dimethylamino)ethyl]-5-methoxy-1H-indol-1-yl]ethanone | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/85809049 | access-date=30 May 2026}}</ref><ref name="Kargbo2023" /><ref name="WO2023283364" /> | artificial | 1-COCH₃, 5-OCH₃ | CH₃ | CH₃ | 1-acetyl-5-methoxy-''N'',''N''-dimethyltryptamine | 39998-63-5 |- | 100px|class=skin-invert-image || NB-5-MeO-DMT<ref>{{cite web | title=Tert-butyl 3-[2-(dimethylamino)ethyl]-5-methoxyindole-1-carboxylate | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/166467630 | access-date=11 May 2026}}</ref> | artificial | 1-OCOC(CH₃)₃, 5-OCH₃ | CH₃ | CH₃ | 1-(''t''-butoxycarbonyl)-5-methoxy-''N'',''N''-dimethyltryptamine | |- | 120px|class=skin-invert-image || NB-5-MeO-MiPT | artificial | 1-OCOC(CH₃)₃, 5-OCH₃ | CH₃ | CH(CH₃)₂ | 1-(''t''-butoxycarbonyl)-5-methoxy-''N''-methyl-''N''-isopropyltryptamine | |- | 120px|class=skin-invert-image || NB-5-MeO-DALT | artificial | 1-OCOC(CH₃)₃, 5-OCH₃ | H₂C=CH-CH₂ | H₂C=CH-CH₂ | 1-(''t''-butoxycarbonyl)-5-methoxy-''N'',''N''-diallyltryptamine | |- | 120px|class=skin-invert-image || 7-Methylpsilocin (see BMB-A39a)<ref name="WO2022246554">{{cite web | title=Heterocyclic compounds and methods of preparation thereof | website=Google Patents | date=25 May 2022 | url=https://patents.google.com/patent/WO2022246554A1/en | access-date=2 April 2026}}</ref><ref name="PubChem">{{cite web | title=3-[2-(Dimethylamino)ethyl]-7-methyl-1H-indol-4-ol | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/166138173 | access-date=2 April 2026}}</ref> || artificial || 4-OH,7-Me || CH₃ || CH₃ || 4-hydroxy-7-methyl-''N'',''N''-dimethyltryptamine || 2770305-95-6 |- | 120px|class=skin-invert-image || 7-Methylpsilocybin (see BMB-201)<ref>{{cite web | title=[3-[2-(dimethylamino)ethyl]-7-methyl-1H-indol-4-yl] dihydrogen phosphate | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/162744827 | access-date=2 April 2026}}</ref><ref name="WO2022246554" /> || artificial || 4-PO,7-Me || CH₃ || CH₃ || 4-phosphoryloxy-7-methyl-''N'',''N''-dimethyltryptamine || ? |- | 120px|class=skin-invert-image || 6-Fluoropsilocin || artificial || 4-OH,6-F || CH₃ || CH₃ || 4-hydroxy-6-fluoro-N,N-dimethyltryptamine || 312314-12-8 |- | 120px|class=skin-invert-image || 6-Fluoro-7-methylpsilocin <ref>Sabnis RW. Novel Heterocyclic Compounds as 5‑HT2C Agonists for Treating Depression, Drug Addiction, Alcoholism, PTSD and Neuropathic Pain. ''ACS Med Chem Lett''. 2025 Jul 9;16(8):1488-1489. {{doi|10.1021/acsmedchemlett.5c00400}} {{pmid|40832508}}</ref> || artificial || 4-OH,6-F,7-Me || CH₃ || CH₃ || 4-hydroxy-6-fluoro-7-methyl-N,N-dimethyltryptamine || 2873459-44-8 |- | 120px|class=skin-invert-image || 6-Fluoro-5-MeO-DMT || artificial || 5-OCH₃,6-F || CH₃ || CH₃ || 5-methoxy-6-fluoro-N,N-dimethyltryptamine || |- | 120px|class=skin-invert-image || 5,6-Difluoro-EPT || artificial || 5-F, 6-F || CH₂CH₃ || CH₂CH₂CH₃ || 5,6-difluoro-N-ethyl-N-propyltryptamine || |- | 120px|class=skin-invert-image || 5-MeO-2-TMT | artificial | 2-CH₃, 5-OCH₃ | CH₃ | CH₃ | 2-(5-methoxy-2-methyl-H-indol-3-yl)-N,N-dimethylethanamine | 67292-68-6 |- | 120px|class=skin-invert-image || 5-MeO-4-TMT | artificial | 4-CH₃, 5-OCH₃ | CH₃ | CH₃ | 5-Methoxy-4,''N'',''N''-trimethyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-6-TMT ('''P-42''') | artificial | 5-OCH₃, 6-CH₃ | CH₃ | CH₃ | 5-Methoxy-6,''N'',''N''-trimethyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-7-TMT ('''P-51''') | artificial | 5-OCH₃, 7-CH₃ | CH₃ | CH₃ | 5-Methoxy-7,''N'',''N''-trimethyltryptamine | 61018-77-7 |- | 120px|class=skin-invert-image || 4-HO-5-MeO-DMT (psilomethoxin) | artificial | 4-OH, 5-OCH₃ | CH₃ | CH₃ | 4-Hydroxy-5-methoxy-''N'',''N''-dimethyltryptamine | 2433-31-0 |- | 120px|class=skin-invert-image || 5-Methylpsilocin ('''P-10''') | artificial | 4-HO, 5-CH₃ | CH₃ | CH₃ | 4-Hydroxy-5-methyl-''N'',''N''-dimethyltryptamine | |- | 120px|class=skin-invert-image || 5-Methylpsilocybin (5-Me-4-PO-DMT) | artificial | 4-PO, 5-CH₃ | CH₃ | CH₃ | 4-Phosphoryloxy-5-methyl-''N'',''N''-dimethyltryptamine | ? |- | 120px|class=skin-invert-image || 4-PO-5-MeO-DMT (5-methoxypsilocybin) | artificial | 4-PO, 5-OCH₃ | CH₃ | CH₃ | 4-Phosphoryloxy-5-methoxy-''N'',''N''-dimethyltryptamine | ? |- | 120px|class=skin-invert-image || 4-F-5-MeO-DMT | artificial | 4-F, 5-OCH₃ | CH₃ | CH₃ | 4-Fluoro-5-Methoxy-''N'',''N''-dimethyltryptamine | 312314-18-4 |- | 120px|class=skin-invert-image || 5-Me-4-HO-MiPT ('''P-66''') | artificial | 4-HO, 5-CH₃ | CH₃ | CH(CH₃)₂ | 4-Hydroxy-5-Methyl-''N''-methyl-''N''-isopropyltryptamine | |- | 120px|class=skin-invert-image || 7-Me-4-HO-DPT ('''P-89''') | artificial | 4-HO, 7-CH₃ | CH₂CH₂CH₃ | CH₂CH₂CH₃ | 4-Hydroxy-7-Methyl-''N'',''N''-dipropyltryptamine | |- | 120px|class=skin-invert-image || 5-MeO-7-F-MET | artificial | 5-OCH₃, 7-F | CH₃ | CH₂CH₃ | 5-Methoxy-7-Fluoro-''N''-methyl-''N''-ethyltryptamine | |- | 120px|class=skin-invert-image || HBL20017 (4-F-5-MeS-DMT) | artificial | 4-F, 5-SCH₃ | CH₃ | CH₃ | 4-Fluoro-5-methylthio-''N'',''N''-dimethyltryptamine | ? |- | 120px|class=skin-invert-image || HBL20016 (5-MeS-6-F-DMT) | artificial | 5-SCH₃, 6-F | CH₃ | CH₃ | 5-Methylthio-6-fluoro-''N'',''N''-dimethyltryptamine | ? |- | 120px|class=skin-invert-image || EMDT (2-ethyl-5-MeO-DMT) | artificial | 2-CH₂CH₃, 5-OCH₃ | CH₃ | CH₃ | 2-(2-ethyl-5-methoxy-1H-indol-3-yl)-''N'',''N''-dimethylethanamine | 263744-72-5 |- | 120px|class=skin-invert-image || ST-1936 (2-methyl-5-chloro-DMT) | artificial | 2-CH₃, 5-Cl | CH₃ | CH₃ | 2-(2-methyl-5-chloro-1H-indol-3-yl)-''N'',''N''-dimethylethanamine | 1210-81-7 |- | 120px|class=skin-invert-image || Benanserin (benzyl antiserotonin; BAS; MC-4788; Sq-4788) | artificial | 1-CH₂C₆H₅, 2-CH₃, 5-OCH₃ | H | H | 2-(1-benzyl-5-methoxy-2-methylindol-3-yl)ethanamine | 441-91-8 |- | 120px|class=skin-invert-image || O-4310 (1-isopropyl-6-fluoropsilocin) | artificial | 1-CH(CH₃)₂, 4-OH, 6-F | CH₃ | CH₃ | 3-[2-(dimethylamino)ethyl]-6-fluoro-1-isopropyl-1H-indol-4-ol | 885671-63-6 |- | 130px|class=skin-invert-image || Indorenate (TR-3369) | artificial | 5-OCH₃, β-COOCH₃ | H | H | β-Methoxycarbonyl-5-methoxytryptamine | 73758-06-2 |- | 120px|class=skin-invert-image || CP-132,484 (4,5-DHP-1-Me-T) | artificial | 1-methyl-4,5-(OCH₂CH₂CH₂) | H | H | 1-(2-aminoethyl)-3-methyl-8,9-dihydropyrano(3,2-e)indole | 143508-76-3 |- | 120px|class=skin-invert-image || 4,5-DHP-DMT | artificial | 4,5-(OCH₂CH₂CH₂) | CH₃ | CH₃ | 1-(2-dimethylaminoethyl)-8,9-dihydropyrano[3,2-''e'']indole | 135360-97-3 |- | 120px|class=skin-invert-image || 4,5-DHF-DMT ('''P-3''') | artificial<ref>{{cite patent | url = https://patents.google.com/patent/WO2023115166A1/en?oq=WO2023115166 | country = WO | number = 2023115166 | inventor = Banister S, Jorgensen W, Jinlong T | assignee = Psylo Pty Ltd. | pubdate = 29 June 2023| title = Compounds }}</ref> | 4,5-(CH₂CH₂O) | CH₃ | CH₃ | 2-(3,6-dihydro-2H-furo[2,3-e]indol-8-yl)-N,N-dimethylethan-1-amine | |- | 120px|class=skin-invert-image || 4,5-Methylbenzoxazole-DMT ('''P-131''') | artificial | 4,5-(OC(CH₃)=N) | CH₃ | CH₃ | N,N-dimethyl-2-(2-methyl-6H-[1,3]oxazolo[4,5-e]indol-8-yl)ethan-1-amine | |- | 120px|class=skin-invert-image || 4,5-MDO-DMT | artificial | 4,5-(OCH₂O) | CH₃ | CH₃ | 2-(2''H'',6''H''-[1,3]Dioxolo[4,5-''e'']indol-8-yl)-''N'',''N''-dimethylethan-1-amine | 81249-30-1 |- | 120px|class=skin-invert-image || 4,5-MDO-DiPT | artificial | 4,5-(OCH₂O) | CH(CH₃)₂ | CH(CH₃)₂ | ''N''-[2-(2''H'',6''H''-[1,3]Dioxolo[4,5-''e'']indol-8-yl)ethyl]-''N''-(propan-2-yl)propan-2-amine | 82173-82-8 |- | 120px|class=skin-invert-image || 5,6-FUR-DMT ('''P-4''') | artificial | 5,6-(CH=CHO) | CH₃ | CH₃ | 2-(7H-furo[3,2-f]indol-5-yl)-N,N-dimethylethan-1-amine | |- | 120px|class=skin-invert-image || 5,6-MDO-DMT | artificial | 5,6-(OCH₂O) | CH₃ | CH₃ | 2-(2''H'',5''H''-[1,3]Dioxolo[4,5-''f'']indol-7-yl)-''N'',''N''-dimethylethan-1-amine | |- | 120px|class=skin-invert-image || 5,6-MDO-MiPT | artificial | 5,6-(OCH₂O) | CH₃ | CH(CH₃)₂ | ''N''-[2-(2''H'',5''H''-[1,3]Dioxolo[4,5-''f'']indol-7-yl)ethyl]-''N''-methylpropan-2-amine | |- | 120px|class=skin-invert-image || 5,6-MDO-DiPT | artificial | 5,6-(OCH₂O) | CH(CH₃)₂ | CH(CH₃)₂ | ''N''-[2-(2''H'',5''H''-[1,3]Dioxolo[4,5-''f'']indol-7-yl)ethyl]-''N''-(propan-2-yl)propan-2-amine | |- |- class="sortbottom" |}

