# Proscaline

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Proscaline
> Markdown URL: https://mediated.wiki/source/Proscaline.md
> Source: https://en.wikipedia.org/wiki/Proscaline
> Source revision: 1355938365
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{{Infobox drug
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 464217897
| drug_name = 
| image = Proscaline.svg
| image_class = skin-invert-image
| width = 250px
| caption = 
| image2 = Proscaline 3D.png
| image_class2 = bg-transparent
| width2 = 200px

<!-- Clinical data -->
| pronounce = 
| tradename = 
| Drugs.com = 
| MedlinePlus = 
| licence_CA = 
| licence_EU = 
| DailyMedID = 
| licence_US = 
| pregnancy_AU = 
| pregnancy_category = 
| dependency_liability = 
| addiction_liability = 
| routes_of_administration = [Oral](/source/Oral_administration)<ref name="PiHKAL" />
| class = [Serotonin](/source/Serotonin) [5-HT<sub>2</sub> receptor](/source/5-HT2_receptor) [agonist](/source/agonist); [Serotonergic psychedelic](/source/Serotonergic_psychedelic); [Hallucinogen](/source/Hallucinogen)
| ATC_prefix = None
| ATC_suffix = 

<!-- Legal status -->
| legal_status = 

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = 
| metabolites = 
| onset = 
| elimination_half-life = 
| duration_of_action = 8–12 hours<ref name="PiHKAL" />
| excretion = 

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|EPA}}
| CAS_number = 39201-78-0
| CAS_supplemental = 
| PubChem = 15102790
| PubChemSubstance = 
| IUPHAR_ligand = 
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10439596
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 99G781N5IO
| KEGG = 
| ChEBI = 
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 340765
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = 4-Propoxy-3,5-dimethoxyphenethylamine; 4-Propoxy-3,5-DMPEA

<!-- Chemical data -->
| IUPAC_name = 2-(3,5-dimethoxy-4-propoxyphenyl)ethan-1-amine
| C=13 | H=21 | N=1 | O=3
| SMILES = COc1cc(cc(OC)c1OCCC)CCN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H21NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h8-9H,4-7,14H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HYWLMSUAZVDUFW-UHFFFAOYSA-N
}}

'''Proscaline''', also known as '''4-propoxy-3,5-dimethoxyphenethylamine''', is a [psychedelic drug](/source/psychedelic_drug) of the [phenethylamine](/source/substituted_phenethylamine) and [scaline](/source/scaline) families related to [mescaline](/source/mescaline).<ref name="PiHKAL" /> It is taken [orally](/source/oral_administration).<ref name="PiHKAL" /><ref name="HalberstadtChathaKlein2020" />

==Use and effects==
In his book ''[PiHKAL](/source/PiHKAL)'' (''Phenethylamines I Have Known and Loved'') and other publications, [Alexander Shulgin](/source/Alexander_Shulgin) reports that a dose of 30 to 60{{nbsp}}mg [orally](/source/oral_administration) produces effects lasting 8 to 12{{nbsp}}hours.<ref name="PiHKAL">[http://www.erowid.org/library/books_online/pihkal/pihkal140.shtml Proscaline entry in PiHKAL]</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://bitnest.netfirms.com/external/Books/NIDA146.74}}</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="HalberstadtChathaKlein2020">{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD | 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 | issue = | article-number = 107933 | date = May 2020 | pmid = 31917152 | pmc = 9191653 | doi = 10.1016/j.neuropharm.2019.107933 | url = http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf | quote = Table 4 Human potency data for selected hallucinogens. [...] }}</ref> The [onset](/source/onset_of_action) was not described, but peak effects occurred after about 2{{nbsp}}hours.<ref name="PiHKAL" /> A typical dose estimate is 45{{nbsp}}mg.<ref name="HalberstadtChathaKlein2020" /> Doses as high as 80{{nbsp}}mg have also been explored.<ref name="PiHKAL" /> The drug has approximately 6 or 7{{nbsp}}times the [potency](/source/potency_(pharmacology)) of mescaline, which itself has a listed dose range of 200 to 400{{nbsp}}mg.<ref name="PiHKAL" /><ref name="JacobShulgin1994" /><ref name="Shulgin2003" /><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="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>

