{{Short description|Class of chemical compounds}} {{Distinguish|scalar}} [[File:Mescaline Structural Formulae bondline.svg|thumb|right|200px|class=skin-invert-image|Mescaline, the most well-known scaline psychedelic.]]
A '''scaline''', also known as a '''substituted mescaline analogue''' and typically but not always a '''4-substituted 3,5-dimethoxyphenethylamine''', is an analogue of the phenethylamine serotonergic psychedelic mescaline (3,4,5-trimethoxyphenethylamine).<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://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6 | access-date=1 February 2025}}</ref><ref name="BraunBraunJacob1978">{{cite journal | vauthors = Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT | title = Mescaline analogs: substitutions at the 4-position | journal = NIDA Res Monogr | volume = | issue = 22 | pages = 27–37 | date = 1978 | pmid = 101882 | doi = | url = https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38 | archive-url = https://web.archive.org/web/20230805004421/https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38 | archive-date = August 5, 2023 }}</ref><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="Shulgin1978">{{cite book | veditors = Iversen LL, Iversen SD, Snyder SH | last=Shulgin | first=Alexander T. | title=Stimulants | chapter=Psychotomimetic Drugs: Structure-Activity Relationships | publisher=Springer US | publication-place=Boston, MA | date=1978 | isbn=978-1-4757-0512-6 | doi=10.1007/978-1-4757-0510-2_6 | pages=243–333 | chapter-url=https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_6 | url=https://books.google.com/books?id=h0_uBwAAQBAJ&pg=PA261 }}</ref><ref name="Shulgin1973">{{cite journal | vauthors = Shulgin AT | title = Mescaline: the chemistry and pharmacology of its analogs | journal = Lloydia | volume = 36 | issue = 1 | pages = 46–58 | date = March 1973 | pmid = 4576313 | doi = | url = https://bitnest.netfirms.com/external/Lloydia/36.1.46}}</ref><ref name="PiHKAL1991">{{cite book | author1 = Alexander T. Shulgin | author2 = Ann Shulgin | title = PiHKAL: A Chemical Love Story | date = 1991 | publisher = Transform Press | edition = 1st | location = Berkeley, CA | isbn = 978-0-9630096-0-9 | oclc = 25627628 | url = https://books.google.com/books?id=O8AdHBGybpcC }}</ref><ref name="ShulginManningDaley2011">{{cite book | vauthors = Shulgin A, Manning T, Daley PF | title = The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds | publisher = Transform Press | location = Berkeley, CA | volume = 1 | year = 2011 | isbn = 978-0-9630096-3-0 | oclc = 709667010 }}</ref>
Other related compounds include the 2C (4-substituted 2,5-dimethoxyphenethylamine) and DOx (4-substituted 2,5-dimethoxyamphetamine) compounds as well as 3,4,5-trimethoxyamphetamine (TMA) and other 4-substituted 3,5-dimethoxyamphetamines (3C drugs).<ref name="Shulgin2003" /><ref name="BraunBraunJacob1978" /><ref name="JacobShulgin1994" /><ref name="Shulgin1978" /> They are also mescaline analogues, but the 2C and DOx drugs have a methoxy group at the 2 position instead of the 3 position of the phenyl ring, while TMA is an amphetamine rather than a phenethylamine.<ref name="Shulgin2003" /><ref name="BraunBraunJacob1978" /><ref name="JacobShulgin1994" /><ref name="Shulgin1978" />
The pharmacology of mescaline analogues has been studied.<ref name="KolaczynskaLuethiTrachsel2021">{{cite journal | vauthors = Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME | title = Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines | journal = Front Pharmacol | volume = 12 | issue = | article-number = 794254 | date = 2021 | pmid = 35222010 | pmc = 8865417 | doi = 10.3389/fphar.2021.794254 | doi-access = free | url = }}</ref><ref name="HalberstadtChathaChapman2019">{{cite journal | vauthors = Halberstadt AL, Chatha M, Chapman SJ, Brandt SD | title = Comparison of the behavioral effects of mescaline analogs using the head twitch response in mice | journal = J Psychopharmacol | volume = 33 | issue = 3 | pages = 406–414 | date = March 2019 | pmid = 30789291 | pmc = 6848748 | doi = 10.1177/0269881119826610 | url = }}</ref><ref name="StoeckmannTrachselLiechti2024" /> Mescaline analogues, or 4-substituted 3,5-dimethoxyphenethylamines specifically, tend to be much less potent than the 2C and DOx drugs.