===List of substituted α-alkyltryptamines=== '''α-Alkyltryptamines''' are a group of substituted tryptamines which possess an alkyl group, such as a methyl or ethyl group, attached at the alpha carbon, and in most cases no substitution on the amine nitrogen.<ref name="RiesMiller2009">{{cite book| vauthors = Ries RK, Miller SC, Fiellin DA |title=Principles of Addiction Medicine|url=https://books.google.com/books?id=j6GGBud8DXcC&pg=PT245|year=2009|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-7477-2|pages=216–218}}</ref><ref name="Laing2003">{{cite book| vauthors = Laing RR |title=Hallucinogens: A Forensic Drug Handbook|url=https://books.google.com/books?id=l1DrqgobbcwC&pg=PA102|year=2003|publisher=Academic Press|isbn=978-0-12-433951-4|pages=102–}}</ref><ref name="LemkeWilliams2012">{{cite book| vauthors = Lemke TL, Williams DA |title=Foye's Principles of Medicinal Chemistry|url=https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA641|date=24 January 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-60913-345-0|pages=641–}}</ref> α-Alkylation of tryptamine makes it much more metabolically stable and resistant to degradation by monoamine oxidase, resulting in increased potency and greatly lengthened half-life.<ref name="LemkeWilliams2012" /> This is analogous to α-methylation of phenethylamine into amphetamine.<ref name="LemkeWilliams2012" />

