Dipropyltryptamine

{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Use dmy dates|date=March 2024}} {{Infobox drug | Watchedfields = verified | verifiedrevid = 444963386 | image = DPT.svg | image_class = skin-invert-image | width = 215px | image2 = DPT-3d-sticks.png | image_class2 = bg-transparent | width2 = 250px

<!-- Clinical data --> | pregnancy_AU = | pregnancy_US = | pregnancy_category = | routes_of_administration = Oral, smoking, intramuscular injection, intravenous injection<ref name="TiHKAL" /> | class = Serotonin receptor agonist; Serotonin 5-HT_2A receptor agonist; Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =

<!-- Legal status --> | legal_AU = | legal_CA = | legal_DE = NpSG | legal_UK = Class A | legal_US = | legal_status =

<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | onset = Oral: Fast<ref name="TiHKAL" /><br />Injection: 10–15 minutes<ref name="TiHKAL" /> | elimination_half-life = | duration_of_action = 2–4 hours (but up to 12 hours at very high doses)<ref name="TiHKAL" /><ref name="TittarelliManocchiPantano2015" /> | excretion =

<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 61-52-9 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = S7272VWU50 | PubChem = 6091 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 5866 | synonyms = DPT; ''N'',''N''-Dipropyltryptamine; "The Light"

<!-- Chemical data --> | IUPAC_name = ''N''-[2-(1''H''-indol-3-yl)]ethyl-''N''-propylpropan-1-amine | C=16 | H=24 | N=2 | SMILES = CCCN(CCC)CCC1=CNC2=C1C=CC=C2 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C16H24N2/c1-3-10-18(11-4-2)12-9-14-13-17-16-8-6-5-7-15(14)16/h5-8,13,17H,3-4,9-12H2,1-2H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = BOOQTIHIKDDPRW-UHFFFAOYSA-N

<!-- Physical data --> | melting_point = 174.5 | melting_high = 178 }}

'''Dipropyltryptamine''' ('''DPT'''), also known as '''''N'',''N''-dipropyltryptamine''' or as "'''The Light'''", is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT).<ref name="TiHKAL">{{CiteTiHKAL }}</ref><ref name="MalacaLoFaroTamborra2020">{{cite journal | vauthors = Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA | date = December 2020 | title = Toxicology and Analysis of Psychoactive Tryptamines | journal = International Journal of Molecular Sciences | volume = 21 | issue = 23 | page = 9279 | doi = 10.3390/ijms21239279 | pmc = 7730282 | pmid = 33291798 | doi-access = free }}</ref> It is taken orally or by other routes.<ref name="TiHKAL" />

The drug acts as a serotonin receptor modulator, including as a serotonin 5-HT_2A receptor agonist.<ref name="Ray_2010">{{cite journal | vauthors = Ray TS | date = February 2010 | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | article-number = e9019 | doi = 10.1371/journal.pone.0009019 | pmc = 2814854 | pmid = 20126400 | bibcode = 2010PLoSO...5.9019R | doi-access = free }}</ref><ref name="Kozell_2023">{{cite journal | vauthors = Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI | date = April 2023 | title = Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)_2A Receptor (5-HT_2AR), 5-HT_2CR, 5-HT_1AR, and Serotonin Transporter | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 385 | issue = 1 | pages = 62–75 | doi = 10.1124/jpet.122.001454 | pmc = 10029822 | pmid = 36669875 }}</ref><ref name="Blough_2014">{{cite journal | vauthors = Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB | date = October 2014 | title = Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes | journal = Psychopharmacology | volume = 231 | issue = 21 | pages = 4135–4144 | doi = 10.1007/s00213-014-3557-7 | pmc = 4194234 | pmid = 24800892 }}</ref><ref name="Nagai_2007">{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | date = March 2007 | 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 = 132–137 | doi = 10.1016/j.ejphar.2006.11.075 | pmid = 17223101 }}</ref><ref name="Nelson_1993" /> It is a close structural homologue of DMT and diethyltryptamine (DET).<ref name="TiHKAL" /> Derivatives of DPT include 4-HO-DPT and 5-MeO-DPT, among others.<ref name="TiHKAL" />

