4-MeS-DMT, or 4-SMe-DMT, also known as 4-methylthio-N,N-dimethyltryptamine, is a serotonin receptor modulator and possible psychedelic drug of the tryptamine family related to psilocin. "The 5-position on the indole ring of the tryptamine family is analogous to the 4-position in the phenethylamine family. And yet, here, with the 5-methoxy group of 5-MeO-DMT being replaced with the 5-methylthio group of 5-MeS-DMT, the activity actually seemed to decrease by a factor of two. Is this a generality of the tryptamines, or is this an anomaly of this one pair of compounds? There is the raw stuff potentially available to answer this question. There are a couple of compounds known with the sulfur in the 4-position, which is the location of the oxygen atom in psilocybin. The 4-thio analogues have been synthesized from 4-methylthio-indole, via the oxalyl chloride method and reaction with the appropriate amine. With dimethylamine, the indoleglyoxylamide was made in a 43% yield and had a mp 163–164 °C. With diisopropylamine, the amide was made in a 27% yield and had a mp 190–192 °C. The final amines were prepared by the reduction of these amides with LAH in THF. [N,N-Dimethyl-4-methylthiotryptamine] (4-MeS-DMT) was obtained in a 68% yield and melted at 108–110 °C; N,N-diisopropyl-4-methylthiotryptamine (4-MeS-DIPT) was obtained in a 61% yield and melted at 92–94 °C. In animal studies of behavioral disruption with these three compounds, there was systematic drop of potency in going from the 5-MeS-DMT to 4-MeS-DMT to 4-MeS-DIPT." It is the 4-methylthio derivative of psilocin (4-HO-DMT) and is an analogue of 4-MeO-DMT. The drug's properties and effects in humans are unknown. It shows affinity for serotonin receptors. 4-MeS-DMT produces psychedelic-like behavioral effects in animals, for instance generalization with 5-MeO-DMT in rodent drug discrimination tests, though is less potent than 5-MeS-DMT or 4-MeO-DMT. The chemical synthesis of 4-MeS-DMT has been described. 4-MeS-DMT was first described in the scientific literature by Richard Glennon and colleagues in 1982. Subsequently, it was briefly described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) in 1997.
See also Substituted tryptamine
References
External links 4-MeS-DMT - Isomer Design