3C-E

3C-E
Clinical data
Other names4-Ethoxy-3,5-dimethoxyamphetamine; 3,5-Dimethoxy-4-ethoxyamphetamine; α-Methylescaline; 3C-Escaline
Routes of
administration		Oral[1][2][3][4]
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
  • CA: Schedule I
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
  • US: Analogue of a Schedule I drug, possibly illegal under the Federal Analog Act
Pharmacokinetic data
Duration of action8–12 hours[1][3]
Identifiers
  • 1-(4-Ethoxy-3,5-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H21NO3
Molar mass239.315 g·mol−1
3D model (JSmol)
  • CCOc1c(cc(cc1OC)CC(C)N)OC
  • InChI=1S/C13H21NO3/c1-5-17-13-11(15-3)7-10(6-9(2)14)8-12(13)16-4/h7-9H,5-6,14H2,1-4H3
  • Key:AHLXCGRWNKUNTQ-UHFFFAOYSA-N

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][5][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][2][5][3] Per other sources, it has an estimated typical dose of 45 mg orally.[4] The drug has about the same potency as escaline.[1][2][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

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

3C-E is a potent serotonin 5-HT2A receptor agonist and also interacts with other serotonin receptors and targets.[3][5] It produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[7][4]

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][5]

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

References

  1. ^ a b c d e f g h i j k Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. PiHKAL entry
  2. ^ a b c Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.
  3. ^ a b c d e f g 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. ^ a b c 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. [...]
  5. ^ a b c d 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, 741. ISBN 978-3-03788-700-4. OCLC 858805226.
  6. ^ Nichols DE (1994). "Medicinal Chemistry and Structure–Activity Relationships". In Cho AK, Segal DS (eds.). Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse. Academic Press. pp. 3–41. ISBN 978-0-12-173375-9. 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. ^ 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". Journal of Psychopharmacology. 33 (3): 406–414. doi:10.1177/0269881119826610. PMC 6848748. PMID 30789291.
  8. ^ Benington F, Morin RD, Clarke LC (1954). "Synthesis of 4-Hydroxy- and 4-Ethoxy-3,5-dimethoxy-β-phenethylamines 1". Journal of the American Chemical Society. 76 (21): 5555–5556. Bibcode:1954JAChS..76.5555B. doi:10.1021/ja01650a084. ISSN 0002-7863. Retrieved 18 October 2025.
  9. ^ 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.
  10. ^ Shulgin AT. "4-Ethoxy TMA / 4-Ethoxy-3,5-DMA / 3C-E" (PDF). PIHKAL notebooks transcripts, Part II. p. 222.
  11. ^ "New drugs in Europe 2013". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). 2013.
  12. ^ King LA (2014). "New phenethylamines in Europe". Drug Testing and Analysis. 6 (7–8): 808–818. doi:10.1002/dta.1570. PMID 24574327.
  13. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.