DPT was first described in the literature by 1954.<ref name="Szara1970" /><ref name="SpeeterAnthony1954" /><ref name="Barlow_1959" /><ref name="Barlow_1959a" /><ref name="Vane_1959" /> It was encountered as a novel designer drug by 1968<ref name="Microgram1968" /> and was reported as a possible treatment for alcoholism in 1973.<ref name="TittarelliManocchiPantano2015" /><ref name="MalacaLoFaroTamborra2020" /><ref name="SoskinGrofRichards1973">{{cite journal | vauthors = Soskin RA, Grof S, Richards WA | date = June 1973 | title = Low doses of Dipropyltryptamine in psychotherapy | journal = Archives of General Psychiatry | volume = 28 | issue = 6 | pages = 817–821 | doi = 10.1001/archpsyc.1973.01750360047006 | pmid = 4575167 }}</ref> The drug is the sacrament of the Temple of the True Inner Light, a New York City-based religious group.<ref name="TiHKAL" /><ref name="DeKorne2011">{{cite book | vauthors = DeKorne J | date = 26 July 2011 | title = Psychedelic Shamanism, Updated Edition: The Cultivation, Preparation, and Shamanic Use of Psychotropic Plants | publisher = North Atlantic Books | page = 81 | isbn = 978-1-58394-290-1 | url = https://books.google.com/books?id=uNGl_aN-1wAC&pg=PA81 }}</ref><ref name="Kaplan1987">{{cite journal | vauthors = Kaplan E | date = October 1987 | title = Still hippies, after all these years | journal = Spy Magazine | issue = October 1987 | pages = 61 | url = https://books.google.com/books?id=VgDtgAXO7pAC&pg=PA61 }}</ref>

==Use and effects== In his book ''TiHKAL'' (''Tryptamines I Have Known and Loved''), Alexander Shulgin lists DPT's dose range as 100 to 250{{nbsp}}mg orally and its duration as 2 to 4{{nbsp}}hours.<ref name="TiHKAL" /><ref name="TittarelliManocchiPantano2015" /> A 500{{nbsp}}mg dose was also reported, which was described as "exhausting" and as lasting 12{{nbsp}}hours.<ref name="TiHKAL" /> The onset and time to peak effects were not given, but it was implied to have a fast onset.<ref name="TiHKAL" /> In addition to oral administration, DPT has been assessed by smoking at a dose of 100{{nbsp}}mg, by intramuscular injection at low doses of 15 to 30{{nbsp}}mg, moderate doses of 30 to 70{{nbsp}}mg, and "peak experience" doses of 75 to 125{{nbsp}}mg, and by intravenous injection at 12 to 36{{nbsp}}mg.<ref name="TiHKAL" /><ref name="Halberstadt_2020">{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD | 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 | journal = Neuropharmacology | volume = 167 | article-number = 107933 | doi = 10.1016/j.neuropharm.2019.107933 | pmc = 9191653 | pmid = 31917152 | quote = Table 4 Human potency data for selected hallucinogens. [...] }}</ref>

The effects of DPT have been reported to include visuals, being intensely visual at high doses, changes in time perception, feeling like one is in a different place like on a mountain in clouds or in a big castle, enhanced recall of memories and experiences, enhanced emotional expressiveness and self-exploration, entity encounters, and religious feelings.<ref name="TiHKAL" /><ref name="Pinchbeck2003" /><ref name="SoskinGrofRichards1973" /> Other effects included trouble talking, feeling uncomfortable, nervousness, feeling light, and body rush.<ref name="TiHKAL" /> Given at a high dose intravenously, it was described as every bit as powerful as a psychedelic as DMT.<ref name="TiHKAL" /> According to one account however, DPT and DMT, despite their chemical similarity, "reveal completely different worlds".<ref name="Pinchbeck2003">{{cite book | vauthors = Pinchbeck D | year = 2003 | title = Breaking Open The Head: A Psychedelic Journey Into the Heart of Contemporary Shamanism | publisher = Broadway Books | pages = 262–263,265,272,275–278 | isbn = 978-0-7679-0743-9 | author-link = Daniel Pinchbeck }}</ref>