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors,<ref name="pmid17223101">{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = European Journal of Pharmacology | volume = 559 | issue = 2–3 | pages = 132–7 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 }}</ref><ref name="pmid25193229">{{cite journal | vauthors = Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB | title = Alpha-ethyltryptamines as dual dopamine-serotonin releasers | journal = Bioorganic & Medicinal Chemistry Letters | volume = 24 | issue = 19 | pages = 4754–4758 | date = October 2014 | pmid = 25193229 | pmc = 4211607 | doi = 10.1016/j.bmcl.2014.07.062 }}</ref><ref name="pmid18057721">{{cite journal | vauthors = Nonaka R, Nagai F, Ogata A, Satoh K | title = In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes | journal = Biological & Pharmaceutical Bulletin | volume = 30 | issue = 12 | pages = 2328–33 | date = December 2007 | pmid = 18057721 | doi = 10.1248/bpb.30.2328 | doi-access = free }}</ref><ref name="pmid1107123">{{cite journal | vauthors = Feldman JM, Chapman B | title = Monoamine oxidase inhibitors: nature of their interaction with rabbit pancreatic islets to alter insluin secretion | journal = Diabetologia | volume = 11 | issue = 6 | pages = 487–94 | date = December 1975 | pmid = 1107123 | doi = 10.1007/bf01222097 | doi-access = free }}</ref> and produce psychostimulant, entactogen, and/or psychedelic effects.<ref name="RiesMiller2009" /><ref name="Laing2003" /><ref name="LemkeWilliams2012" /> The most well-known of these agents are α-methyltryptamine (AMT) and α-ethyltryptamine (AET), both of which were used clinically as antidepressants for a brief period of time in the past and are abused as recreational drugs.<ref name="Laing2003" /><ref name="LemkeWilliams2012" /> In accordance with its action as a dual releasing agent of serotonin and dopamine, AET has been found to produce serotonergic neurotoxicity similarly to amphetamines like MDMA and PCA, and the same is also likely to hold true for other serotonin and dopamine-releasing α-alkyltryptamines such as AMT, 5-MeO-AMT, and various others.<ref name="pmid1722753">{{cite journal | vauthors = Huang XM, Johnson MP, Nichols DE | title = Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase) | journal = European Journal of Pharmacology | volume = 200 | issue = 1 | pages = 187–90 | date = July 1991 | pmid = 1722753 | doi = 10.1016/0014-2999(91)90686-K }}</ref>