<ref name="Shulgin2003" /><ref name="JacobShulgin1994" /><ref name="BraunBraunJacob1978" /> This relates to the fact that the 2,4,5-substitution pattern tends to be optimal in terms of receptor affinity and potency.<ref name="Shulgin2003" /><ref name="DowdHerrick-DavisEgan2000">{{cite journal | vauthors = Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA | title = 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists | journal = Journal of Medicinal Chemistry | volume = 43 | issue = 16 | pages = 3074–3084 | date = August 2000 | pmid = 10956215 | doi = 10.1021/jm9906062 | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=ad45346022bb7e6e1bec1fbfbcca3bcb60b13058 | url-access = subscription }}</ref> However, mescaline analogues are frequently much more potent than mescaline.<ref name="Shulgin2003" /><ref name="JacobShulgin1994" />
Substituted mescaline analogues have been extensively characterized by Alexander Shulgin and described in his books such as ''PiHKAL'' (''Phenethylamines I Have Known and Loved'')<ref name="PiHKAL1991" /> and ''The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds''<ref name="ShulginManningDaley2011" /> as well as in his literature reviews.<ref name="Shulgin2003" /><ref name="JacobShulgin1994" /><ref name="Shulgin1978" /><ref name="Shulgin1973" /> They have also been studied by David E. Nichols<ref name="NicholsDyer1977">{{cite journal | vauthors = Nichols DE, Dyer DC | title = Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues | journal = J Med Chem | volume = 20 | issue = 2 | pages = 299–301 | date = February 1977 | pmid = 836502 | doi = 10.1021/jm00212a022 | url = }}</ref><ref name="MonteWaldmanMarona-Lewicka1997">{{cite journal | vauthors = Monte AP, Waldman SR, Marona-Lewicka D, Wainscott DB, Nelson DL, Sanders-Bush E, Nichols DE | title = Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives | journal = J Med Chem | volume = 40 | issue = 19 | pages = 2997–3008 | date = September 1997 | pmid = 9301661 | doi = 10.1021/jm970219x | url = }}</ref><ref name="McLeanChambersParrish2006">{{cite journal | vauthors = McLean TH, Chambers JJ, Parrish JC, Braden MR, Marona-Lewicka D, Kurrasch-Orbaugh D, Nichols DE | title = C-(4,5,6-trimethoxyindan-1-yl)methanamine: a mescaline analogue designed using a homology model of the 5-HT2A receptor | journal = J Med Chem | volume = 49 | issue = 14 | pages = 4269–4274 | date = July 2006 | pmid = 16821786 | doi = 10.1021/jm060272y | url = }}</ref> and Daniel Trachsel,<ref name="TrachselLehmannEnzensperger2013">{{cite book | last1=Trachsel | first1=D. | last2=Lehmann | first2=D. | last3=Enzensperger | first3=C. | title=Phenethylamine: von der Struktur zur Funktion | trans-title = Phenethylamines: From Structure to Function | edition = 1 | publisher=Nachtschatten-Verlag | location = Solothurn | series=Nachtschatten-Science | year=2013 | isbn=978-3-03788-700-4 | oclc = 858805226 | url=https://books.google.com/books?id=-Us1kgEACAAJ | language=de | access-date=31 January 2025 }}</ref><ref name="KolaczynskaLuethiTrachsel2021" /><ref name="StoeckmannTrachselLiechti2024">{{cite journal | vauthors=Stoeckmann OV, Trachsel D, Liechti ME, Rudin D | title=Supplementum 276: Abstracts of the 8th Annual Spring Congress of the Swiss Society of General Internal Medicine: P181. New Mescaline Derivatives: Profiling of Scalines' Potency and Affinity on Different Serotonin Receptor Subtypes | journal=Swiss Medical Weekly | volume=154 | issue=5 | date=21 May 2024 | issn=1424-3997 | doi=10.57187/s.3896 | doi-access=free | pages=138S }}</ref> among other researchers.
