Chemistry:Bis-TOM
Bis-TOM, or 2,5-TOM, also known as 4-methyl-2,5-dimethylthioamphetamine or as 2,5-dithio-DOM, is a chemical compound of the phenethylamine and amphetamine families related to DOM.[1][2] It is the analogue of DOM in which the methoxy groups at the 2 and 5 positions have been replaced with methylthio groups.[1][2]
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists bis-TOM's dose as greater than 160 mg orally and its duration as unknown.[1][2] The effects of bis-TOM have been reported to include vague awareness of something and "a suggestion of darting, physically (when going to sleep)", but no mental effects.[1] Shulgin concluded that bis-TOM was inactive, at least at tested doses of up to 160 mg orally.[1][2] Based on the approximate 15-fold loss of potency of 2-TOM compared to DOM and the approximate 10-fold drop in potency of 5-TOM relative to DOM, Shulgin hypothesized that bis-TOM might have a potency reduction of 150-fold and might be active at a dose of around 750 mg orally.[1] However, higher doses were not tested owing in parts to hints of neurological toxicity as the potential rewards were not considered worth the risks.[1]
The chemical synthesis of bis-TOM has been described.[1] The phenethylamine (2C) analogue of bis-TOM is 2C-bis-TOM.[1] This compound was synthesized by Shulgin but was not tested in humans.[1] According to Shulgin, 2C-bis-TOM would probably not be active.[1]
Bis-TOM was first described in the scientific literature by Shulgin and Peyton Jacob III in 1983.[3] Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.[1]
See also
References
- ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 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. https://www.erowid.org/library/books_online/pihkal/pihkal012.shtml
- ↑ 2.0 2.1 2.2 2.3 "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.
- ↑ "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. https://bibliography.maps.org/resources/download/8592.
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