3C-E

3C-E
Clinical data
Other names	4-Ethoxy-3,5-dimethoxyamphetamine; 3,5-Dimethoxy-4-ethoxyamphetamine; α-Methylescaline; 3C-Escaline
Routes of; administration	Oral
Drug class	Serotonin 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 action	8–12 hours
Identifiers
	IUPAC name 1-(4-Ethoxy-3,5-dimethoxyphenyl)propan-2-amine;
CAS Number	146849-92-5 ;
PubChem CID	44350137;
ChemSpider	21106237;
UNII	W9QX56V5RU;
ChEMBL	ChEMBL128038;
CompTox Dashboard (EPA)	DTXSID40658382 ;
Chemical and physical data
Formula	C13H21NO3
Molar mass	239.315 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOc1c(cc(cc1OC)CC(C)N)OC;
	InChI 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] The drug has a dose range of 30 to 60 mg orally, with a typical dose estimate of 45 mg, and a duration of 8 to 12 hours.^[1]^[2]^[5]^[3]^[4] It has about the same potency as escaline.^[1]^[2]^[6] The drug is a potent serotonin 5-HT_2A 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] 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by Benington and colleagues in 1954.^[8] Alexander Shulgin and colleagues reported an active dose of 40 mg based on unpublished findings in a 1978 literature review.^[9]^[10] Subsequently, Shulgin further reported the properties and effects of 3C-E in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1] The drug was encountered as a novel designer drug in Europe in 2013.^[11]^[12]^[7]

References

^ ^a ^b ^c ^d ^e ^f ^g PiHKAL entry
^ ^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.
^ ^a ^b ^c ^d ^e ^f 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.
^ ^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. [...]
^ ^a ^b ^c 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.
^ 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).
^ ^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.
^ 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.
^ 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.
^ Shulgin AT. "4-Ethoxy TMA / 4-Ethoxy-3,5-DMA / 3C-E" (PDF). PIHKAL notebooks transcripts, Part II. p. 222.
^ "New drugs in Europe 2013". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). 2013.
^ King LA (2014). "New phenethylamines in Europe". Drug Testing and Analysis. 6 (7–8): 808–818. doi:10.1002/dta.1570. PMID 24574327.

External links

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[PiHKAL-1] ^ ^a ^b ^c ^d ^e ^f ^g PiHKAL entry

[Shulgin_2003-2] 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.

[Kolaczynska_2021-3] ^ ^a ^b ^c ^d ^e ^f 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.

[Halberstadt_2020-4] 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. [...]

[Trachsel_2013-5] 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. pp. 736–737, 741. ISBN 978-3-03788-700-4. OCLC 858805226.

[Nichols_1994-6] 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).

[Halberstadt_2019-7] 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.

[Benington_1954-8] 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.

[Braun_1978-9] 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.

[cited3676b86-10] Shulgin AT. "4-Ethoxy TMA / 4-Ethoxy-3,5-DMA / 3C-E" (PDF). PIHKAL notebooks transcripts, Part II. p. 222.

[EMCDDA2013-11] "New drugs in Europe 2013". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). 2013.

[King_2014-12] King LA (2014). "New phenethylamines in Europe". Drug Testing and Analysis. 6 (7–8): 808–818. doi:10.1002/dta.1570. PMID 24574327.

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External links