4-Thiometaescaline
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| Other names | 4-TME; 3-Ethoxy-4-methylthio-5-methoxyphenethylamine; 3-Ethoxy-5-methoxy-4-methylthiophenethylamine |
| Routes of administration | Oral[1] |
| Drug class | Psychoactive drug |
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| Duration of action | 10–15 hours[1] |
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| Chemical and physical data | |
| Formula | C12H19NO2S |
| Molar mass | 241.35 g·mol−1 |
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4-Thiometaescaline (4-TME), also known as 3-ethoxy-4-methylthio-5-methoxyphenethylamine, is a psychoactive drug of the phenethylamine and scaline families related to mescaline.[1][2][3] It is the analogue of metaescaline in which the methoxy group at the 4 position has been replaced with a methylthio group.[1][2][3] The drug is one of three possible positional isomers of thiometaescaline (TME), the others being 3-thiometaescaline (3-TME) and 5-thiometaescaline (5-TME).[1][2][3]
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 4-TME's dose as 60 to 100 mg orally and its duration as 10 to 15 hours.[1][2] The drug has approximately 4 times the potency of mescaline, though its effects are very different.[2][1][3] The effects of 4-TME have been reported to include mild mental changes that were neither visual nor particularly interesting, a strange off-baseness, feeling sad and morbid, mild gastrointestinal disturbances, sleep disturbances, and subsequent-day negative effects like lethargy and emotional disconnection.[1] It was described as being more toxic than joyous.[1] No clear hallucinogenic or perceptual effects were described.[1]
The chemical synthesis of 4-TME has been described.[1][3] It is said to have a very small yield.[1]
4-TME was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1984.[3] 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 l m 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/pihkal164.shtml
- ^ a b c d e 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 f Jacob P, Shulgin AT (July 1984). "Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothio analogues". J Med Chem. 27 (7): 881–888. doi:10.1021/jm00373a013. PMID 6737431.