3-Thioisomescaline

Pharmaceutical compound From Wikipedia, the free encyclopedia

3-Thioisomescaline (3-TIM), also known as 2,4-dimethoxy-3-methylthiophenethylamine, is a chemical compound of the phenethylamine and scaline families related to mescaline.[1][2][3][4] It is the analogue of isomescaline in which the methoxy group at the 3 position has been replaced with a methylthio group.[1][2][3] The compound is one of two possible thioisomescaline (TIM) positional isomers, the others being 3-thioisomescaline (3-TIM) and 4-thioisomescaline (4-TIM).[1][2][3][4]

Other names3-TIM; 2,4-Dimethoxy-3-methylthiophenethylamine; 3-Methylthio-2,4-dimethoxyphenethylamine
ATC code
  • None
Quick facts Clinical data, Other names ...
3-Thioisomescaline
Clinical data
Other names3-TIM; 2,4-Dimethoxy-3-methylthiophenethylamine; 3-Methylthio-2,4-dimethoxyphenethylamine
Routes of
administration
Oral[1]
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1]
Identifiers
  • 2-(2,4-dimethoxy-3-methylsulfanylphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC11H17NO2S
Molar mass227.32 g·mol−1
3D model (JSmol)
  • COC1=C(C(=C(C=C1)CCN)OC)SC
  • InChI=1S/C11H17NO2S/c1-13-9-5-4-8(6-7-12)10(14-2)11(9)15-3/h4-5H,6-7,12H2,1-3H3
  • Key:LEELWLKZRKDMAS-UHFFFAOYSA-N
Close

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 3-TIM's dose as greater than 240 mg orally and its duration as unknown.[1][2][3] The effects of 3-TIM have been reported to include possible brief alert and mild stomach upset, with no other effects observed.[1] However, it is unclear that the preceding effects were actually caused by 3-TIM.[1] Shulgin concluded that 3-TIM is inactive.[2]

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

3-TIM was first described in the scientific literature by Shulgin and Peyton Jacob III in 1981.[4] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1]

See also

References

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