2-Thioisomescaline
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| Other names | 2-TIM; 2-Methylthio-3,4-dimethoxyphenethylamine; 3,4-Dimethoxy-2-methylthiophenethylamine |
| Routes of administration | Oral[1] |
| Drug class | Psychoactive drug |
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| Pharmacokinetic data | |
| Duration of action | Unknown[1] |
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| Chemical and physical data | |
| Formula | C11H17NO2S |
| Molar mass | 227.32 g·mol−1 |
| 3D model (JSmol) | |
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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]
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
- ^ a b c d e f g h i j k Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://www.erowid.org/library/books_online/pihkal/pihkal152.shtml
- ^ a b c d e Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on 13 July 2025.
- ^ a b c d Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.
- ^ a b c d e Jacob P, Shulgin AT (November 1981). "Sulfur analogues of psychotomimetic agents. Monothio analogues of mescaline and isomescaline". J Med Chem. 24 (11): 1348–1353. doi:10.1021/jm00143a017. PMID 7310812. Archived from the original on 2025-07-12.