{{Sticky}} {| class="wikitable sticky-header" |- ! Structure ! Name ! Chemical name ! CAS # |- | 120px|class=skin-invert-image | Tryptophan | (2''S'')-2-amino-3-(1''H''-indol-3-yl)propanoic acid | 73-22-3 |- | 120px|class=skin-invert-image | 5-Hydroxytryptophan (5-HTP) | (2''S'')-2-amino-3-(5-hydroxy-1''H''-indol-3-yl)propanoic acid | 4350-09-8 |- | 120px|class=skin-invert-image | 5-Methoxytryptophan (5-MTP) | (2''S'')-2-amino-3-(5-methoxy-1''H''-indol-3-yl)propanoic acid | 2504-22-5 |- | 120px|class=skin-invert-image | α-Methyltryptophan | (2''S'')-2-amino-3-(1''H''-indol-3-yl)-2-methylpropanoic acid | 16709-25-4 |- | 120px|class=skin-invert-image | α-Methyl-5-HTP | (2''S'')-2-amino-3-(5-hydroxy-1''H''-indol-3-yl)-2-methylpropanoic acid | 150852-19-0 |- | 120px|class=skin-invert-image | α-Methyl-5-MTP | (2''S'')-2-amino-3-(5-methoxy-1''H''-indol-3-yl)-2-methylpropanoic acid | ? |- | 120px|class=skin-invert-image | AMT (αMT; α-MT; Indopan) | 1-(1''H''-Indol-3-yl)propan-2-amine | 299-26-3 |- | 120px|class=skin-invert-image | 2,α-DMT (2-methyl-AMT) | 1-(2-methyl-1''H''-indol-3-yl)propan-2-amine | 4966-28-3 |- | 125px|class=skin-invert-image | 4-Methyl-AMT | 1-methyl-2-(4-methyl-1''H''-indol-3-yl)-ethylamine | 3569-29-7 |- | 130px|class=skin-invert-image | 5-Fluoro-AMT | 1-(5-fluoro-1H-indol-3-yl)propan-2-amine | 712-08-3 |- | 125px|class=skin-invert-image | 5-Chloro-AMT | 1-(5-Chloro-1H-indol-3-yl)propan-2-amine | 712-07-2 |- | 120px|class=skin-invert-image | 5-HO-AMT (αMS/α-methyl-5-HT) | 3-(2-aminopropyl)-1''H''-indol-5-ol | 304-52-9 |- | 120px|class=skin-invert-image | 5-MeO-AMT | 1-(5-methoxy-1''H''-indol-3-yl)propan-2-amine | 1137-04-8 |- | 125px|class=skin-invert-image | 5-Ethoxy-AMT | 1-(5-ethoxy-1''H''-indol-3-yl)propan-2-amine | 101832-83-1 |- | 125px|class=skin-invert-image | 5-Isopropoxy-AMT | 1-{5-[(propan-2-yl)oxy]-1''H''-indol-3-yl}propan-2-amine | |- | 125px|class=skin-invert-image | 5-Allyloxy-AMT | 1-{5-[(prop-2-en-1-yl)oxy]-1''H''-indol-3-yl}propan-2-amine | |- | 120px|class=skin-invert-image | 1-Propyl-5-MeO-AMT | 1-(5-methoxy-1-propylindol-3-yl)propan-2-amine | ? |- | 120px|class=skin-invert-image | BW-723C86 | 1-[5-(2-Thienylmethoxy)-1''H''-indol-3-yl]-2-propanamine | 160521-72-2 |- | 120px|class=skin-invert-image | 6-Fluoro-AMT | 1-(6-fluoro-1H-indol-3-yl)propan-2-amine | 712-11-8 |- | 120px|class=skin-invert-image | 7-Chloro-AMT | 1-(7-chloro-1H-indol-3-yl)propan-2-amine | 711-99-9 |- | 120px|class=skin-invert-image | AL-37350A (4,5-DHP-AMT) | (''S'')-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-''e'']indole | 362603-40-5 |- | 120px|class=skin-invert-image | Compound 5 <ref name="Chang-Fong_2002">{{cite journal | vauthors = Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA | title = Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors | journal = Bioorganic & Medicinal Chemistry Letters | volume = 12 | issue = 2 | pages = 155–8 | date = January 2002 | pmid = 11755343 | doi = 10.1016/s0960-894x(01)00713-2 }}</ref> | 1-(3H-benzo[e]indol-1-yl)propan-2-amine | |- | 120px|class=skin-invert-image | AET (αET; α-ET) | 1-(1''H''-indol-3-yl)butan-2-amine | 2235-90-7 |- | 120px|class=skin-invert-image | 4-Methyl-AET | 1-(4-Methyl-1''H''-indol-3-yl)butan-2-amine | 28289-30-7 |- | 120px|class=skin-invert-image | 4-HO-AET | 1-(4-hydroxy-1''H''-indol-3-yl)butan-2-amine | 28289-28-3 |- | 120px|class=skin-invert-image | 5-Fluoro-AET | 1-(5-fluoro-1''H''-indol-3-yl)butan-2-amine | 1380137-98-3 |- | 120px|class=skin-invert-image | 5-Chloro-AET | 1-(5-chloro-1''H''-indol-3-yl)butan-2-amine | ? |- | 125px|class=skin-invert-image | 5-Methyl-AET | 1-(5-methyl-1H-indol-3-yl)butan-2-amine | 1380148-21-9 |- | 125px|class=skin-invert-image | 5-MeO-AET | 1-(5-methoxy-1H-indol-3-yl)butan-2-amine | 4765-10-0 |- | 130px|class=skin-invert-image | 7-Methyl-AET | 1-(7-methyl-1''H''-indol-3-yl)butan-2-amine | 13712-80-6 |- | 125px|class=skin-invert-image | α,''N''-DMT (SK&F-7024, Ro 3-1715; ''N''-methyl-AMT) | 1-(1''H''-indol-3-yl)-N-methylpropan-2-amine | 299-24-1 |- | 125px|class=skin-invert-image | N,N-Dimethyl-AMT (α,''N'',''N''-TMT) | (2-(1''H''-Indol-3-yl)-1-methyl-ethyl)dimethylamine | 4761-32-4 |- | 125px|class=skin-invert-image | ''N''-Hydroxy-AMT (''N''-HO-AMT) | ''N''-[1-(1''H''-indol-3-yl)propan-2-yl]hydroxylamine | 63-33-2 |- | 125px|class=skin-invert-image | N-Methyl-5-MeO-AMT (α,''N'',''O''-TMS/α,''N'',''O''-trimethyl-5-HT) | [1-(5-methoxy-1''H''-indol-3-yl)propan-2-yl](methyl)amine | 4822-13-3 |- | 120px|class=skin-invert-image | ''N'',''N''-Dimethyl-5-MeO-AMT (5-MeO-α,''N'',''N''-TMT) | (2-(5-methoxy-1''H''-Indol-3-yl)-1-methyl-ethyl)dimethylamine | 101831-90-7 |- | 125px|class=skin-invert-image | α-Propyltryptamine (APT; αPT; α-PT) | 1-(1''H''-indol-3-yl)pentan-2-amine | |- | 125px|class=skin-invert-image | Indolylpropylaminopentane (IPAP; α,''N''-DPT) | 1-(1''H''-indol-3-yl)-''N''-propylpentan-2-amine | |- | 125px|class=skin-invert-image | α-Methyl-DiPT | (2-(1''H''-Indol-3-yl)-1-methyl-ethyl)diisopropylamine | |- | 130px|class=skin-invert-image | MPMI<ref>{{cite patent | url = https://patents.google.com/patent/US5607951A | inventor = Macor JE, Wythes MJ | title = Indole derivatives | country = US | number = 5607951 | assign1 = Pfizer, Inc. | gdate = 4 March 1997 }}</ref> | 3-[(1-methylpyrrolidin-2-yl)methyl]-1''H''-indole | 143321-54-4 |- | 130px|class=skin-invert-image | Lucigenol (4-HO-MPMI) | 3-(''N''-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole | ? |- | 130px|class=skin-invert-image | 5-MeO-MPMI (CP-108509) | 5-Methoxy-3-{[(2''R'')-1-methylpyrrolidin-2-yl]methyl}-1''H''-indole | 143321-57-7 |- | 130px|class=skin-invert-image | 5-Fluoro-MPMI<ref>{{cite patent | url = https://patentscope.wipo.int/search/docs2/pct/WO2022256554/pdf/cwqxbYm2px2kR95PXlFL3h7H7QXdzs3YjNCFNJZ86Do | inventor = Wallach J, Dybek M | title = Fluorinated Tryptamine Compounds, Analogues Thereof, and Methods Using Same. | country = WO | number = 2022256554 | assign1 = University Of The Sciences | pubdate = 8 December 2022 | postscript = . }}</ref> | 5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1''H''-indole | ? |- | 130px|class=skin-invert-image | 5-Bromo-MPMI | 5-bromo-3-[(1-methylpyrrolidin-2-yl)methyl]-1''H''-indole | 143322-57-0 |- | 130px|class=skin-invert-image | Eletriptan | 3-{[(2''R'')-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1''H''-indole | 143322-58-1 |- | 130px|class=skin-invert-image | Z5247692566<ref name="pmid38187536"/><ref>{{cite journal | vauthors = Callaway E |title=AlphaFold found thousands of possible psychedelics. Will its predictions help drug discovery? |journal=Nature News |date=18 January 2024 |volume=626 |issue=7997 |pages=14–15 |doi=10.1038/d41586-024-00130-8|pmid=38238624 |bibcode=2024Natur.626...14C |s2cid=267040499 }}</ref> | 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine | |- | 130px|class=skin-invert-image | BK-NM-AMT (α,''N''-dimethyl-β-ketotryptamine)<ref name="BloughDeckerLandavazo2019">{{cite journal | vauthors = Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB | title = The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes | journal = Psychopharmacology (Berl) | volume = 236 | issue = 3 | pages = 915–924 | date = March 2019 | pmid = 30341459 | pmc = 6475490 | doi = 10.1007/s00213-018-5063-9 | url = }}</ref><ref name="PubChem-BK-NM-AMT">{{cite web | title=1-(1H-indol-3-yl)-2-(methylamino)propan-1-one | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/82282492 | access-date=11 November 2024}}</ref><ref name="US20240335414A1">{{cite patent | country = US | number = 20240335414 | invent1 = Matthew J. Baggott | invent2 = Sean Dalziel | assign = Tactogen Inc. | title=Specialized combinations for mental disorders or mental enhancement | url=https://patents.google.com/patent/US20240335414A1/ | pubdate = 10 October 2024 }}</ref> | 1-(1''H''-indol-3-yl)-2-(methylamino)propan-1-one | |- | 130px|class=skin-invert-image | BK-5F-NM-AMT (5-fluoro-α,''N''-dimethyl-β-ketotryptamine)<ref name="PubChem-BK-5F-NM-AMT">{{cite web | title=1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/162765676 | access-date=11 November 2024}}</ref><ref name="IsomerDesign-BK-5F-NM-AMT">{{cite web | title=β-Oxo-5-fluoro-α-methyl-NMT | website=Isomer Design | date=10 November 2024 | url=https://isomerdesign.com/pihkal/explore/12714 | access-date=11 November 2024}}</ref><ref name="WO2022061242A1">{{cite patent | country = WO | number = 2022061242 | inventor = Matthew Baggott | status = | title = Advantageous tryptamine compositions for mental disorders or enhancement | pubdate = 2023 March 24 | gdate = | fdate = 2021 September 20 | pridate = 2021 September 20 | assign1 = Tactogen | url = https://patents.google.com/patent/WO2022061242A1/}}</ref><ref name="US20240335414A1" /> | 1-(5-fluoro-1''H''-indol-3-yl)-2-(methylamino)propan-1-one | |- | 130px|class=skin-invert-image | BK-5Cl-NM-AMT (5-chloro-α,''N''-dimethyl-β-ketotryptamine)<ref name="WO2022061242A1" /><ref name="PubChem-BK-5Cl-NM-AMT">{{cite web | title=1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/162765502 | access-date=11 November 2024}}</ref><ref name="IsomerDesign-BK-5Cl-NM-AMT">{{cite web | title=β-Oxo-5-chloro-α-methyl-NMT | website=Isomer Design | date=10 November 2024 | url=https://isomerdesign.com/pihkal/explore/12715 | access-date=11 November 2024}}</ref> | 1-(5-chloro-1''H''-indol-3-yl)-2-(methylamino)propan-1-one | |- | 130px|class=skin-invert-image | BK-5Br-NM-AMT (5-bromo-α,''N''-dimethyl-β-ketotryptamine)<ref name="WO2022061242A1" /><ref name="PubChem-BK-5Br-NM-AMT">{{cite web | title=1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/162765532 | access-date=11 November 2024}}</ref><ref name="IsomerDesign-BK-5Br-NM-AMT">{{cite web | title=β-Oxo-5-bromo-α-methyl-NMT | website=Isomer Design | date=10 November 2024 | url=https://isomerdesign.com/pihkal/explore/12725 | access-date=11 November 2024}}</ref> | 1-(5-bromo-1''H''-indol-3-yl)-2-(methylamino)propan-1-one | |}