A closely related group is '''thioscalines''', which are scalines in which one or more of the alkoxy groups are replaced with alkylthio groups.<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="JacobShulgin1994" /><ref name="ShulginManningDaley2011" /><ref name="TrachselLehmannEnzensperger2013" />
==Use and effects== {{Sticky}} {| class="wikitable sortable sticky-header" |+ {{Nowrap|Doses and durations of scalines}} |- ! Compound !! Chemical name !! Dose !! Duration |- | α,α-Dideuteromescaline (α-D) || 3,4,5-Trimethoxy-α,α-dideuterophenethylamine || 230 mg || Unknown |- | α,β-Dideuteromescaline (α,β-D) || 3,4,5-Trimethoxy-α,β-dideuterophenethylamine || 250 mg || Unknown |- | β,β-Dideuteromescaline (β-D) || 3,4,5-Trimethoxy-β,β-dideuterophenethylamine || 200–400 mg || 12 hours |- | 4-Desoxymescaline (DESOXY) || 4-Methyl-3,5-dimethoxyphenethylamine || 40–120 mg || 6–8 hours |- | 4-''O''-Desmethylmescaline (DESMETHYL) || 4-Hydroxy-3,5-dimethoxyphenethylamine || Unknown || Unknown |- | 4-Trideuteromescaline (4-D) || 4-Trideuteromethoxy-3,5-dimethoxyphenethylamine || 200–400 mg || 12 hours |- | Allylescaline (AL) || 4-Allyloxy-3,5-dimethoxyphenethylamine || 20–35 mg || 8–12 hours |- | Asymbescaline (ASB) || 3,4-Diethoxy-5-methoxyphenethylamine || 200–280 mg || 10–15 hours |- | Benzscaline (BZ) || 4-Benzyloxy-3,5-dimethoxyphenethylamine || Unknown || Unknown |- | Biscaline (BI) || 4-Phenyl-3,5-dimethoxyphenethylamine || Unknown || Unknown |- | Buscaline (B) || 4-Butoxy-3,5-dimethoxyphenethylamine || >150 mg || Several hours |- | Cyclopropylmescaline (CPM) || 4-Cyclopropylmethoxy-3,5-dimethoxyphenethylamine || 60–80 mg || 12–18 hours |- | Cycloproscaline (CP) || 4-Cyclopropoxy-3,5-dimethoxyphenethylamine || ≥60 mg || ≥6 hours |- | Difluoroescaline (DFE) || 4-(2,2-Difluoroethoxy)-3,5-dimethoxyphenethylamine || 40–80 mg || 6–12 hours |- | Difluoroisoproscaline (DFIP) || 4-(1,3-Difluoroisopropoxy)-3,5-dimethoxyphenethylamine || Unknown || Unknown |- | Difluoromescaline (DFM) || 4-Difluoromethoxy-3,5-dimethoxyphenethylamine || 50–100 mg || 12–18 hours |- | Escaline (E) || 4-Ethoxy-3,5-dimethoxyphenethylamine || 40–60 mg || 8–12 hours |- | Fluoroescaline (FE) || 4-(2-Fluoroethoxy)-3,5-dimethoxyphenethylamine || ≥75 mg || ~6 hours |- | Fluoroisoproscaline (FIP) || 4-(1-Fluoroisopropoxy)-3,5-dimethoxyphenethylamine || Unknown || Unknown |- | Fluoromescaline (FM) || 4-Fluoromethoxy-3,5-dimethoxyphenethylamine || Unknown || Unknown |- | Fluoroproscaline (FP) || 4-(3-Fluoropropoxy)-3,5-dimethoxyphenethylamine || 60–150 mg || 3–5 hours |- | Isobuscaline (IB) || 4-Isobutoxy-3,5-dimethoxyphenethylamine || 60–100 mg || 10–14 hours |- | Isomescaline (IM) || 2,3,4-Trimethoxyphenethylamine || >400 mg || Unknown |- | Isoproscaline (IP) || 4-Isopropoxy-3,5-dimethoxyphenethylamine || 40–80 mg || 10–16 hours |- | Mescaline (M) || 3,4,5-Trimethoxyphenethylamine || 200–400 (50–800) mg || 10–12 (6–14) hours |- | Metadifluoromescaline (MDFM) || 3-(Difluoromethoxy)-4,5-dimethoxyphenylethylamine || ≥85 mg || ~8 hours |- | Metatrifluoromescaline (MTFM) || 3,4-Dimethoxy-5-(trifluoromethoxy)phenethylamine || Unknown || Unknown |- | Metaescaline (ME) || 3-Ethoxy-4,5-dimethoxyphenethylamine || 200–350 mg || 8–12 hours |- | Metaproscaline (MP) || 3,4-Dimethoxy-5-propoxyphenethylamine || >240 mg || Unknown |- | Methallylescaline (MAL) || 4-Methallyloxy-3,5-dimethoxyphenethylamine || 40–65 mg || 12–16 hours |- | Phenescaline (PE) || 4-Phenethyloxy-3,5-dimethoxyphenethylamine || >150 mg || Unknown |- | Phescaline (PH) || 4-Phenoxy-3,5-dimethoxyphenethylamine || Unknown || Unknown |- | Propynylscaline || 4-Propynyloxy-3,5-dimethoxyphenethylamine || ≥80 mg || 8–12 hours |- | Proscaline (P) || 4-Propoxy-3,5-dimethoxyphenethylamine || 30–60 mg || 8–12 hours |- | ''sec''-Buscaline (SBU) || 4-''sec''-Butoxy-3,5-dimethoxyphenethylamine || Unknown || Unknown |- | Symbescaline (SB) || 4-Methoxy-3,5-diethoxyphenethylamine || >240 mg || Unknown |- | ''tert''-Buscaline (TBU) || 4-''tert''-Butoxy-3,5-dimethoxyphenethylamine || Unknown || Unknown |- | Trescaline (TRIS) || 3,4,5-Triethoxyphenethylamine || >240 mg || Unknown |- | Trifluoroescaline (TFE) || 4-(2,2,2-Trifluoroethoxy)-3,5-dimethoxyphenethylamine || 35–65 mg || 12–18 hours |- | Trifluoroisoproscaline (TFIP) || 4-(1,1,1-Trifluoroisopropoxy)-3,5-dimethoxyphenethylamine || Unknown || Unknown |- | Trifluoromescaline (TFM) || 4-(Trifluoromethoxy)-3,5-dimethoxyphenethylamine || 15–40 mg || 14–24 hours |- | Trifluoroproscaline (TFP) || 4-(3,3,3-Trifluoropropoxy)-3,5-dimethoxyphenethylamine || ≥60 mg || Unknown |- | Viscaline (V) || 4-Vinyl-3,5-dimethoxyphenethylamine || Unknown || Unknown |- |- class="sortbottom" | colspan="5" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Refs:''' <ref name="Shulgin2003" /><ref name="JacobShulgin1994" /><ref name="PiHKAL">{{CitePiHKAL}}</ref><ref name="ShulginManningDaley2011" /><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}}</ref><ref name="Trachsel2012">{{cite journal | vauthors = Trachsel D | title = Fluorine in psychedelic phenethylamines | journal = Drug Test Anal | volume = 4 | issue = 7–8 | pages = 577–590 | date = 2012 | pmid = 22374819 | doi = 10.1002/dta.413 | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=c7b41be36b1f580a264a752521d151e6e2d9409d| url-access = subscription }}</ref><ref name="TrachselLehmannEnzensperger2013" /><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 | doi = 10.1093/ijnp/pyy047 | url = | pmc = 6165951 }}</ref><ref name="KolaczynskaLuethiTrachsel2021" /> |}