The effects of proscaline have been reported to include insignificant [closed-eye visual](/source/closed-eye_visual)s, sharpening of the [sense](/source/sense)s, [hyperawareness](/source/hyperawareness), [relaxation](/source/mental_relaxation) and feeling at ease, deep feelings of peace and contentment, [euphoria](/source/euphoria), no enhanced clarity or deep realizations, feelings of uninhibited [eroticism](/source/eroticism), [pain relief](/source/pain_relief), [drowsiness](/source/drowsiness), [intoxication](/source/drug_intoxication) and [feeling drunk](/source/drunkenness), [irritability](/source/irritability), [restlessness](/source/psychomotor_agitation), [tremor](/source/tremor)s, [insomnia](/source/insomnia), difficulty with [dream](/source/dream)s, long-lasting residual effects, and no next-day [hangover](/source/hangover).<ref name="PiHKAL" />

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

==Pharmacology==
===Pharmacodynamics===
Proscaline is a [serotonin](/source/serotonin) [5-HT<sub>2</sub> receptor](/source/5-HT2_receptor) [agonist](/source/agonist), including of the serotonin [5-HT<sub>2A</sub>](/source/5-HT2A_receptor), [5-HT<sub>2B</sub>](/source/5-HT2B_receptor), and [5-HT<sub>2C</sub> receptor](/source/5-HT2C_receptor)s.<ref name="WallachCaoCalkins2023">{{cite journal | vauthors = Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD | title = Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential | journal = Nat Commun | volume = 14 | issue = 1 | article-number = 8221 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 | bibcode = 2023NatCo..14.8221W }}</ref><ref name="McCorvy_2013">{{cite thesis | vauthors = McCorvy JD | title = Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics | date = 16 January 2013 | degree = Ph.D. | publisher = Purdue University | via = Purdue e-Pubs | url = https://docs.lib.purdue.edu/dissertations/AAI3545320/ | archive-url = https://web.archive.org/web/20250515110801/https://docs.lib.purdue.edu/dissertations/AAI3545320/ | archive-date = 15 May 2025 | access-date = 27 May 2025 | url-status = bot: unknown }}</ref> Activation of the serotonin 5-HT<sub>2A</sub> receptor is thought to be responsible for its [psychedelic](/source/psychedelic_drug) effects.<ref name="WallachCaoCalkins2023" /> The drug is much more [potent](/source/potency_(pharmacology)) as an agonist of the serotonin 5-HT<sub>2C</sub> receptor than as an agonist of the serotonin 5-HT<sub>2A</sub> or 5-HT<sub>2B</sub> receptors.<ref name="WallachCaoCalkins2023" />

It produces the [head-twitch response](/source/head-twitch_response), a behavioral proxy of psychedelic effects, in rodents.<ref name="WallachCaoCalkins2023" /><ref name="HalberstadtChathaChapman2019" /><ref name="HalberstadtChathaKlein2020" />

==Chemistry==
Proscaline, also known as 4-propoxy-3,5-dimethoxyphenethylamine, is a [substituted phenethylamine](/source/substituted_phenethylamine) and [scaline](/source/scaline) (4-substituted 3,5-dimethoxyphenethylamine) [derivative](/source/chemical_derivative) related to [mescaline](/source/mescaline) (3,4,5-trimethoxyphenethylamine).<ref name="PiHKAL" /> It is the 4-[propoxy](/source/propoxy) [homologue](/source/structural_homolog) of mescaline.<ref name="PiHKAL" />

===Properties===
Proscaline is much more [lipophilic](/source/lipophilic) than [mescaline](/source/mescaline) or [escaline](/source/escaline) ([log P](/source/partition_coefficient) = 1.70, 0.78, and 1.11, respectively), which is expected to be more optimal and advantageous in terms of [drug](/source/drug)-like properties such as [blood–brain barrier](/source/blood%E2%80%93brain_barrier) [permeability](/source/drug_permeability).<ref name="HalberstadtChathaChapman2019" />

===Synthesis===
The [chemical synthesis](/source/chemical_synthesis) of proscaline has been described.<ref name="PiHKAL" />