Other reports have stated effects of DPT including visual and auditory hallucinations, increased color intensity, flashes of light and sparkles, apparitions of faces, increased music appreciation, ego dissolution, stimulation, euphoria, relaxation, paranoia, psychosis, anxiety, nausea, dizziness, muscle tremors, and increased heart rate, among others.<ref name="TittarelliManocchiPantano2015">{{cite journal | vauthors = Tittarelli R, Mannocchi G, Pantano F, Romolo FS | date = January 2015 | title = Recreational use, analysis and toxicity of tryptamines | journal = Current Neuropharmacology | volume = 13 | issue = 1 | pages = 26–46 | doi = 10.2174/1570159X13666141210222409 | pmc = 4462041 | pmid = 26074742 | quote = Dipropyl-tryptamine (DPT) was firstly synthesized in the 1950s [34], but it was firstly reported for use in the scientific literature only in 1973 [35], as an adjunct in psychotherapy of alcoholics. It is found either as its crystalline hydrochloride salt or as an oily or crystalline base and, as DET, it has not been found to occur naturally. There are few peer-reviewed experimental studies that try to explain the ways of interaction among DPT and serotonin receptors: Nagai revealed a strong inhibition of 5-HT reuptake in rat synaptosomes [16], and Thiagaraj also observed a moderate affinity partial agonism at the human 5-HT1A receptor [34]. Experiences related to DPT assumption are mostly psychedelic sensations, such as an increase of music and colors intensity, the vision of pleasant flashes of light and sparkles, a complete ego loss, and apparitions of faces. The dosage of DPT, for oral administration, is 100-250 mg and the duration of the psychoactive effects varies from 2 to 4 hours. }}</ref> Its duration is described as much shorter than those of certain other psychedelics like LSD, which can be advantageous in a clinical setting.<ref name="Dutta2012">{{cite journal | vauthors = Dutta V | date = 2012 | title = Repression of death consciousness and the psychedelic trip | journal = Journal of Cancer Research and Therapeutics | volume = 8 | issue = 3 | pages = 336–342 | doi = 10.4103/0973-1482.103509 | pmid = 23174711 | doi-access = free | quote = Dipropyltryptamine (DPT), another psychedelic was also examined in two cancer studies in lieu of the LSD, since its properties were similar to LSD but was less time consuming.[38] It took about 1 ½ to 6 hours to act, and its effects too wore off easily unlike the LSD that demanded a considerable amount of time. Post-therapeutically DPT’s benefits would mimic LSD. It was suggested to be a better alternative than LSD, but because of its quick onset, patients often found the sudden psychological upheaval overwhelming.[39] }}</ref><ref name="Richards_1977">{{cite journal | vauthors = Richards WA, Rhead JC, Dileo FB, Yensen R, Kurland AA | date = 1977 | title = The Peak Experience Variable in DPT-Assisted Psychotherapy with Cancer Patients | journal = Journal of Psychedelic Drugs | volume = 9 | issue = 1 | pages = 1–10 | doi = 10.1080/02791072.1977.10472020 | issn = 0022-393X }}</ref><ref name="Richards_1980" /> However, it is also said to have a rapid onset that can be psychologically overwhelming.<ref name="Dutta2012" /><ref name="Richards_1980">{{cite journal | vauthors = Richards WA, Rhead JC, Grof S, Goodman LE, Di Leo F, Rush L | date = 1980 | title = DPT as an Adjunct in Brief Psychotherapy with Cancer Patients | journal = OMEGA - Journal of Death and Dying | volume = 10 | issue = 1 | pages = 9–26 | doi = 10.2190/NGUB-V4RM-T7DC-XTH3 | issn = 0030-2228 }}</ref>

==Side effects== Although tryptamines such as psilocybin and dimethyltryptamine (DMT) have relatively well‑characterized safety, synthetic analogues like DPT lack thorough toxicological evaluation and are mainly associated with anecdotal reports of intoxication and a few cases of fatal outcomes when used recreationally.<ref name="Araujo_2015">{{cite journal | vauthors = Araújo AM, Carvalho F, Bastos M, Guedes de Pinho P, Carvalho M | date = August 2015 | title = The hallucinogenic world of tryptamines: an updated review | journal = Archives of Toxicology | volume = 89 | issue = 8 | pages = 1151–1173 | doi = 10.1007/s00204-015-1513-x | pmid = 25877327 | bibcode = 2015ArTox..89.1151A }}</ref> The pharmacological similarity of DPT to DMT suggests a generally low intrinsic toxicity at controlled doses but a pronounced risk of acute adverse reactions, including agitation, tachycardia, hyperthermia, and serotonergic crisis, particularly in combination with monoamine oxidase inhibitors or other serotonergic substances.<ref name="Araujo_2015" />

