3C (psychedelics)

3,4,5-Trimethoxyamphetamine (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.[1][2] These compounds are analogues of 3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1).[1][2]

The 3C drugs are not the amphetamine counterparts of the 2C drugs, which are 4-substituted 2,5-dimethoxyphenethylamines.[1][2] Instead, the DOx drugs, which are 4-substituted 2,5-dimethoxyamphetamines, are the amphetamine counterparts of the 2C drugs.[1][2] The 3C drugs are the amphetamine counterparts of substituted mescaline analogues (4-substituted 3,5-dimethoxyphenethylamines).[1][2] 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.[1][2] 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).[3][4]

3C drugs have been developed and/or studied by Alexander Shulgin[1][2] and Daniel Trachsel,[5][6][4][7] among others.[8][9] The pharmacology of 3C drugs has been studied and described.[7][8]

List of 3C drugs

4-Methoxylated

  • 3,4,5-Trimethoxyamphetamine (3,4,5-TMA; TMA-1; 3C-mescaline)
  • 3C-AL (3C-allylescaline) (4-allyloxy-3,5-dimethoxyamphetamine)
  • 3C-BZ (3C-benzscaline) (4-benzyloxy-3,5-dimethoxyamphetamine)
  • 3C-CPM (3C-cyclopropylmescaline) (4-cyclopropylmethoxy-3,5-dimethoxyamphetamine)
  • 3C-DFE (3C-difluoroescaline) (4-(2,2-difluoroethoxy)-3,5-dimethoxyamphetamine)
  • 3C-DFM (3C-difluoromescaline) (4-(2,2-difluoromethoxy)-3,5-dimethoxyamphetamine)
  • 3C-E (3C-escaline) (4-ethoxy-3,5-dimethoxyamphetamine)
  • 3C-FE (3C-fluoroescaline) (4-(2-fluoroethoxy)-3,5-dimethoxyamphetamine)
  • 3C-FP (3C-fluoroproscaline) (4-(3-fluoropropoxy)-3,5-dimethoxyamphetamine)
  • 3C-IB (3C-isobuscaline) (4-isobutoxy-3,5-dimethoxyamphetamine)
  • 3C-IP (3C-isoproscaline) (4-isopropoxy-3,5-dimethoxyamphetamine)
  • 3C-MAL (3C-methallylescaline) (4-methallyloxy-3,5-dimethoxyamphetamine)
  • 3C-P (3C-proscaline) (4-propoxy-3,5-dimethoxyamphetamine)
  • 3C-TFE (3C-trifluoroescaline) (4-(2,2,2-trifluoroethoxy)-3,5-dimethoxyamphetamine)

Other 4-substituted

  • 4-Br-3,5-DMA (4-bromo-3,5-dimethoxyamphetamine)
  • 4-I-3,5-DMA (4-iodo-3,5-dimethoxyamphetamine)
  • 4-PhPr-3,5-DMA (4-(3-phenylpropyl)-3,5-dimethoxyamphetamine)
  • Methyl-TMA (N-methyl-TMA) (N-methyl-3,4,5-trimethoxyamphetamine)

See also

References

  1. ^ a b c d e f g 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 g Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  3. ^ Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2019). "Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines". Front Pharmacol. 10: 1423. doi:10.3389/fphar.2019.01423. PMC 6893898. PMID 31849671.
  4. ^ a b Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Test Anal. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
  5. ^ 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.
  6. ^ Trachsel, Daniel (2002). "Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur-Aktivitätsbeziehungen, Mitteilung 1, Mescalin Derivate" [Synthesis of new (phenylalkyl)amines for the investigation of structure-activity relationships, Communication 1, Mescaline derivatives] (PDF). Helvetica Chimica Acta. 85 (9): 3019–3026. doi:10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4.
  7. ^ a b Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2021). "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines". Front Pharmacol. 12: 794254. doi:10.3389/fphar.2021.794254. PMC 8865417. PMID 35222010.
  8. ^ a b Halberstadt AL, Chatha M, Chapman SJ, Brandt SD (March 2019). "Comparison of the behavioral effects of mescaline analogs using the head twitch response in mice". J Psychopharmacol. 33 (3): 406–414. doi:10.1177/0269881119826610. PMC 6848748. PMID 30789291.
  9. ^ 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 (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun. 14 (1): 8221. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.


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