===List of substituted β-ketotryptamines=== A number of β-ketotryptamines (beta-ketotryptamines) are known.<ref name="BloughDeckerLandavazo2019" /><ref name="US20240335414A1" /><ref name="WO2022061242A1" /> These compounds are α-alkyl-β-ketotryptamines and are analogous to the cathinones (β-ketoamphetamines) of the related phenethylamine family. Known β-ketotryptamines include BK-NM-AMT, BK-5F-NM-AMT, BK-5Cl-NM-AMT, and BK-5Br-NM-AMT.<ref name="BloughDeckerLandavazo2019" /><ref name="US20240335414A1" /><ref name="WO2022061242A1" /> They act as monoamine releasing agents.<ref name="BloughDeckerLandavazo2019" /><ref name="US20240335414A1" /><ref name="WO2022061242A1" />

===Cyclized tryptamines=== Examples of cyclized tryptamines include:

* β-Carbolines such as harmala alkaloids like harmaline * Ibogalogs (hexahydroazepinoindoles) such as ibogainalog, tabernanthalog, PNU-22394, and PHA-57378 * Iboga alkaloids like ibogaine, noribogaine, ibogamine, and tabernanthine * Ergolines and lysergamides such as lysergic acid diethylamide (LSD) and ergot alkaloids like ergine (lysergic acid amide; LSA) * Partial ergolines and lysergamides like RU-27849, FHATHBIN, NDTDI, and CT-5252 * ''Mitragyna'' alkaloids such as mitragynine * Yohimbans such as ''Rauvolfia'' and ''Corynanthe'' alkaloids like yohimbine and rauwolscine * Pyrrolidinylethylindoles like pyr-T, 4-HO-pyr-T, 5-MeO-pyr-T, 4-F-5-MeO-pyr-T, and L-760790 * Pyrrolidinylmethylindoles like MPMI, 4-HO-MPMI (lucigenol), 5F-MPMI, 5-MeO-MPMI, CP-135807, eletriptan, and MSP-2020 * Imidazolylindoles like AGH-107, AGH-192, and AH-494 * Piperidinylethylindoles like pip-T, 5-MeO-pip-T, and indoramin * Morpholinylethylindoles like mor-T and 5-MeO-mor-T * Tetrahydropyridinylindoles like RS134-49 (4-Me-THPI), RU-28253 (5-MeO-THPI), and NEtPhOH-THPI * Pertines (phenylpiperazinylethylindoles) like alpertine, milipertine, oxypertine, and solypertine * Tetrahydrocarbazolamines like ciclindole, flucindole, frovatriptan, LY-344864, and ramatroban * Tetrahydropyrroloquinolines like bufothionine, ''O''-methylnordehydrobufotenine, and dehydrobufotenine * Others like 5-MeO-IsoqT, barettin, cyclic 3-hydroxymelatonin, metralindole, and Z5247692566

Other closely related cyclized tryptamine-like compounds include the following:

* Piperidinylindoles like SN-22, BRL-54443, naratriptan, LY-334370, and sertindole * Tetrahydropyridinylindoles like RU-24969, EMD-386088, and LY-367,265 * Tetrahydropyridinylindazoles like VU6067416 * Tetrahydropyridinylpyrrolopyridines like (''R'')-69, (''R'')-70, CP-93129, and CP-94253 * Pyridopyrroloquinoxalines (tetracyclic γ-carbolines) like lumateperone, IHCH-7113, IHCH-7086, and ITI-1549

==Related compounds== A number of related compounds are known, with a similar structure but having the indole core flipped (isotryptamines) and/or replaced with related cores such as indene, indoline, indazole, indolizine, benzothiophene, or benzofuran. Like tryptamines, these related compounds are primarily active as agonists at the 5-HT₂ family of serotonin receptors, with applications in the treatment of glaucoma, cluster headaches, or as anorectics.

