3C (psychedelics)

{{Short description|Class of chemical compounds}}

File:Trimethoxyamphetamine.svg (3,4,5-TMA; TMA-1).]]

3C (3C-x), also known as 4-substituted 3,5-dimethoxyamphetamines, substituted 3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1) analogues, or 3C-scalines, is a general name for the family of psychedelic amphetamines containing methoxy groups at the 3 and 5 positions of the benzene ring.{{cite book | last1=Shulgin | first1=A. | last2=Manning | first2=T. | last3=Daley | first3=P.F. | title=The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds | publisher=Transform Press | location=Berkeley | volume=1 | year=2011 | isbn=978-0-9630096-3-0 | url=https://books.google.com/books?id=68-huAAACAAJ | access-date=2 November 2024 }}{{CitePiHKAL}} These compounds are analogues of 3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1).

The 3C drugs are not the amphetamine counterparts of the 2C drugs, which are 4-substituted 2,5-dimethoxyphenethylamines. Instead, the DOx drugs, which are 4-substituted 2,5-dimethoxyamphetamines, are the amphetamine counterparts of the 2C drugs. The 3C drugs are the amphetamine counterparts of substituted mescaline analogues (4-substituted 3,5-dimethoxyphenethylamines). Moreover, in terms of naming with the "3C" prefix, the 3C drugs are generally actually derivatives of TMA-1 with the 4-position methoxy group extended rather than having any 4-position substituent. In this regard, they would be the 3,5-dimethoxyamphetamine counterparts of the 2C-O (2,4,5-trimethoxyphenethylamine) drugs (e.g., 2C-O-4) and the 2,4,5-trimethoxyamphetamine (2,4,5-TMA; TMA-2) derivatives (e.g., MEM).{{cite journal | vauthors = Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME | title = Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines | journal = Front Pharmacol | volume = 10 | issue = | pages = 1423 | date = 2019 | pmid = 31849671 | pmc = 6893898 | doi = 10.3389/fphar.2019.01423 | doi-access = free | url = }}

3C drugs have been developed and/or studied by Alexander Shulgin and Daniel Trachsel,{{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 }}{{cite journal | last=Trachsel | first=Daniel | title=Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur-Aktivitätsbeziehungen, Mitteilung 1, Mescalin Derivate | trans-title=Synthesis of new (phenylalkyl)amines for the investigation of structure-activity relationships, Communication 1, Mescaline derivatives | journal=Helvetica Chimica Acta | volume=85 | issue=9 | date=2002 | doi=10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4 | pages=3019–3026 | url=https://www.erowid.org/archive/rhodium/pdf/mescaline.4-subst.analogs.pdf }}{{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 = }}{{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 = | pages = 794254 | date = 2021 | pmid = 35222010 | pmc = 8865417 | doi = 10.3389/fphar.2021.794254 | doi-access = free | url = }} among others.{{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 = }}{{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 | pages = 8221 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 | url = }} The pharmacology of 3C drugs has been studied and described.