Jump to content

4C (psychedelics)

Add links
From Wikipedia, the free encyclopedia
Ariadne (4C-D).

4C (4C-x), also known as 4-substituted 2,5-dimethoxy-α-ethylphenethylamines, is a general name for the family of psychedelic and related phenylisobutylamines (α-ethylphenethylamines) having methoxy groups at the 2 and 5 positions of the phenyl ring and a 4-position substituent.[1][2][3][4] These compounds are analogues of the 2Cs and DOx drugs, but the α-alkyl chain has been further lengthed (0 carbons for 2C, 1 carbon for DOx, and 2 carbons for 4C).[1][2][3]

The most notable and well-known of the 4C drugs is Ariadne (4C-D).[1][2][3] This drug produces only threshold psychedelic effects and has been described as non-hallucinogenic or as having "the alert of a psychedelic, with none of the rest of the package".[2] These unique properties have made Ariadne of interest for potential therapeutic applications.[2] In contrast to Ariadne, other 4C drugs, such as 4C-B, have been reported to be more significantly psychedelic.[3] The pharmacology of the 4C drugs has been studied and they are known to act as serotonin 5-HT2A receptor agonists, but with lower efficacy than other related psychedelics like the 2Cs and DOx drugs.[4]

4C drugs have been developed and/or studied by Alexander Shulgin,[1][2] Daniel Trachsel,[3] and Michael Cunningham and colleagues.[4]

List of 4C drugs

[edit]
Structure Name(s) Chemical name CAS #
Ariadne (4C-D) 1-(2,5-Dimethoxy-4-methylphenyl)butan-2-amine 52842-59-8
4C-B 1-(2,5-Dimethoxy-4-bromophenyl)butan-2-amine 69294-23-1
4C-C 1-(2,5-Dimethoxy-4-chlorophenyl)butan-2-amine 791010-74-7
4C-E[5] 1-(2,5-Dimethoxy-4-ethylphenyl)butan-2-amine ?
4C-I 1-(2,5-Dimethoxy-4-iodophenyl)butan-2-amine 758631-75-3
4C-N 1-(2,5-Dimethoxy-4-nitrophenyl)butan-2-amine 775234-58-7
4C-P 1-(2,5-Dimethoxy-4-(n-propyl)phenyl)butan-2-amine ?
4C-T-2 1-[2,5-Dimethoxy-4-(ethylthio)phenyl]butan-2-amine 850007-13-5

See also

[edit]

References

[edit]
  1. ^ a b c d Shulgin, A.; Manning, T.; Daley, P.F. (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0. Retrieved 2 November 2024.
  2. ^ a b c d e f Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  3. ^ a b c d e Trachsel, D.; Lehmann, D.; Enzensperger, C. (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Retrieved 31 January 2025.
  4. ^ a b c Cunningham MJ, Bock HA, Serrano IC, Bechand B, Vidyadhara DJ, Bonniwell EM, Lankri D, Duggan P, Nazarova AL, Cao AB, Calkins MM, Khirsariya P, Hwu C, Katritch V, Chandra SS, McCorvy JD, Sames D (January 2023). "Pharmacological Mechanism of the Non-hallucinogenic 5-HT2A Agonist Ariadne and Analogs". ACS Chemical Neuroscience. 14 (1): 119–135. doi:10.1021/acschemneuro.2c00597. PMC 10147382. PMID 36521179.
  5. ^ Shulgin AT. Treatment of senile geriatric patients to restore performance. Patent US 4034113
[edit]


Retrieved from "https://en.wikipedia.org/w/index.php?title=4C_(psychedelics)&oldid=1292439849"