{{Sticky}} {| class="wikitable sticky-header" |- ! Structure ! Name ! Chemical name ! CAS # |- | 120px|class=skin-invert-image | C-DMT (1-carba-DMT) | 2-(3''H''-inden-1-yl)-''N'',''N''-dimethylethanamine | |- | 120px|class=skin-invert-image | O-DMT (1-oxa-DMT, DMBF) | 2-(1-benzofuran-3-yl)-''N'',''N''-dimethylethanamine | |- | 120px|class=skin-invert-image | MiPBF (1-oxa-MiPT) | ''N''-[2-(1-benzofuran-3-yl)ethyl]-''N''-methylpropan-2-amine | |- | 120px|class=skin-invert-image | Dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT) | 2-(5-Methoxy-1-benzofuran-3-yl)-''N'',''N''-dimethylethanamine | 140853-58-3 |- | 120px|class=skin-invert-image | 5-MeO-DiBF (1-oxa-5-MeO-DiPT) | ''N''-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-''N''-(propan-2-yl)propan-2-amine | |- | 120px|class=skin-invert-image | 3-APB (1-oxa-AMT) | 3-(2-aminopropyl)benzofuran | 105909-13-5 |- | 120px|class=skin-invert-image | Mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT) | 3-(2-aminopropyl)-5-methoxybenzofuran | 140853-59-4 |- | 120px|class=skin-invert-image | S-DMT (1-thia-DMT) | 2-(1-benzothiophen-3-yl)-''N'',''N''-dimethylethanamine | 10275-64-6 |- | 120px|class=skin-invert-image | 3-APBT (SKF-6678; 1-thia-AMT) | 1-(1-benzothiophen-3-yl)propan-2-amine | 1201-27-0 |- | 120px|class=skin-invert-image | Isotryptamine (isoT) | 2-indol-1-ylethanamine | 13708-58-2 |- | 120px|class=skin-invert-image | isoAMT | 1-indol-1-ylpropan-2-amine | 1227465-67-9 |- | 120px|class=skin-invert-image | (''S'')-5,6-Difluoro-isoAMT <ref name="Chang-FongAddoDukat2002">{{cite journal | vauthors = Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA | title = Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors | journal = Bioorg Med Chem Lett | volume = 12 | issue = 2 | pages = 155–158 | date = January 2002 | pmid = 11755343 | doi = 10.1016/s0960-894x(01)00713-2 | url = | quote = Detailed re-examination of a compound previously reported to display 100-fold 5-HT2C selectivity [i.e., S(+)-5,6-difluoro-α-methylisotryptamine] revealed that its selectivity versus 5-HT2A receptors was, at best, only 10-fold.}}</ref> | (S)-1-(5,6-difluoroindol-1-yl)propan-2-amine | |- | 120px|class=skin-invert-image | Ro60-0175 ((''S'')-5-F-6-Cl-isoAMT) | (S)-(6-chloro-5-fluoro-1H-indol-1-yl)propan-2-amine | 169675-09-6 |- | 120px|class=skin-invert-image | isoDMT | 2-indol-1-yl-N,N-dimethylethanamine | 87482-09-5 |- | 120px|class=skin-invert-image | 5-MeO-isoDMT | 2-(5-methoxyindol-1-yl)-N,N-dimethylethanamine | 244122-80-3 |- | 120px|class=skin-invert-image | 6-MeO-isoDMT | 2-(6-methoxyindol-1-yl)-N,N-dimethylethanamine | 87482-11-9 |- | 120px|class=skin-invert-image | Zalsupindole (DLX-001; AAZ-A-154; (''R'')-5-MeO-α-Me-isoDMT) | (2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine | 2481740-94-5 |- | 120px|class=skin-invert-image | 2ZEDMA | 2-indolizin-1-yl-''N'',''N''-dimethylethanamine | |- | 120px|class=skin-invert-image | 1ZP2MA | 1-indolizin-1-yl-''N''-methylpropan-2-amine | |- | 120px|class=skin-invert-image | 1Z2MAP1O | 1-indolizin-3-yl-2-(methylamino)propan-1-one | 2110204-31-2 |- | 120px|class=skin-invert-image | Example 16 <ref>{{cite journal | author = Kargbo RB | date = Jan 2024 | title = Neuropharmacological Advances: Harnessing 5-HT2A Receptor Modulators and Psychoplastogens | journal = ACS Med Chem Lett | volume = 15 | issue = 2| pages = 171–173 | doi = 10.1021/acsmedchemlett.4c00003 | pmid = 38352827 | pmc = 10860177 }}</ref><ref>[https://patents.google.com/patent/WO2023114844A1 Powell NA, Chytil M. Imidazopyridine psychoplastogens and uses thereof. WO 2023/114844]</ref> | 1-(7-methoxyimidazo[1,5-a]pyridin-3-yl)-N,N-dimethylpropan-2-amine | |- | 120px|class=skin-invert-image | Example 1 <ref>{{cite patent |country= US |number= 7012090|status= granted |title= Pyranoindoles for treating glaucoma |pubdate= 17 March 2000 |gdate= 14 March 2006 |fdate= |pridate= |inventor=Chen HH, May JA |assign1= Alcon, Inc. }}</ref> | 1-(3-methyl-8,9-dihydropyrano[2,3-g]indol-1(7H)-yl)propan-2-amine | |- | 120px|class=skin-invert-image | VER-3323 | (2S)-1-(6-bromo-2,3-dihydroindol-1-yl)propan-2-amine | 259857-99-3 |- | 120px|class=skin-invert-image | AL-34662 (indazole-5-HO-AMT) | 1-((S)-2-Aminopropyl)-1H-indazol-6-ol | 210580-75-9 |- | 120px|class=skin-invert-image | ''O''-Methyl-AL-34662 (indazole-5-MeO-AMT) | 1-((S)-6-methoxy-2-aminopropyl)-1H-indazole | 210580-60-2 |- | 120px|class=skin-invert-image | 7-Methyl-AL-34662 | 1-((S)-2-Aminopropyl)-7-methyl-1H-indazol-6-ol | 874668-67-4 |- | 120px|class=skin-invert-image | 7-Chloro-AL-34662 | 1-((S)-2-Aminopropyl)-7-chloro-1H-indazol-6-ol | 874881-86-4 |- | 120px|class=skin-invert-image | AL-38022A | (S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine | 478132-11-5 |- | 120px|class=skin-invert-image | Example 9 <ref>{{cite patent |country= US |number= 6881749|status= granted |title= Pyranoindazoles and their use for the treatment of glaucoma|pubdate= 3 June 2004 |gdate= 19 April 2005 |fdate= |pridate= |inventor= Chen HH, May JA, Severns BS |assign1= Alcon, Inc. }}</ref> | (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine | 478132-12-6 |- | 120px|class=skin-invert-image | Example 3 <ref>{{cite patent |country= US |number= 7425572 |status= granted |title= Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma|pubdate= 8 June 2006 |gdate= 16 September 2008 |fdate= |pridate= |inventor= Chen HH, May JA |assign1= Alcon, Inc.