A meta-analysis of tryptamine psychedelics have further demonstrated cognitive effects through serotonin 5-HT_2A receptor modulation but have not identified persistent neurotoxicity.<ref name="Castelhano_2021">{{cite journal | vauthors = Castelhano J, Lima G, Teixeira M, Soares C, Pais M, Castelo-Branco M | date = 2021 | title = The Effects of Tryptamine Psychedelics in the Brain: A meta-Analysis of Functional and Review of Molecular Imaging Studies | journal = Frontiers in Pharmacology | volume = 12 | article-number = 739053 | doi = 10.3389/fphar.2021.739053 | pmc = 8511767 | pmid = 34658876 | doi-access = free }}</ref> The main safety concerns are acute psychophysiological and behavioral disturbances rather than long‑term organ toxicity. Overall, DPT is a potent, short‑acting serotonergic hallucinogen with limited safety data and a toxicity profile comparable to related tryptamines such as DMT and 5-MeO-DMT.<ref name="Araujo_2015" /><ref name="Castelhano_2021" />

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

==Pharmacology== ===Pharmacodynamics=== {| class="wikitable floatleft" style="font-size:small;" |+ DPT activities |- ! Target !! Affinity (K_i, nM) !! Species |- | 5-HT_1A || 31.8–1,641 (K_i)<br />274–>10,000 ({{Abbrlink|EC₅₀|half-maximal effective concentration}})<br />99% ({{Abbrlink|E_max|maximal efficacy}}) || Human<br />Human<br />Human |- | 5-HT_1B || 854–8,081 (K_i)<br />1,210 ({{Abbr|EC₅₀|half-maximal effective concentration}}) || Human<br />Human |- | 5-HT_1D || 619 || Human |- | 5-HT_1E || 2,338 || Human |- | 5-HT_2A || 3.0–2,579 (K_i)<br />26.1–943^a ({{Abbr|EC₅₀|half-maximal effective concentration}})<br />85^a–97% ({{Abbr|E_max|maximal efficacy}}) || Human<br />Human<br />Human |- | 5-HT_2B || 42 || Human |- | 5-HT_2C || 281–3,500 (K_i)<br />444^a ({{Abbr|EC₅₀|half-maximal effective concentration}})<br />93%^a ({{Abbr|E_max|maximal efficacy}}) || Human<br />Human<br />Human |- | 5-HT₃ || >10,000 || Human |- | 5-HT₄ || {{Abbr|ND|No data}} || {{Abbr|ND|No data}} |- | 5-HT_5A || 4,373 || Human |- | 5-HT₆ || 4,543 || Human |- | 5-HT₇ || 284 || Human |- | D₁ || >10,000 || Human |- | D₂ || 9,249 || Human |- | D₃ || 1,361 || Human |- | D₄ || 2,014 || Human |- | D₅ || >10,000 || Human |- | α_1A || 881 || Human |- | α_1B || 443 || Human |- | α_1D || {{Abbr|ND|No data}} || {{Abbr|ND|No data}} |- | α_2A || 458 || Human |- | α_2B || 339 || Human |- | α_2C || 514 || Human |- | β₁–β₂ || >10,000 || Human |- | H₁ || 125 || Human |- | H₂–H₄ || >10,000 || Human |- | M₁–M₅ || >10,000 || Human |- | I₁ || 340 || Human |- | σ₁ || 397 || Human |- | σ₂ || 2,917 || Human |- | {{Abbrlink|SERT|Serotonin transporter}} || 157–480 (K_i)<br />157–23,000 ({{Abbrlink|IC₅₀|half-maximal inhibitory concentration}})<br />100,000 ({{Abbr|EC₅₀|half-maximal effective concentration}}) || Human<br />Human<br />Rat |- | {{Abbrlink|NET|Norepinephrine transporter}} || >10,000 (K_i)<br />2,900–3,202 ({{Abbr|IC₅₀|half-maximal inhibitory concentration}})<br />100,000 ({{Abbr|EC₅₀|half-maximal effective concentration}}) || Human<br />Human<br />Rat |- | {{Abbrlink|DAT|Dopamine transporter}} || 1,500 (K_i)<br />2,218–9,100 ({{Abbr|IC₅₀|half-maximal inhibitory concentration}})<br />100,000 ({{Abbr|EC₅₀|half-maximal effective concentration}}) || Human<br />Human<br />Rat |- class="sortbottom" | colspan="3" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug binds to the site. '''Footnotes:''' ^a = Stimulation of {{Abbrlink|IP₁|inositol phosphate|}} formation. '''Refs:''' <ref name="Ray_2010" /><ref name="Kozell_2023" /><ref name="Blough_2014" /><ref name="Nagai_2007" /><ref name="Nelson_1993">{{cite journal | vauthors = Nelson DL, Lucaites VL, Audia JE, Nissen JS, Wainscott DB | date = June 1993 | title = Species differences in the pharmacology of the 5-hydroxytryptamine2 receptor: structurally specific differentiation by ergolines and tryptamines | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 265 | issue = 3 | pages = 1272–1279 | doi = 10.1016/S0022-3565(25)38269-8 | pmid = 8510008 }}</ref><ref name="KiDatabase">{{cite web | title = PDSP Database | language = zu | website = UNC | url = https://pdsp.unc.edu/databases/pdsp.php?testFreeRadio=testFreeRadio&testLigand=dipropyltryptamine&kiAllRadio=all&doQuery=Submit+Query | access-date = 11 December 2024 }}</ref><ref name="Tyagi_2023">{{cite journal | vauthors = Tyagi R, Saraf TS, Canal CE | date = October 2023 | title = The Psychedelic ''N'',''N''-Dipropyltryptamine Prevents Seizures in a Mouse Model of Fragile X Syndrome via a Mechanism that Appears Independent of Serotonin and Sigma1 Receptors | journal = ACS Pharmacology & Translational Science | volume = 6 | issue = 10 | pages = 1480–1491 | doi = 10.1021/acsptsci.3c00137 | pmc = 10580393 | pmid = 37854624 }}</ref> |}