{{Sticky}} {| class="wikitable sortable sticky-header" |+ {{Nowrap|Doses and durations of thioscalines}} |- ! Compound !! Chemical name !! Dose !! Duration |- | 3-Thioasymbescaline (3-TASB) || 3-Ethylthio-4-ethoxy-5-methoxyphenethylamine || ~160 mg || 10–18 hours |- | 4-Thioasymbescaline (4-TASB) || 3-Ethoxy-4-ethylthio-5-methoxyphenethylamine || 60–100 mg || 10–15 hours |- | 5-Thioasymbescaline (5-TASB) || 3,4-Diethoxy-5-methylthiophenethylamine || ~160 mg || ~8 hours |- | 4-Thiobuscaline (4-TB) || 4-Butylthio-3,5-dimethoxyphenethylamine || 60–120 mg || ~8 hours |- | 3-Thioescaline (3-TE) || 3-Methylthio-4-ethoxy-5-methoxyphenethylamine || 60–80 mg || 8–12 hours |- | 4-Thioescaline (4-TE) || 4-Ethylthio-3,5-dimethoxyphenethylamine || 20–30 mg || 9–12 hours |- | 2-Thioisomescaline (2-TIM) || 2-Methylthio-3,4-dimethoxyphenethylamine || >240 mg || Unknown |- | 3-Thioisomescaline (3-TIM) || 3-Methylthio-2,4-dimethoxyphenethylamine || >240 mg || Unknown |- | 4-Thioisomescaline (4-TIM) || 4-Methylthio-2,3-dimethoxyphenethylamine || >240 mg || Unknown |- | 3-Thiomescaline (3-TM) || 3-Methylthio-4,5-dimethoxyphenethylamine || 60–100 mg || 8–12 hours |- | 4-Thiomescaline (4-TM) || 4-Methylthio-3,5-dimethoxyphenethylamine || 20–40 mg || 10–15 hours |- | 3-Thiometaescaline (3-TME) || 3-ethylthio-4,5-dimethoxyphenethylamine || 60–100 mg || 10–15 hours |- | 4-Thiometaescaline (4-TME) || 3-Ethoxy-4-methylthio-5-methoxyphenethylamine || 60–100 mg || 10–15 hours |- | 5-Thiometaescaline (5-TME) || 3-Ethoxy-4-methoxy-5-methylthiophenethylamine || >200 mg || Unknown |- | 4-Thioproscaline (4-TP) || 4-Propylthio-3,5-dimethoxyphenethylamine || 20–25 mg || 10–15 hours |- | 3-Thiosymbescaline (3-TSB) || 3-Ethoxy-5-ethylthio-4-methoxyphenethylamine || >200 mg || Unknown |- | 4-Thiosymbescaline (4-TSB) || 4-Methylthio-3,5-diethoxyphenethylamine || >240 mg || Unknown |- | 3-Thiotrescaline (3-T-TRIS) || 3-Ethylthio-4,5-Diethoxyphenethylamine || >160 mg || Unknown |- | 4-Thiotrescaline (4-T-TRIS) || 4-Ethylthio-3,5-diethoxyphenethylamine || >200 mg || Unknown |- |- class="sortbottom" | colspan="5" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Refs:''' <ref name="Shulgin2003" /><ref name="JacobShulgin1994" /><ref name="PiHKAL">{{CitePiHKAL}}</ref><ref name="ShulginManningDaley2011" /><ref name="TrachselLehmannEnzensperger2013" /> |}
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Pharmacology== ===Pharmacodynamics=== {{Sticky}} {| class="wikitable sticky-header" |+ {{Nowrap|Serotonin receptor affinities (K<sub>i</sub>, nM) of selected scalines (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<sub>1A</sub> !! 5-HT<sub>1B</sub> !! 5-HT<sub>1D</sub> !! 5-HT<sub>1E</sub> !! 5-HT<sub>2A</sub> !! 5-HT<sub>2B</sub> !! 5-HT<sub>2C</sub> !! 5-HT<sub>3</sub> !! 5-HT<sub>5A</sub> !! 5-HT<sub>6</sub> !! 5-HT<sub>7</sub> |- | Mescaline || – || – || 794 || – || 1,950 || 398 || – || – || – || – || – |- | Escaline || – || – || 724 || – || – || 148 || 1,950 || – || – || – || – |- | Isoproscaline || – || – || 4,790 || – || 2,750 || 263 || 2,510 || – || – || – || – |- | Cyclopropylmescaline || – || – || – || – || – || 234 || 955 || – || – || – || – |- | Allylescaline || – || – || – || 490 || 2,450 || 245 || 1,320 || – || – || – || – |- | Methallylescaline || – || – || 2,750 || – || 955 || 110 || 324 || – || – || – || – |- |}