}}</ref> | (S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine | 890087-75-9 |- | 120px|class=skin-invert-image | Example 1 <ref>{{cite patent |country= US |number= 7268131|status= granted |title= Substituted [1,4]oxazino[2,3-g]indazoles for the treatment of glaucoma |pubdate= 15 December 2005 |gdate= 11 September 2007 |fdate= |pridate= |inventor= |invent1= Dantanarayana AP, May JA |assign1= Alcon, Inc. }}</ref> | (S)-8,9-dihydro-α,9-dimethylpyrazolo[3,4-f][1,4]benzoxazine-1(7H)-ethanamine | 1373917-69-1 |- | 120px|class=skin-invert-image | YM-348 | (2''S'')-1-(7-ethyl-1''H''-furo[2,3-''g'']indazol-1-yl)propan-2-amine | 372163-84-3 |- | 120px|class=skin-invert-image | 2-Desethyl-YM-348 <ref>{{cite journal | vauthors = Shimada I, Maeno K, Kazuta K, Kubota H, Kimizuka T, Kimura Y, Hatanaka K, Naitou Y, Wanibuchi F, Sakamoto S, Tsukamoto S | display-authors = 6 | title = Synthesis and structure-activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT2C receptor agonists | journal = Bioorganic & Medicinal Chemistry | volume = 16 | issue = 4 | pages = 1966–82 | date = February 2008 | pmid = 18035544 | doi = 10.1016/j.bmc.2007.10.100 }}</ref> | (2''S'')-1-(1''H''-furo[2,3-''g'']indazol-1-yl)propan-2-amine | 748116-94-1 |- | 120px|class=skin-invert-image | I-32 <ref>{{cite patent | url = https://patentscope.wipo.int/search/docs2/pct/WO2022120475/pdf/--4i5qAp7DFLOcADPaLlykxoeczTsz-AlbTjjpmTBSU| inventor = Slassi A, Araujo J, Higgins G | title = 3-Cyclic Amine-Indole Derivatives as Serotonergic Agents for the Treatment of CNS Disorders. | country = WO | number = 2022120475 | assign = Mindset Pharma Inc. | pubdate = 16 June 2022 }}</ref> | 3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol | |- | 120px|class=skin-invert-image | 2-Azapsilocin (Psilocin indazole analogue, '''P-6''')<ref>{{cite patent | url = https://patents.google.com/patent/WO2023115165A1/en?oq=WO2023115165 | country = WO | number = 2023115165 | inventor = Banister S, Jorgensen W, Jinlong T | title = Compounds | assignee = Psylo Pty Ltd. | pubdate = 29 June 2023 }}</ref> | 3-[2-(dimethylamino)ethyl]-1H-indazol-4-ol | |- | 120px|class=skin-invert-image | 4-Aza-5-MeO-DPT ('''P-11''') | N-[2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)ethyl]-N-propylpropan-1-amine | |- | 120px|class=skin-invert-image | 5-Aza-4-MeO-DiPT ('''P-36''') | N-[2-(4-methoxy-1H-pyrrolo[3,2-c]pyridin-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine | |- | 120px|class=skin-invert-image | 7-Aza-5-MeO-DiPT ('''P-19''') | N-[2-(5-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine | |- | 120px|class=skin-invert-image | RS134-49 (4-Me-THPI) | 4-methyl-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole | 2945139-94-4 |- | 120px|class=skin-invert-image | RU-28253 (5-MeO-THPI) | 5-methoxy-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole | ? |- | 120px|class=skin-invert-image | NEtPhOH-THPI (compound 24c) | 3-(1-(2-hydroxyphenylethyl)-1,2,3,6-tetrahydropyridin-5-yl)-1H-indole | ? |- | 120px|class=skin-invert-image | VU6067416<ref>{{cite journal | author = Jayakodiarachchi N | display-authors = etal | year = 2024 | title = Evaluation of the Indazole Analogs of 5-MeO-DMT and Related Tryptamines as Serotonin Receptor 2 Agonists | url = | journal = ACS Med. Chem. Lett. | volume = 15| issue = 2| pages = 302–309| doi = 10.1021/acsmedchemlett.3c00566 | pmid = 38352850 | pmc = 10860182 }}</ref> | 3-(1,2,5,6-tetrahydropyridin-3-yl)-5-bromo-1H-indazole | 3027515-24-5 |- | 120px|class=skin-invert-image | (''R'')-69 | 3-[(5''R'')-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1''H''-pyrrolo[2,3-b]pyridine | 2765652-48-8 |- | 120px|class=skin-invert-image | (''R'')-70 | 3-[(3''R'')-1,3-dimethyl-3,6-dihydro-2''H''-pyridin-5-yl]-1''H''-pyrrolo[2,3-b]pyridine | ? |- | 120px|class=skin-invert-image | SN-22 | 3-(1-methylpiperidin-4-yl)-1H-indole | 17403-07-5 |- | 120px|class=skin-invert-image | RU-24,969 | 5-methoxy-3-(1,2,5,6-tetrahydro-4-pyridinyl)-1H-indole | 107008-28-6 |- | 120px|class=skin-invert-image | EMD-386088 | 5-chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole | 54635-62-0 |- | 120px|class=skin-invert-image | T-70<ref>{{cite web | title=T-70 - PiHKAL·info | website=Isomer Design | date=12 June 2025 | url=https://isomerdesign.com/pihkal/explore/5068 | access-date=1 March 2026}}</ref> | ''N'',''N''-dimethyl-2-(6''H''-thieno[2,3-''b'']pyrrol-4-yl)ethan-1-amine | ? |- | 120px|class=skin-invert-image | T-72<ref>{{cite web | title=T-72 - PiHKAL·info | website=Isomer Design | date=12 June 2025 | url=https://isomerdesign.com/pihkal/explore/5067 | access-date=1 March 2026}}</ref> | ''N'',''N''-dimethyl-2-(4''H''-thieno[3,2-''b'']pyrrol-6-yl)ethan-1-amine | ? |- | 120px|class=skin-invert-image | Gramine | 1-(1''H''-indol-3-yl)-''N'',''N''-dimethylmethanamine | 87-52-5 |- | 120px|class=skin-invert-image | Homotryptamine | 3-(1''H''-indol-3-yl)propan-1-amine | 6245-89-2 |- | 120px|class=skin-invert-image | Dimethylhomotryptamine (DMHT) | 3-(1''H''-indol-3-yl)-''N'',''N''-dimethylpropan-1-amine | 13117-35-6 |- | 120px|class=skin-invert-image | Benzydamine | 3-(1-benzyl-1''H''-indazol-3-yloxy)-''N'',''N''-dimethylpropan-1-amine | 642-72-8 |- | 120px|class=skin-invert-image | Indalpine | 3-(2-piperidin-4-ylethyl)-1''H''-indole | 63758-79-2 |- | 120px|class=skin-invert-image | Methylindolylethylpyridine (IN-399) | 1-methyl-3-(2-pyridin-4-ylethyl)indole | 16571-53-2 |- | 120px|class=skin-invert-image | Benzindopyrine (pyrbenzindole; IN-461) | 1-benzyl-3-(2-pyridin-4-ylethyl)indole | 16571-59-8 |}

