2-Thioisomescaline

Pharmaceutical compound From Wikipedia, the free encyclopedia

2-Thioisomescaline (2-TIM), also known as 2-methylthio-3,4-dimethoxyphenethylamine, 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 2 position has been replaced with a methylthio group.[1][2][3][4] 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 names2-TIM; 2-Methylthio-3,4-dimethoxyphenethylamine; 3,4-Dimethoxy-2-methylthiophenethylamine
ATC code
  • None
Quick facts Clinical data, Other names ...
2-Thioisomescaline
Clinical data
Other names2-TIM; 2-Methylthio-3,4-dimethoxyphenethylamine; 3,4-Dimethoxy-2-methylthiophenethylamine
Routes of
administration
Oral[1]
Drug classPsychoactive drug
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1]
Identifiers
  • 2-(3,4-dimethoxy-2-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)SC)OC
  • InChI=1S/C11H17NO2S/c1-13-9-5-4-8(6-7-12)11(15-3)10(9)14-2/h4-5H,6-7,12H2,1-3H3
  • Key:NJNFCDQQEIAOIF-UHFFFAOYSA-N
Close

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2-TIM's dose as greater than 240 mg orally and its duration as unknown.[1][2][3] At a dose of 160 mg orally, there was some brief possible awareness.[1] In addition, a small amount of alcohol later that day was quite intoxicating.[1] On the other hand, there were no effects whatsoever at a higher dose of 240 mg orally.[1] Shulgin concluded that 2-TIM is inactive.[2]

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

2-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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