==Society and culture== ===Legal status=== ====Canada==== Mescaline and 3,4,5-trimethoxyamphetamine (TMA) are the only scalines (and derivatives) that are controlled substances 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>
==List of scalines== ===4-Substituted=== ====4-Alkoxy-substituted==== * 4-Methoxyescaline (4-MeO-E; MeOEtO) (3,5-dimethoxy-4-(2-methoxyethoxy)phenethylamine) * Allylescaline (AL) (4-allyloxy-3,5-dimethoxyphenethylamine) * Amylescaline (4-''n''-amyloxy-3,5-dimethoxyphenethylamine) * Benzscaline (BZ) (4-benzyloxy-3,5-dimethoxyphenethylamine) * Buscaline (B) (4-butoxy-3,5-dimethoxyphenethylamine) * Cyclopropylmescaline (CPM) (4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine) * Cycloproscaline (CP) (4-cyclopropoxy-3,5-dimethoxyphenethylamine) * Difluoroescaline (DFE) (multiple forms) * Difluoroisoproscaline (DFIP) (multiple forms) * Difluoromescaline (DFM) (4-difluoromethoxy-3,5-dimethoxyphenethylamine) * Escaline (E) (4-ethoxy-3,5-dimethoxyphenethylamine) * Fluoroescaline (FE) (multiple forms) * Fluoromescaline (FM) (4-fluoromethoxy-3,5-dimethoxyphenethylamine) * Fluoroproscaline (FP) (multiple forms) * Hexylescaline (4-''n''-hexyloxy-3,5-dimethoxyphenethylamine) * Isobuscaline (IB) (4-isobutoxy-3,5-dimethoxyphenethylamine) * Isoproscaline (IP) (4-isopropoxy-3,5-dimethoxyphenethylamine) * Methallylescaline (MAL) (4-methylallyloxy-3,5-dimethoxyphenethylamine) * Phenescaline (4-phenylethoxy-3,5-dimethoxyphenethylamine) * Phescaline (4-phenoxy-3,5-dimethoxyphenethylamine) * Propynylscaline (4-propynyloxy-3,5-dimethoxyphenethylamine) * Proscaline (P) (4-propoxy-3,5-dimethoxyphenethylamine) * Septylescaline (4-''n''-heptyloxy-3,5-dimethoxyphenethylamine) * Trifluoroescaline (TFE) (multiple forms) * Trifluoromescaline (TFM) (4-trifluoromethoxy-3,5-dimethoxyphenethylamine) * Trifluoroproscaline (TFP) (multiple forms) * Viscaline (4-vinyl-3,5-dimethoxyphenethylamine)
====4-Alkylthio-substituted==== * 4-Thiobuscaline (4-TB) (4-butylthio-3,5-dimethoxyphenethylamine) * 4-Thioescaline (4-TE) (4-ethylthio-3,5-dimethoxyphenethylamine) * 4-Thiomescaline (4-TM) (4-methylthio-3,5-dimethoxyphenethylamine) * 4-Thioproscaline (4-TP) (4-propylthio-3,5-dimethoxyphenethylamine)
====Others==== * Biscaline (4-phenyl-3,5-dimethoxyphenethylamine) * 4-Bromomescaline (4-Br-3,5-DMPEA) (4-bromo-3,5-dimethoxyphenethylamine) * 4-Desmethylmescaline (desmethyl) (4-hydroxy-3,5-dimethoxyphenethylamine) * 4-Desoxymescaline (desoxy) (4-methyl-3,5-dimethoxyphenethylamine)
===3- or 5-Extended=== {{See also|TWEETIO#Scalines}}
