2-TOM, also known as 2-methylthio-4-methyl-5-methoxyamphetamine or as 2-thio-DOM, is a psychedelic drug of the phenethylamine and amphetamine families related to the DOx psychedelic DOM. It is the analogue of DOM in which the methoxy group at the 2 position has been replaced with a methylthio group. The drug is one of two possible TOM (thio-DOM) positional isomers, the other being 5-TOM.
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2-TOM's dose as 60 to 100mg orally and its duration as 8 to 10hours. Whereas 2-TOM has a fully effective dose of around 80mg, DOM has a fully effective dose of about 5mg, and so there is around a 15-fold loss of potency with the drug. In addition, it has a shorter duration than DOM, with DOM having a listed duration of 14 to 20hours.
The effects of 2-TOM have been reported to include closed-eye visuals, feeling strange, "superb body feeling", pleasantness, bodily awareness, and feeling heavy. It has none of the neurological or physical "roughness" that was observed with 5-TOM.
The chemical synthesis of 2-TOM has been described. The phenethylamine analogue, 2C-2-TOM (2-thio-2C-D), has been synthesized, but was not tested and its properties are unknown. Bis-TOM, the 2,5-dimethylthio analogue of DOM, was synthesized and tested, but was inactive at doses of up to 160mg orally or approximately 50times the minimum effective dose of DOM.
2-TOM was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1983. Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.