DPT is a serotonin receptor agonist in the rat uterus and stomach strip, with several-fold greater potency than dimethyltryptamine (DMT).<ref name="BarlowKhan1959">{{cite journal | vauthors = Barlow RB, Khan I | title = Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations | journal = Br J Pharmacol Chemother | volume = 14 | issue = 1 | pages = 99–107 | date = March 1959 | pmid = 13651585 | pmc = 1481812 | doi = 10.1111/j.1476-5381.1959.tb00934.x | url = }}</ref><ref name="Vane1959">{{cite journal | vauthors = Vane JR | title = The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation | journal = Br J Pharmacol Chemother | volume = 14 | issue = 1 | pages = 87–98 | date = March 1959 | pmid = 13651584 | pmc = 1481817 | doi = 10.1111/j.1476-5381.1959.tb00933.x | url = }}</ref> It produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.<ref name="Halberstadt_2020" /><ref name="Fantegrossi_2008" /> Studies on rodents have found that the effectiveness with which a selective 5-HT_2A receptor antagonist blocks the behavioral actions of DPT strongly suggests that the 5-HT_2A receptor is an important site of action for the drug, but the modulatory actions of a serotonin 5-HT_1A receptor antagonist also imply a serotonin 5-HT_1A receptor-mediated component to the actions of DPT.<ref name="Fantegrossi_2008">{{cite journal | vauthors = Fantegrossi WE, Reissig CJ, Katz EB, Yarosh HL, Rice KC, Winter JC | date = January 2008 | title = Hallucinogen-like effects of N,N-dipropyltryptamine (DPT): possible mediation by serotonin 5-HT1A and 5-HT2A receptors in rodents | journal = Pharmacology, Biochemistry, and Behavior | volume = 88 | issue = 3 | pages = 358–365 | doi = 10.1016/j.pbb.2007.09.007 | pmc = 2322878 | pmid = 17905422 }}</ref> Unusually among most psychedelics, DiPT did not show evidence of behavioral tolerance in rodents.<ref name="SmithBaileyWilliams2014">{{cite journal | vauthors = Smith DA, Bailey JM, Williams D, Fantegrossi WE | date = December 2014 | title = Tolerance and cross-tolerance to head twitch behavior elicited by phenethylamine- and tryptamine-derived hallucinogens in mice | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 351 | issue = 3 | pages = 485–491 | doi = 10.1124/jpet.114.219337 | pmc = 4309922 | pmid = 25271256 }}</ref>

==Chemistry== [[File:N,N-Dipropyltryptamine.jpg|alt=DPT HCl Powder|thumb|DPT hydrochloride powder.]]

