4-Thiomescaline

Pharmaceutical compound From Wikipedia, the free encyclopedia

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

Other names4-TM; Thiomescaline; 3,5-Dimethoxy-4-methylthiophenethylamine; 4-Methylthio-3,5-dimethoxyphenethylamine; 3-MeO-4-MeS-5-MeO-PEA
ATC code
  • None
Quick facts Clinical data, Other names ...
4-Thiomescaline
Clinical data
Other names4-TM; Thiomescaline; 3,5-Dimethoxy-4-methylthiophenethylamine; 4-Methylthio-3,5-dimethoxyphenethylamine; 3-MeO-4-MeS-5-MeO-PEA
Routes of
administration
Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action30–60 minutes[1][2]
Duration of action10–15 hours[1]
Identifiers
  • 2-(3,5-dimethoxy-4-methylsulfanylphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17NO2S
Molar mass227.32 g·mol−1
3D model (JSmol)
  • COC1=CC(=CC(=C1SC)OC)CCN
  • InChI=1S/C11H17NO2S/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3
  • Key:FYTOAZIRBXNPKZ-UHFFFAOYSA-N
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In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 4-TM's dose as 20 to 40 mg orally and its duration as 10 to 15 hours.[1][3][4][2][5] Its onset is 30 to 60 minutes.[1][2] The drug has about 10 times the potency of mescaline.[1][3][4][5][6][7][8] The effects of 4-TM have been reported to include slight color enhancement, closed-eye imagery, fantasy, feeling strange, feelings of unreality, visions of Möbius strips, introspection, insights, lightheadedness, physical uneasiness, tremor, abdominal cramps, walking difficulty, appetite loss, and parasthesia.[1][2][5] Shulgin described it as a "mixed bag of responses".[1] It was described as being more similar in its effects to LSD than to mescaline and as being similar in effects to the Aleph series.[1][2]

The chemical synthesis of 4-TM has been described.[1][5][2]

4-TM was first synthesized and tested in 1977 and was described in the literature by Shulgin and colleagues in 1978.[4][2][5] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1]

See also

References

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