* Asymbescaline (ASB) (3,4-diethoxy-5-methoxyphenethylamine) * Metadifluoromescaline (MDFM) (3,4-dimethoxy-5-difluoromethoxyphenethylamine) * Metaescaline (ME) (3-ethoxy-4,5-dimethoxyphenethylamine) * Metaproscaline (MP) (3,4-dimethoxy-5-propoxyphenethylamine) * Symbescaline (SB) (4-methoxy-3,5-diethoxyphenethylamine) * 4-Thioasymbescaline (4-TASB) (4-ethylthio-3-ethoxy-5-methoxyphenethylamine) * 4-Thiometaescaline (4-TME) (4-methylthio-3-ethoxy-5-methoxyphenethylamine) * 4-Thiosymbescaline (4-TSB) (4-methylthio-3,5-diethoxyphenethylamine) * 4-Thiotrescaline (4-T-TRIS; 4-thiotrisescaline) (4-ethylthio-3,5-diethoxyphenethylamine) * Trescaline (TRIS; trisescaline) (3,4,5-triethoxyphenethylamine)
===3- or 5-Replaced=== * 3-Desmethylmescaline (3-DESMETHYL) (3,4-dimethoxy-5-hydroxyphenethylamine) * 3-Thioasymbescaline (3-TASB) (3-ethylthio-4-ethoxy-5-methoxyphenethylamine) * 5-Thioasymbescaline (5-TASB) (3,4-diethoxy-5-methylthiophenethylamine) * 3-Thioescaline (3-TE) (3-methoxy-4-ethoxy-5-methylthiophenethylamine) * 3-Thiomescaline (3-TM) (3,4-dimethoxy-5-methylthiophenethylamine) * 3-Thiometaescaline (3-TME) (3-ethylthio-4,5-dimethoxyphenethylamine) * 5-Thiometaescaline (5-TME) (3-ethoxy-4-methoxy-5-methylthiophenethylamine) * 3-Thiosymbescaline (3-TSB) (3-ethoxy-4-methoxy-5-ethylthiophenethylamine) * 3-Thiotrescaline (3-T-TRIS; 3-thiotrisescaline) (3,4-diethoxy-5-ethylthiophenethylamine) * 3,4,5-Trideoxymescaline (TMePEA) (3,4,5-trimethylphenethylamine)
===2- or 6-Substituted=== * 2-Bromo-6-chloromescaline (2-bromo-6-chloro-3,4,5-trimethoxyphenethylamine) * 2-Bromo-6-methylmescaline (2-bromo-6-methyl-3,4,5-trimethoxyphenethylamine) * 2-Bromomescaline (2-bromo-3,4,5-trimethoxyphenethylamine) * 2-Chloromescaline (2-chloro-3,4,5-trimethoxyphenethylamine) * 2-Iodomescaline (2-iodo-3,4,5-trimethoxyphenethylamine) * 2-Methylmescaline (2-methyl-3,4,5-trimethoxyphenethylamine) * 2,6-Dibromomescaline (2,6-dibromo-3,4,5-trimethoxyphenethylamine) * 2,6-Dichloromescaline (2,6-dichloro-3,4,5-trimethoxyphenethylamine) * 2,6-Dimethylmescaline (2,6-dimethyl-3,4,5-trimethoxyphenethylamine) * 2,3,4,5,6-Pentamethoxyphenethylamine (PeMPEA; 2,6-dimethoxymescaline) * 2,3,4,5-Tetramethoxyphenethylamine (TeMPEA; TeMPEA-1; 2-methoxymescaline)
===''N''-Substituted=== * ''N''-Acetylmescaline (''N''-acetyl-3,4,5-trimethoxyphenethylamine) * ''N''-Formylmescaline (''N''-formyl-3,4,5-trimethoxyphenethylamine) * ''N'',''N''-Diformylmescaline (''N'',''N''-diformyl-3,4,5-trimethoxyphenethylamine) * ''N''-Methylmescaline (M-M) (''N''-methyl-3,4,5-trimethoxyphenethylamine) * M-NDEPA (''N''-diethylaminocarbonylethyl-3,4,5-trimethoxyamphetamine) * NBOMe-escaline (''N''-(2-methoxybenzyl)-4-ethoxy-3,5-dimethoxyphenethylamine) * NBOMe-mescaline (''N''-(2-methoxybenzyl)-3,4,5-trimethoxyphenethylamine) * Trichocereine (MM-M) (''N'',''N''-dimethylmescaline; ''N'',''N''-dimethyl-3,4,5-trimethoxyphenethylamine)
===α- or β-Substituted=== {{See also|3C (psychedelics)|BOx (psychedelics)}}
