Chemistry:Meta-DOT
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
- ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 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/pihkal.shtml. http://www.erowid.org/library/books_online/pihkal/pihkal125.shtml
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://bibliography.maps.org/resources/download/12634. "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."
- ↑ 3.0 3.1 3.2 "Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane". J Med Chem 20 (10): 1235–1239. October 1977. doi:10.1021/jm00220a001. PMID 903913. https://bibliography.maps.org/resources/download/8601.
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