Chemistry:TOMSO
TOMSO, or 5-TOMSO, also known as 2-methoxy-4-methyl-5-methylsulfinylamphetamine, is a psychedelic drug of the phenethylamine and amphetamine families related to the DOx series.[1][2] It is the analogue of DOM in which the methoxy group at the 5 position has been replaced with a sulfur-containing methylsulfinyl group.[1][2]
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists TOMSO's dose as >150 mg orally alone or 100 to 150 mg orally in combination with alcohol and its duration as 10 to 16 hours.[1] TOMSO was reported to produce no or only threshold effects by itself at the assessed doses, but when alcohol was concomitantly ingested, clear hallucinogenic effects occurred.[1] These effects included facial distortion and remarkable time dilation, among others.[1] When combined with alcohol, "plus-two" and "plus-three" experiences occurred on the Shulgin Rating Scale.[1]
The chemical synthesis of TOMSO has been described.[1]
TOMSO was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1983.[2] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1]
See also
- Substituted methoxyphenethylamine
- 2-TOM, 5-TOM, and Bis-TOM
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 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. TOMSO entry
- ↑ 2.0 2.1 2.2 "Sulfur analogues of psychotomimetic agents. 2. Analogues of (2,5-dimethoxy-4-methylphenyl)-and (2,5-dimethoxy-4-ethylphenyl)isopropylamine". J Med Chem 26 (5): 746–752. May 1983. doi:10.1021/jm00359a021. PMID 6842515.
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