Structure via PubChem · Public domain (PubChem)
Bis-TOM
Sign in to saveAlso known as 4-methyl-2,5-dimethylthio-alpha-methylphenethylamine, 2,5-bismethylthio-4-methylamphetamine, 4-methyl-2,5-bis-(methylthio)amphetamine, 1-[4-methyl-2,5-bis(methylsulfanyl)phenyl]propan-2-amine
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. It is the analogue of DOM in which the methoxy groups at the 2 and 5 positions have been replaced with methylthio groups.
Chemical data
- Formula
- C12H19NS2
- Molecular weight
- 241.4 g/mol
- IUPAC name
- 1-[4-methyl-2,5-bis(methylsulfanyl)phenyl]propan-2-amine
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 241.095891608
Show 2 more facts
- canonical SMILES
- CSc1cc(C)c(cc1CC(C)N)SC
- chemical formula
- C₁₂H₁₉NS₂
Sources (2)
via Wikidata · CC0
~2 min read
Article
3 sectionsContents
- See also
- References
- External links
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. It is the analogue of DOM in which the methoxy groups at the 2 and 5 positions have been replaced with methylthio groups.
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists bis-TOM's dose as greater than 160mg orally and its duration as unknown. 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. Shulgin concluded that bis-TOM was inactive, at least at tested doses of up to 160mg orally. 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 750mg orally. However, higher doses were not tested owing in parts to hints of neurological toxicity as the potential rewards were not considered worth the risks.