3C-E

Psychedelic drug From Wikipedia, the free encyclopedia

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]

Other names4-Ethoxy-3,5-dimethoxyamphetamine; 3,5-Dimethoxy-4-ethoxyamphetamine; α-Methylescaline; 3C-Escaline
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
Quick facts Clinical data, Other names ...
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
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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

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

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