3-Thioescaline

Pharmaceutical compound From Wikipedia, the free encyclopedia

3-Thioescaline (3-TE), also known as 3-methoxy-4-ethoxy-5-methylthiophenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline.[1][2][3][4] It is the analogue of escaline in which the methoxy group at the 3 position has been replaced with a methylthio group.[1][2][3][4] The drug is one of two possible thioescaline (TE) positional isomers, the other being 4-thioescaline (4-TE).[1][2][3][4]

Other names3-TE; 3-Methoxy-4-ethoxy-5-methylthiophenethylamine; 4-Ethoxy-3-methoxy-5-methylthiophenethylamine; 4-Ethoxy-5-methoxy-3-methylthiophenethylamine
ATC code
  • None
Quick facts Clinical data, Other names ...
3-Thioescaline
Clinical data
Other names3-TE; 3-Methoxy-4-ethoxy-5-methylthiophenethylamine; 4-Ethoxy-3-methoxy-5-methylthiophenethylamine; 4-Ethoxy-5-methoxy-3-methylthiophenethylamine
Routes of
administration
Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action8–12 hours[1]
Identifiers
  • 2-(4-ethoxy-3-methoxy-5-methylsulfanylphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H19NO2S
Molar mass241.35 g·mol−1
3D model (JSmol)
  • CCOC1=C(C=C(C=C1SC)CCN)OC
  • InChI=1S/C12H19NO2S/c1-4-15-12-10(14-2)7-9(5-6-13)8-11(12)16-3/h7-8H,4-6,13H2,1-3H3
  • Key:LRYPRFGBZRIFIX-UHFFFAOYSA-N
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In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 3-thioescaline's dose as 60 to 80 mg orally and its duration as 8 to 12 hours.[1][2][3] The drug has approximately 5 or 6 times the potency of mescaline.[2][3][4][1] The effects of 3-thioescaline have been reported to include closed-eye imagery and fantasy, sounds having a deeper pitch, introspection, enhanced appreciation of art and music, time dilation, body load, and sleep disturbances.[1] It was said to be psychedelic rather than just intoxicating.[1] The desired psychoactive effects were said to outweigh its physical side effects.[1]

The chemical synthesis of 3-thioescaline has been described.[1][4]

3-Thioescaline was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1984.[4] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1]

See also

References

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