Chemistry:4-MeS-DMT

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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.[1][2][3][4] It is the 4-methylthio derivative of psilocin (4-HO-DMT) and is an analogue of 4-MeO-DMT.[1][2][3][4] The drug's properties and effects in humans are unknown.[1][4] It shows affinity for serotonin receptors.[2][3] 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.[1][2][4] The chemical synthesis of 4-MeS-DMT has been described.[1] 4-MeS-DMT was first described in the scientific literature by Richard Glennon and colleagues in 1982.[1][2][3][4] Subsequently, it was briefly described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) in 1997.[1]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml.  "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."
  2. ↑ 2.0 2.1 2.2 2.3 2.4 "Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety". Journal of Medicinal Chemistry 25 (8): 908–913. August 1982. doi:10.1021/jm00350a005. PMID 7120280. 
  3. ↑ 3.0 3.1 3.2 3.3 "Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives". Journal of Medicinal Chemistry 25 (11): 1381–1383. November 1982. doi:10.1021/jm00353a021. PMID 6815326. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neuroscience and Biobehavioral Reviews 6 (4): 489–497. 1982. doi:10.1016/0149-7634(82)90030-6. PMID 6757811. "Benington, Morin and Kline (unpublished data) have recently prepared the 4-methylthio and 5-methylthio analogs of DMT, i.e., 4-SMe DMT (3k) and 5-SMe DMT (31), respectively. In the discriminative stimulus assay, generalization occurs between 5-OMe DMT and both 4-SMe DMT and 5-SMe DMT, with the sulfur compounds being only slightly less active than their corresponding methoxy derivatives [29].". 



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