* BOM (β,3,4,5-tetramethoxyphenethylamine; β-methoxymescaline) * α-Ethylmescaline (AEM) (α-ethyl-3,4,5-trimethoxyphenethylamine) * β-HOM (3,4,5-trimethoxy-β-hydroxyphenethylamine; β-hydroxymescaline; mescalol) * 3,4,5-Trimethoxyamphetamine (3,4,5-TMA; TMA; TMA-1; α-methylmescaline)
===Cyclized=== * Bromojimscaline (1-(7-bromo-4,5,6-trimethoxy-2,3-dihydro-1''H''-inden-1-yl)methanamine) * Bromotomscaline (1-(5-bromo-2,3,4-trimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine) * DEMPDHPCA-M (DEMPDHPCA-mescaline; ''N'',''N''-diethyl-1-methyl-5-(3,4,5-trimethoxyphenyl)-1,2,3,6-tetrahydropyridine-3-carboxamide) * Flyscaline (mescaline-FLY) * Jimscaline (1-(4,5,6-trimethoxy-2,3-dihydro-1''H''-inden-1-yl)methylamine) * Tomscaline (1-(2,3,4-trimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine)
===Deuterated=== {{See also|Deumescaline}}
* 2,6-D (2,6-dideuteromescaline; 2,6-dideutero-3,4,5-trimethoxyphenethylamine) * 3,5-D (3,5-di(trideutero)mescaline; 4-methoxy-3,5-di(trideuteromethoxy)phenethylamine) * 4-D (4-trideuteromescaline; 4-trideuteromethoxy-3,5-methoxyphenethylamine) * Alpha-D (α-D; 3,4,5-trimethoxy-α,α-dideuterophenethylamine; α,α-dideuteromescaline) * Alpha,Beta-D (α,β-D; 3,4,5-trimethoxy-α,β-dideuterophenethylamine; α,β-dideuteromescaline) * Beta-D (β-D; 3,4,5-trimethoxy-β,β-dideuterophenethylamine; β,β-dideuteromescaline)
===Other compounds=== * 3-Methoxy-4,5-dihydroxyphenethylamine (4-''O''-,5-''O''-didesmethylmescaline) * 3,5-Dimethoxyphenethylamine (3,5-DMPEA; 4-desmethoxymescaline) * Isomescaline (IM) (2,3,4-trimethoxyphenethylamine) * Lophophine (2C-MMDA; 5-methoxy-MDPEA; MMDPEA; 3-methoxy-4,5-methylenedioxyphenethylamine) * 2-Thioisomescaline (2-TIM) (2-methylthio-3,4-dimethoxyphenethylamine) * 3-Thioisomescaline (3-TIM) (3-methylthio-2,4-dimethoxyphenethylamine) * 4-Thioisomescaline (4-TIM) (4-methylthio-2,4-dimethoxyphenethylamine)
==Related compounds== * 3,4-Dimethoxyphenethylamine (DMPEA; 3,4-DMPEA; homoveratrylamine; 3-desmethoxymescaline) * 3-Methoxy-4-ethoxyphenethylamine (MEPEA; 3-desmethoxyescaline) * 3-Methoxy-4-allyloxyphenethylamine (MAPEA; 3-desmethoxyallylescaline) * 3-Methoxy-4-propoxyamphetamine (POMA; 3-desmethoxyproscaline)
==See also== * Substituted methoxyphenethylamine * 3C (psychedelics) (4-substituted 3,5-dimethoxyamphetamines) * Desoxyscaline * ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') * ''The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds''
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/home Isomer Design] * [https://pageviews.wmcloud.org/massviews/?platform=all-access&agent=user&source=category&range=latest-365&subjectpage=0&subcategories=0&sort=views&direction=1&view=list&target=https://en.wikipedia.org/wiki/Category:Scalines Scalines - Wikipedia Massviews Analysis (Wikipedia Page Views of Individual Scalines)]
{{Psychedelics}} {{Phenethylamines}} {{Chemical classes of psychoactive drugs}}
Category:Alexander Shulgin Category:Chemical classes of psychoactive drugs Category:Psychedelic phenethylamines Category:Scalines