DPT, also known as ''N'',''N''-dipropyltryptamine, is a substituted tryptamine related to dimethyltryptamine (DMT).<ref name="TiHKAL" /> It is found either as a crystalline hydrochloride salt or as an oily or crystalline base. The drug is synthetic and has not been found to occur endogenously.<ref name="Pinchbeck2003" />

===Detection=== DPT changes Ehrlich's reagent violet and causes the marquis reagent to turn yellow.<ref name="Spratley_2004">{{cite journal | vauthors = Spratley T | date = 2004 | title = Analytical Profiles for Five "Designer" Tryptamines | journal = Microgram Journal | volume = 3 | issue = 1–2 | pages = 55 | url = http://www.erowid.org/library/periodicals/microgram/microgram_journal_2005-1.pdf#page=54 | access-date = 2013-10-09 }}</ref>

===Synthesis=== The chemical synthesis of DPT has been described.<ref name="TiHKAL" />

===Analogues=== Analogues of DPT include dimethyltryptamine (DMT), diethyltryptamine (DET), diisopropyltryptamine (DiPT), diallyltryptamine (DALT), methylethyltryptamine (MET), methylpropyltryptamine (MPT), ethylpropyltryptamine (EPT), propylisopropyltryptamine (PiPT), propylallyltryptamine (PALT), 4-HO-DPT, 5-HO-DPT, and 5-MeO-DPT, among others.<ref name="TiHKAL" />

Cyclized tryptamine and partial ergoline derivatives of DPT include RU-28251 (4,α-methylene-DPT), Bay R 1531 (LY-197206; 4,α-methylene-5-MeO-DPT), LY-293284 (4,α-methylene-5-acetyl-DPT), and LY-178210 (LY-228729; 4,α-methylene-5-carboxamido-DPT).

A positional isomer of DPT with the side chain instead located at the 4 position is DPAI (2-desoxo-2-ene-ropinirole).<ref name="ClemensKornfeldPhebus1982">{{cite book | vauthors = Clemens JA, Kornfeld EC, Phebus LA, Shaar CJ, Smalstig EB, Cassady JM, Nichols DE, Kelly E | date = September 1981 | chapter = Dopaminergic Agents Related to Ergolines. | title = The Chemical Regulation of Biological Mechanisms: The Proceedings of the 1st Medicinal Chemistry Symposium | publisher = Royal Society of Chemistry | volume = 42 | page = 167 | location = Cambridge, England | chapter-url = https://archive.org/details/chemicalregulati0000medi/page/167/mode/1up }}</ref><ref name="Nichols1983">{{cite book | author = David E. Nichols | date = 29 June 1983 | chapter = The Development of Novel Dopamine Agonists | title = Dopamine Receptors | series = ACS Symposium Series | publisher = American Chemical Society | volume = 224 | pages = 201–222 | isbn = 978-0-8412-0781-3 | doi = 10.1021/bk-1983-0224.ch009 | publication-place = Washington, D.C. | chapter-url = https://isomerdesign.com/bitnest/external/10.1021/bk-1983-0224.ch009 }}</ref><ref name="ClemensFullerPhebus1984">{{cite journal | vauthors = Clemens JA, Fuller RW, Phebus LA, Smalstig EB, Hynes MD, Cassady JM, Nichols DE, Kelly E, Persons P | date = March 1984 | title = Stimulation of presynaptic dopamine autoreceptors by 4-(2-di-n-propylaminoethyl) indole (DPAI) | journal = Life Sciences | volume = 34 | issue = 11 | pages = 1015–1022 | doi = 10.1016/0024-3205(84)90014-6 | pmid = 6422174 }}</ref>