===Analogues===
[Analogue](/source/Structural_analog)s of proscaline include [mescaline](/source/mescaline), [escaline](/source/escaline), [isoproscaline](/source/isoproscaline), [allylescaline](/source/allylescaline), [methallylescaline](/source/methallylescaline), [propynyl](/source/propynyl_(drug)), [cyclopropylmescaline](/source/cyclopropylmescaline), [cycloproscaline](/source/cycloproscaline), [fluoroproscaline](/source/fluoroproscaline), and [3C-P](/source/3C-P), among others.<ref name="PiHKAL" /><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 = }}</ref><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>

==History==
Proscaline was first [synthesized](/source/chemical_synthesis) and studied by [Otakar Leminger](/source/Otakar_Leminger) in 1972.<ref name="Leminger1972">{{cite journal | author = Otakar Leminger | title = Příspěvek k chemii v jádře alkoxylovaných β-fenoetylaminů – II: O některých v jádře alkoxylovaných β-fenoetylaminech, resp. jejich sulfátech | trans-title = A Contribution to the chemistry of alkoxylated phenethylamines – part 2: On some core-alkoxylated β-phenethylamines and their sulfates | journal = Chemický Průmysl | volume = 22 | issue = | date = 1972 | page = 553–557 | url = https://isomerdesign.com/bitnest/external/ChemickyPrumysl/22.553 | archive-url = https://www.erowid.org/archive/rhodium/chemistry/leminger.html | archive-date = 17 February 2026}}</ref><ref name="PiHKAL" /> The drug was later synthesized by [Alexander Shulgin](/source/Alexander_Shulgin) and further described in his 1991 book ''[PiHKAL](/source/PiHKAL)'' (''Phenethylamines I Have Known and Loved'').<ref name="PiHKAL" /> It was encountered as a novel [designer drug](/source/designer_drug) in [Europe](/source/Europe) in 2013.<ref name="King2014">{{cite journal | vauthors = King LA | title = New phenethylamines in Europe | journal = Drug Test Anal | volume = 6 | issue = 7–8 | pages = 808–818 | date = 2014 | pmid = 24574327 | doi = 10.1002/dta.1570 | url = }}</ref><ref name="EMCDDA2013">https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2013</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>

==Society and culture==
===Legal status===
====Canada====
Proscaline is not a [controlled substance](/source/controlled_substance) in [Canada](/source/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>

====United Kingdom====
Proscaline is a [Class A](/source/Drugs_controlled_by_the_UK_Misuse_of_Drugs_Act) controlled substance in the [United Kingdom](/source/United_Kingdom).{{Citation needed|date=October 2025}}

====United States====
Proscaline is not an explicitly [controlled substance](/source/controlled_substance) in the [United States](/source/United_States).<ref name="OrangeBook2026">{{citation | title = Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) | date = January 2026 | publisher = U.S. [Department of Justice](/source/Department_of_Justice): [Drug Enforcement Administration](/source/Drug_Enforcement_Administration) (DEA): Diversion Control Division | location = [United States](/source/United_States) | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf}}</ref> However, it could be considered a [controlled substance](/source/controlled_substance) under the [Federal Analogue Act](/source/Federal_Analogue_Act) if intended for human consumption.

==See also==
* [Scaline](/source/Scaline)

==References==
{{Reflist}}

==External links==
* [https://isomerdesign.com/pihkal/explore/140 Proscaline - Isomer Design]
* [https://psychonautwiki.org/wiki/Proscaline Proscaline - PsychonautWiki]
* [https://erowid.org/library/books_online/pihkal/pihkal140.shtml P (Proscaline) - PiHKAL - Erowid]
* [https://isomerdesign.com/pihkal/read/pk/140 P (Proscaline) - PiHKAL - Isomer Design]
* [https://www.bluelight.org/xf/threads/392410 The Big & Dandy Proscaline Thread - Bluelight]
* [https://isomerdesign.com/countyourculture/2012/05/04/leminger-allylescaline/ Leminger's Scalines - countyourculture]

{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Phenethylamines}}

Category:5-HT2A agonists
Category:5-HT2B agonists
Category:5-HT2C agonists
Category:Designer drugs
Category:Methoxy compounds
Category:Phenol ethers
Category:PiHKAL
Category:Propoxy compounds
Category:Psychedelic phenethylamines
Category:Scalines

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Adapted from the Wikipedia article [Proscaline](https://en.wikipedia.org/wiki/Proscaline) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Proscaline?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.