Chemistry:3C-P

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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).[1][2] It is the amphetamine (3C) analogue of proscaline.[1][2]

Use and effects

3C-P 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.[3] Although 3C-P produces hallucinogenic effects, very little is known about its effects.[4]

Interactions

Pharmacology

Pharmacodynamics

3C-P acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor.[2][5] It produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[4][3][5]

Chemistry

Synthesis

The chemical synthesis of 3C-P has been described.[6]

Analogues

Analogues of 3C-P include TMA, MEM, 3C-E, 3C-AL, 3C-MAL, and 3C-FP, among others.[1][7][2]

History

3C-P was first described in the scientific literature by Otakar Leminger by 1972.[8][9] Alexander Shulgin mentioned it in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved)[1] and Daniel Trachsel synthesized it in 2002, but neither of them reported its properties or effects in humans.[6][7][10] The drug has been sold online as a designer drug and was first detected in September 2013 in Finland.[11][12]

Society and culture

Canada

3C-P is a controlled substance in Canada under amphetamine blanket-ban language.[13]

United States

3C-P is not an explicitly controlled substance in the United States, although it would most likely be considered a controlled substance under the Federal Analogue Act as an analogue of 2C-P.[14]

See also

  • 3C (psychedelics)

References

  1. ↑ 1.0 1.1 1.2 1.3 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml. 
  2. ↑ 2.0 2.1 2.2 2.3 "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines". Frontiers in Pharmacology 12. 2021. doi:10.3389/fphar.2021.794254. PMID 35222010. 
  3. ↑ 3.0 3.1 "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology 167. May 2020. doi:10.1016/j.neuropharm.2019.107933. PMID 31917152. PMC 9191653. http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf. "Table 4 Human potency data for selected hallucinogens. [...]". 
  4. ↑ 4.0 4.1 "Comparison of the behavioral effects of mescaline analogs using the head twitch response in mice". Journal of Psychopharmacology 33 (3): 406–414. March 2019. doi:10.1177/0269881119826610. PMID 30789291. 
  5. ↑ 5.0 5.1 "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nature Communications 14 (1). December 2023. doi:10.1038/s41467-023-44016-1. PMID 38102107. Bibcode: 2023NatCo..14.8221W. 
  6. ↑ 6.0 6.1 "Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur-Aktivitätsbeziehungen, Mitteilung 1, Mescalin Derivate". Helvetica Chimica Acta 85 (9): 3019–3026. September 2002. doi:10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4. 
  7. ↑ 7.0 7.1 (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. pp. 736–737. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  8. ↑ Otakar Leminger (1972). "Příspěvek k chemii v jádře alkoxylovaných β-fenoetylaminů – II: O některých v jádře alkoxylovaných β-fenoetylaminech, resp. jejich sulfátech". Chemický Průmysl 22: 553–557. https://isomerdesign.com/bitnest/external/ChemickyPrumysl/22.553. 
  9. ↑ "Mescaline Analogs: Substitutions at the 4-Position". QuaSAR: Quantitative Structure Activity Relationships Of Analgesics, Narcotic Antagonists, And Hallucinogens. National Institute on Drug Abuse Research Monograph Series. 22. National Institute on Drug Abuse. 1978. pp. 27–37. https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38. 
  10. ↑ "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis 4 (7–8): 577–590. 2012. 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". https://www.euda.europa.eu/publications/implementation-reports/2013_en. 
  12. ↑ "New phenethylamines in Europe". Drug Testing and Analysis 6 (7–8): 808–818. 2014. doi:10.1002/dta.1570. PMID 24574327. 
  13. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  14. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 

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