==History== DPT was first described in the scientific literature by Speeter and Anthony in 1954.<ref name="Szara1970">{{cite book | author = Stephen Szara | date = 1970 | editor = Daniel H. Efron | chapter = DMT (N,N-Dimethyltryptamine) and Homologues: Clinical and Pharmacological Considerations | title = Psychotomimetic Drugs: Proceedings of a Workshop Organized by the Pharmacology Section, Psychopharmacology Research Branch, National Institute of Mental Health | publisher = Raven Press | pages = 275–286 | isbn = 978-0-911216-07-3 | url = https://books.google.com/books?id=xIA4AQAAIAAJ | location = New York | chapter-url = https://www.samorini.it/doc1/alt_aut/sz/szara-dmt-and-homologues.pdf#page=2 | quote = Speeter and Anthony (1954) reported that N,N-dipropyltryptamine (DPT), another tryptamine derivative, produced observable effects in dogs. The similarity in chemical structure between DPT (Fig. 1) and other hallucinogenic tryptamine derivatives and its reported effects in animals suggested that this compound might be capable of producing hallucinogenic effects in humans. }}</ref><ref name="SpeeterAnthony1954">{{cite journal | vauthors = Speeter ME, Anthony WC | date = 1954 | title = The Action of Oxalyl Chloride on Indoles: A New Approach to Tryptamines | journal = Journal of the American Chemical Society | volume = 76 | issue = 23 | pages = 6208–6210 | doi = 10.1021/ja01652a113 | issn = 0002-7863 }}</ref><ref name="Barlow_1959">{{cite journal | vauthors = Barlow RB, Khan I | date = December 1959 | title = The use of the guinea-pig ileum preparation for testing the activity of substances which imitate or antagonize the actions of 5-hydroxytryptamine and tryptamine | journal = British Journal of Pharmacology and Chemotherapy | volume = 14 | issue = 4 | pages = 553–558 | doi = 10.1111/j.1476-5381.1959.tb00963.x | pmc = 1481908 | pmid = 13796840 }}</ref><ref name="Barlow_1959a">{{cite journal | vauthors = Barlow RB, Khan I | date = June 1959 | title = Actions of some analogues of 5-hydroxytryptamine on the isolated rat uterus and the rat fundus strip preparations | journal = British Journal of Pharmacology and Chemotherapy | volume = 14 | issue = 2 | pages = 265–272 | doi = 10.1111/j.1476-5381.1959.tb01397.x | pmc = 1481803 | pmid = 13662587 }}</ref><ref name="Vane_1959">{{cite journal | vauthors = Vane JR | date = March 1959 | title = The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation | journal = British Journal of Pharmacology and Chemotherapy | volume = 14 | issue = 1 | pages = 87–98 | doi = 10.1111/j.1476-5381.1959.tb00933.x | pmc = 1481817 | pmid = 13651584 }}</ref> Use of DPT as a designer drug has been documented by law enforcement officials since as early as 1968.<ref name="Microgram1968">{{cite journal | date = April 1968 | title = Microgram Journal Volume One No. 7 | journal = Microgram Journal | publisher = U.S DOJ, Bureau of Narcotics and Dangerous Drugs | volume = One | issue = Seven | pages = 23 | url = https://www.erowid.org/library/periodicals/microgram/microgram_1968_04_v01n07.pdf | access-date = 5 April 2021 | orig-year = 1968 }}</ref> It was described as a treatment for alcoholism by Stanislav Grof and colleagues in 1973.<ref name="MalacaLoFaroTamborra2020" /><ref name="TittarelliManocchiPantano2015" /><ref name="SoskinGrofRichards1973" /><ref name="Garcia-RomeuKersgaardAddy2016">{{cite journal | vauthors = Garcia-Romeu A, Kersgaard B, Addy PH | date = August 2016 | title = Clinical applications of hallucinogens: A review | journal = Experimental and Clinical Psychopharmacology | volume = 24 | issue = 4 | pages = 229–268 | doi = 10.1037/pha0000084 | pmc = 5001686 | pmid = 27454674 | quote = Like other classic hallucinogens, research with DMT ceased with the passage of the Controlled Substances Act, and was never investigated as an aid in clinical treatment to the extent LSD was. However, research with dipropyltryptamine (DPT), a closely related synthetic analog of DMT, revealed some promise as an adjunct to psychotherapy both with alcoholics (Grof et al., 1973; Rhead et al., 1977; Soskin et al., 1973), and those with anxiety associated with a terminal cancer diagnosis (Richards et al., 1977; 1980; Richards, 1978). }}</ref> The drug was also studied for treatment of anxiety associated with terminal cancer in the late 1970s.<ref name="Garcia-RomeuKersgaardAddy2016" /> However, it was not further studied for such purposes after 1980.<ref name="Garcia-RomeuRichards2018">{{cite journal | vauthors = Garcia-Romeu A, Richards WA | date = August 2018 | title = Current perspectives on psychedelic therapy: use of serotonergic hallucinogens in clinical interventions | journal = International Review of Psychiatry | volume = 30 | issue = 4 | pages = 291–316 | doi = 10.1080/09540261.2018.1486289 | pmid = 30422079 | quote = Others, like N, N-dipropyltryptamine (DPT), have been used in preliminary studies showing therapeutic potential (Grof et al., 1973; Richards, 1978; Richards, Rhead, DiLeo, Yensen, & Kurland, 1977; Richards et al., 1980), but have not been examined since. }}</ref>

