Chemistry:5-MeS-DMT

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5-MeS-DMT, also known as 5-methylthio-N,N-dimethyltryptamine or as 5-methylthio-DMT, is a lesser-known psychedelic drug of the tryptamine family.[1][2] It is the 5-methylthio derivative of dimethyltryptamine (DMT) and is an analogue of 5-MeO-DMT.[1][2]

Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin lists the dose as 15 to 30 mg smoked and its duration as less than 1 hour.[1] In individual reports, the duration was 10 to 30 minutes.[1] The effects included feeling stoned and no visuals, among others.[1] It was also described as coming on very fast and being quite intense.[1] The drug is said to be about half as potent as 5-MeO-DMT.[1]

Interactions

Pharmacology

Pharmacodynamics

5-MeS-DMT was less potent than 5-MeO-DMT and psilocin (4-HO-DMT) but more potent than 4-MeO-DMT or 4-MeS-DMT in rodent behavioral studies.[1][2][3][4][5] It is known produce generalization with 5-MeO-DMT in rodent drug discrimination tests, with only slightly lower potency in comparison.[2]

Chemistry

Synthesis

The chemical synthesis of 5-MeS-DMT has been described.[1]

Analogues

Analogues of 5-MeS-DMT include dimethyltryptamine (DMT), 5-MeO-DMT, 5,N,N-TMT (5-methyl-DMT; 5-Me-DMT), HBL20016 (5-MeS-6-F-DMT), and HBL20017 (4-F-5-MeS-DMT), among others.[1]

History

It was first described in the scientific literature by Richard Glennon and colleagues by 1982.[3][4][5] However, 5-MeS-DMT was synthesized and tested by Shulgin as early as 1979.[6]

See also

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 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.  "#46. 5-MES-DMT". https://www.erowid.org/library/books_online/tihkal/tihkal46.shtml. 
  2. ↑ 2.0 2.1 2.2 2.3 "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neurosci Biobehav Rev 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 "Benington, Morin and Kline (unpublished data) have recently prepared the 4-methylthio and 5-methylthio analogs of DMT, i.e., 4-SMe DMT (3k) and 5-SMe DMT (31), respectively.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].". 
  3. ↑ 3.0 3.1 "Hallucinogens as discriminative stimuli: a comparison of 4-OMe DMT and 5-OMe DMT with their methythio counterparts". Life Sciences 30 (5): 465–467. February 1982. doi:10.1016/0024-3205(82)90463-5. PMID 6801410. 
  4. ↑ 4.0 4.1 "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. 
  5. ↑ 5.0 5.1 "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. 
  6. ↑ "PhiKAL Notebook". isomer design. https://isomerdesign.com/pihkal/notebooks/transcripts/p3/p3.343.pdf. 



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