==Overview table== {{Simple tryptamines and their common derivatives}}

==See also== {{Columns-list|colwidth=25em| * Arylalkylamine * Substituted β-carboline * Ibogalog * Iboga alkaloid * Lysergamide * TiHKAL * List of miscellaneous 5-HT_2A receptor agonists * Substituted isotryptamine * Indazolylethylamine * Indolizinylethylamine * Tetrahydropyridinylpyrrolopyridine * Substituted 2-aminoindane * Substituted amphetamine * Substituted benzofuran * Substituted cathinone * Substituted methylenedioxyphenethylamine * Substituted phenethylamine * 2C, DOx, 25-NB }}

==References== {{Reflist}}

==External links== * [https://pageviews.wmcloud.org/massviews/?platform=all-access&agent=user&source=category&range=all-time&subjectpage=0&subcategories=0&sort=views&direction=1&view=list&target=https://en.wikipedia.org/wiki/Category:Psychedelic_tryptamines Psychedelic Tryptamines - Wikipedia Massviews Analysis (Wikipedia Page Views of Individual Psychedelic Tryptamines)]

{{Tryptamines}} {{Psychedelics}} {{Serotonin receptor modulators}} {{Chemical classes of psychoactive drugs}}

Category:Tryptamines Category:Alpha-Alkyltryptamines Category:Chemical classes of psychoactive drugs Category:Functional groups