Chemistry:3C-E

From HandWiki

3C-E, also known as 4-ethoxy-3,5-dimethoxyamphetamine or as α-methylescaline (3C-escaline), is a psychedelic drug of the phenethylamine, amphetamine, and 3C families related to 3,4,5-trimethoxyamphetamine (TMA).[1][2][3] It is the amphetamine (3C) analogue of escaline.[1][3]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 3C-E's dose as 30 to 60 mg orally and its duration as 8 to 12 hours.[1][4][2][3] Per other sources, it has an estimated typical dose of 45 mg orally.[5] The drug has about the same potency as escaline.[1][4][6]

The effects of 3C-E have been described as including strong visuals, closed-eye imagery like bright colors and distinct shapes, complex fantasy, strangeness, unworldliness, and unreality, an eerie state of awareness, fluctuating erotic and anti-erotic feelings, "exquisite sensitivity", heavy body discomfort, feelings of toxicity, nausea, muscle tremors, malaise, and slight teeth clenching.[1] Shulgin concluded that it was a fascinating compound, but that it was a little too heavy on the body for most subjects.[1]

Interactions

Pharmacology

Pharmacodynamics

3C-E is a potent serotonin 5-HT2A receptor agonist and also interacts with other serotonin receptors and targets.[3][2] It produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[7][5]

Chemistry

Synthesis

The chemical synthesis of 3C-E has been described.[1]

Analogues

Analogues of 3C-E include TMA, MEM, 3C-FE, 3C-DFE, and 3C-TFE, among others.[1][3][2]

History

3C-E was first described in the scientific literature by Benington and colleagues in 1954.[8] Alexander Shulgin and colleagues reported an active dose of 40 mg orally based on unpublished findings in a 1978 literature review.[9][10] Subsequently, Shulgin further reported the properties and effects of 3C-E in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.[1] The drug was encountered as a novel designer drug in Europe in 2013.[11][12][7]

Society and culture

Canada

It is a controlled substance in Canada under phenethylamine blanket-ban language.[13]

See also

  • 3C (psychedelics)

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 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.  PiHKAL entry
  2. ↑ 2.0 2.1 2.2 2.3 (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. pp. 736–737, 741. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "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. 
  4. ↑ 4.0 4.1 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://bibliography.maps.org/resources/download/12634. 
  5. ↑ 5.0 5.1 "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. [...]". 
  6. ↑ "Medicinal Chemistry and Structure–Activity Relationships". Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse. Academic Press. 1994. pp. 3–41. ISBN 978-0-12-173375-9. https://bitnest.netfirms.com/external/Books/AmphetamineAndItsAnalogs3. "α-Methylation also seems to have less of an effect on potency in 3,4,5-substituted compounds, with perhaps a 2-fold increase of activity from mescaline to its amphetamine counterpart. Fewer examples are available in this substitution series, but the α-methyl congener of escaline (3,5-dimethoxy-4-ethoxyphenethylarnine) is virtually equipotent to escaline (Shulgin and Shulgin, 1991)." 
  7. ↑ 7.0 7.1 "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. 
  8. ↑ "Synthesis of 4-Hydroxy- and 4-Ethoxy-3,5-dimethoxy-β-phenethylamines 1". Journal of the American Chemical Society 76 (21): 5555–5556. 1954. doi:10.1021/ja01650a084. ISSN 0002-7863. Bibcode: 1954JAChS..76.5555B. https://pubs.acs.org/doi/abs/10.1021/ja01650a084. Retrieved 18 October 2025. 
  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. ↑ "4-Ethoxy TMA / 4-Ethoxy-3,5-DMA / 3C-E". PIHKAL notebooks transcripts, Part II. p. 222. https://isomerdesign.com/pihkal/notebooks/transcripts/p2/p2.222.pdf. 
  11. ↑ "New drugs in Europe 2013". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA).. 2013. https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2013. 
  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. 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:3C-E&oldid=4309444"