==Society and culture== ===Religious use=== DPT is used as a religious sacrament by the Temple of the True Inner Light, a New York City offshoot of the Native American Church.<ref name="TiHKAL" /> The Temple believes DPT and other entheogens are physical manifestations of God.<ref name="TiHKAL" /><ref>{{cite web | title = Temple of the True Inner Light | work = tripod.com | url = http://psychede.tripod.com/ }}</ref>

===Legal status=== ====Canada==== DPT is not a controlled substance in Canada as of 2025.<ref name="CDSA">{{cite web | title = Controlled Drugs and Substances Act | website = Department of Justice Canada | url = https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date = 19 January 2026 }}</ref>

====Sweden==== DPT is illegal in Sweden as of 26 January 2016.<ref>{{cite web | date = November 2015 | title = 31 nya ämnen kan klassas som narkotika eller hälsofarlig vara | language = sv | publisher = Folkhälsomyndigheten | url = http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/november/31-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/ }}</ref>

====United Kingdom==== DPT is a Class A drug in the United Kingdom, making it illegal to possess or distribute.

====United States==== DPT is not scheduled at the federal level in the United States,<ref name="PART 1308 – SCHEDULES OF CONTROLLED SUBSTANCES – 1308.11 Schedule I">{{cite web | title = SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I. | work = CFR | url = http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm | access-date = 17 December 2014 | archive-date = 27 August 2009 | archive-url = https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm | url-status = dead }}</ref> but it could be considered an analog of 5-MeO-DiPT, DMT, or DET, in which case purchase, sale, or possession could be prosecuted under the Federal Analogue Act.

=====Florida===== "DPT (N,N-Dipropyltryptamine)" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.<ref name="Florida Statutes – Chapter 893 – DRUG ABUSE PREVENTION AND CONTROL">[http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html Florida Statutes – Chapter 893 – DRUG ABUSE PREVENTION AND CONTROL]</ref>

=====Maine===== DPT is a Schedule I controlled substance in the state of Maine making it illegal to buy, sell, or possess in Maine.

==Research== === Fragile X syndrome === DPT has been found to completely prevent audiogenic seizures in mouse models of fragile X syndrome (FXS) at a 10{{nbsp}}mg/kg dose, with its mechanism of action appearing to be independent of serotonin and sigma σ₁ receptor activation.<ref name="Tyagi_2023" /> While DPT is an agonist at several serotonin receptors ''in vitro'', its anticonvulsant effects were not blocked by selective serotonin 5-HT_2A, 5-HT_1A, or 5-HT_1B receptor antagonists nor by a selective sigma σ₁ receptor antagonist ''in vivo''.<ref name="Tyagi_2023" /> The drug's beneficial effects may be mediated by non-serotonergic pathways, possibly involving direct auditory processing modulation.<ref name="Tyagi_2023" /> At higher doses, DPT switched from anticonvulsant to proconvulsant action, indicating complex interactions.<ref name="Tyagi_2023" />

== See also == * Substituted tryptamine

== References == {{Reflist}}

== External links == * [https://isomerdesign.com/pihkal/explore/5009 DPT - Isomer Design] * [https://psychonautwiki.org/wiki/DPT DPT - PsychonautWiki] * [https://www.erowid.org/chemicals/dpt/dpt.shtml DPT - Erowid] * [https://www.erowid.org/library/books_online/tihkal/tihkal09.shtml DPT - TiHKAL - Erowid] * [http://isomerdesign.com/PiHKAL/explore.php?domain=tk&id=5009 DPT - TiHKAL - Isomer Design] * [https://www.bluelight.org/xf/threads/59257 The Big & Dandy DPT Thread - Bluelight] * [https://www.erowid.org/chemicals/dpt/dpt_primer.shtml A DPT Primer by Toad - Erowid]

{{Psychedelics}} {{Serotonin receptor modulators}} {{Sigma receptor modulators}} {{Monoamine reuptake inhibitors}} {{Tryptamines}}

Category:5-HT1A agonists Category:5-HT1B agonists Category:5-HT2A agonists Category:5-HT2C agonists Category:Designer drugs Category:N,N-Dialkyltryptamines Category:Dipropylamino compounds Category:Entheogens Category:Psychedelic-assisted therapy Category:Psychedelic tryptamines Category:Serotonin receptor agonists Category:Serotonin reuptake inhibitors Category:Sigma receptor modulators Category:TiHKAL