3C-E

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by Benington and colleagues in 1954.^[8] Alexander Shulgin and colleagues reported an active dose of 40 mg based on unpublished findings in a 1978 literature review.^[9][10] Subsequently, Shulgin further reported the properties and effects of 3C-E in his 1991 book PiHKAL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]

3C-E

Clinical data
Other names	4-Ethoxy-3,5-dimethoxyamphetamine; 3,5-Dimethoxy-4-ethoxyamphetamine; α-Methylescaline; 3C-Escaline
Routes of administration	Oral[1][2][3][4]
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[1][3]
Identifiers
IUPAC name 1-(4-Ethoxy-3,5-dimethoxyphenyl)propan-2-amine
CAS Number	146849-92-5 Y
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

See also

• 3C (psychedelics)
• 3C-P
• MEM