3C-P

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Wikipedia

3C-P
Clinical data
Other names4-Propoxy-3,5-dimethoxyamphetamine; 3,5-Dimethoxy-4-propoxyamphetamine; α-Methylproscaline; 3C-Proscaline
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
  • 1-(3,5-dimethoxy-4-propoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H23NO3
Molar mass253.342 g·mol−1
3D model (JSmol)
  • CC(N)Cc1cc(OC)c(OCCC)c(c1)OC
  • InChI=1S/C14H23NO3/c1-5-6-18-14-12(16-3)8-11(7-10(2)15)9-13(14)17-4/h8-10H,5-7,15H2,1-4H3 checkY
  • Key:KKMCHCCXGKYEKJ-UHFFFAOYSA-N checkY
  (verify)

3C-P, also known as 4-propoxy-3,5-dimethoxyamphetamine or as α-methylproscaline (3C-proscaline), is a psychedelic drug of the phenethylamine, amphetamine, and 3C families related to 3,4,5-trimethoxyamphetamine (TMA).[2][3] It is the amphetamine (3C) analogue of proscaline.[2][3] The drug has been reported to have a dose range of 20 to 40 mg orally, with a typical dose estimate of 30 mg, based on informal anecdotal reports.[1] Although 3C-P produces hallucinogenic effects, very little is known about its effects.[4] The chemical synthesis of 3C-P has been described.[5] 3C-P acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor.[3][6] It produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[4][1][6] 3C-P was first described in the scientific literature by Otakar Leminger by 1972.[7][8] Alexander Shulgin mentioned it in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved)[2] and Daniel Trachsel synthesized it in 2002 but neither reported its effects or properties.[5][9][10] The drug has been sold online as a designer drug and was first detected in September 2013 in Finland.[11][12]

See also

References

  1. 1 2 3 Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152. Table 4 Human potency data for selected hallucinogens. [...]
  2. 1 2 3 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  3. 1 2 3 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". Frontiers in Pharmacology. 12 794254. doi:10.3389/fphar.2021.794254. PMC 8865417. PMID 35222010.
  4. 1 2 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". Journal of Psychopharmacology. 33 (3): 406–414. doi:10.1177/0269881119826610. PMC 6848748. PMID 30789291.
  5. 1 2 Trachsel D (September 2002). "Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur-Aktivitätsbeziehungen, Mitteilung 1, Mescalin Derivate". Helvetica Chimica Acta. 85 (9): 3019–3026. doi:10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4.
  6. 1 2 Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nature Communications. 14 (1) 8221. Bibcode:2023NatCo..14.8221W. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.
  7. ↑ Leminger O (1972). "The Chemistry of Alkoxylated Phenethylamines – Part 2". Chemický Průmysl. 22: 553.
  8. ↑ Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978). "Mescaline Analogs: Substitutions at the 4-Position" (PDF). In Barnett G, Trsic M, Willette RE (eds.). QuaSAR: Quantitative Structure Activity Relationships Of Analgesics, Narcotic Antagonists, And Hallucinogens (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 22. National Institute on Drug Abuse. pp. 27–37. PMID 101882.
  9. ↑ 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. pp. 736–737. ISBN 978-3-03788-700-4. OCLC 858805226.
  10. ↑ Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
  11. ↑ "EMCDDA–Europol 2013 Annual Report on the implementation of Council Decision 2005/387/JHA | www.euda.europa.eu". www.euda.europa.eu. Retrieved 2025-05-11.
  12. ↑ King LA (2014). "New phenethylamines in Europe". Drug Testing and Analysis. 6 (7–8): 808–818. doi:10.1002/dta.1570. PMID 24574327.