5-TOM
5-TOM, also known as 2-methoxy-4-methyl-5-methylthioamphetamine or as 5-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 5 position has been replaced with a methylthio group. The drug is one of two possible TOM positional isomers, the other being 2-TOM.
In his book PiHKAL and other publications, Alexander Shulgin lists 5-TOM's dose as 30 to 50mg orally and its duration as 6 to 10hours. Its onset is about 30minutes and its time to peak is a little over 3hours. Whereas 5-TOM has an effective dose of around 40mg, DOM has a fully effective dose of about 5mg, and so there is around an 8-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 5-TOM have been reported to include sensory enhancement, closed-eye imagery and fantasy, substantial open-eye visuals and some visual distortions, catatonia-like state, "pretty heavy-duty experience", body load, generalized discomfort or malaise, neurological discoordination, gastrointestinal disturbance such as cramping and nausea, irritability, anger, sleep disturbance, and next-day lethargy. According to Shulgin, there were no completely positive experiences, more negative reports than positive ones, not even many neutral reports, and the consensus being that the drug wasn't worth the struggle. There also appears to be significant interindividual variability in intensity of 5-TOM.
The chemical synthesis of 5-TOM has been described. The phenethylamine analogue, 2C-5-TOM, 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. TOMSO is the sulfoxide of 5-TOM, and produced few effects on its own at doses of up to 150mg orally.
5-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.