Meta-DOT
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| Clinical data | |
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| Other names | 5-Methylthio-2,4-dimethoxyamphetamine; 2,4-Dimethoxy-5-methylthioamphetamine; 5-Thio-TMA-2 |
| 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 | 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.[1][2] It is the analogue of TMA-2 in which the methoxy group at the 5 position has been replaced with a methylthio group.[1][2] In addition, the drug is a positional isomer of Aleph (DOT; para-DOT).[1][2]
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.[1][2] 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.[1][2] 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.[1][3]
The chemical synthesis of meta-DOT has been described.[1][3] 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.[1][2]
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]
See also
- Substituted methoxyphenethylamine
- DOx § Related compounds
- Meta-DOB (5-bromo-TMA-2)
References
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- ^ a b c d e f g h i j k l m Page Module:Citation/CS1/styles.css has no content.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
- ^ a b c d e f Page Module:Citation/CS1/styles.css has no content.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.
- ^ a b c Page Module:Citation/CS1/styles.css has no content.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.
External links
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