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| Other names | 5-Methylthio-2,4-dimethoxyamphetamine; 2,4-Dimethoxy-5-methylthioamphetamine; 5-Thio-TMA-2 |
| Routes of administration | Oral1 |
| Drug class | Psychoactive drug |
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| Pharmacokinetic data | |
| Duration of action | Unknown1 |
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| Formula | C12H19NO2S |
| Molar mass | 241.35 g·mol−1 |
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Meta-DOT, also known as 5-methylthio-2,4-dimethoxyamphetamine or as 5-thio-TMA-2, is a psychoactive drug of the phenethylamine and amphetamine families related to TMA-2.12 It is the analogue of TMA-2 in which the methoxy group at the 5 position has been replaced with a methylthio group.12 In addition, the drug is a positional isomer of Aleph (DOT; para-DOT).12
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists meta-DOT's dose as greater than 35 mg orally and its duration as unknown.12 The effects of meta-DOT have been reported to include threshold effects, a vague awareness of something or of a "thinness", and possibly some brief cardiovascular stimulation.1 However, the effects at tested doses were not said to be completely believable and Shulgin concluded that it was inactive.12 Higher doses were not tested.1
Meta-DOT has been found to produce hyperthermia in rabbits, albeit with approximately 30-fold lower potency than DOM, though with somewhat greater potency than mescaline.13
The chemical synthesis of meta-DOT has been described.13 Analogues of meta-DOT include TMA-2, Aleph (DOT; para-DOT; 4-thio-TMA-2), ortho-DOT (2-thio-TMA-2), 5-TOM (5-thio-DOM), and 5-TOET (5-thio-DOET), among others.12
Meta-DOT was first described in the scientific literature by Shulgin and colleagues in 1977.3 Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.1
References
References
- Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal125.shtml
- 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.
The two other possible oxygen substitutions of DOT have been synthesized and evaluated; this completes the three theoretical thio-analogues of TMA-2. 4,5-Dimethoxy-2-methylthioamphetamine and 2,4-dimethoxy-5-methylthioam-phetamine (Ortho-DOT and Meta-DOT respectively) were without any central effects at levels of 25mg orally.
- Jacob P, Anderson G, Meshul CK, Shulgin AT, Castagnoli N (October 1977). "Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane". J Med Chem. 20 (10): 1235–1239. doi:10.1021/jm00220a001. PMID 903913. Archived from the original on 2025-07-12.