Chemistry:5-MeS-DMT

From HandWiki

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] It is the 5-methylthio derivative of dimethyltryptamine (DMT) and is an analogue of 5-MeO-DMT.[1]

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 described as being 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.[2][3][4]

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, and 5,N,N-TMT (5-methyl-DMT; 5-Me-DMT), among others.[1]

History

It was first described in the scientific literature by Richard Glennon and colleagues by 1982.[2][3][4] However, 5-MeS-DMT was synthesized and tested by Shulgin as early as 1979.[5]

See also

References

  1. 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 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 "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. 
  3. 3.0 3.1 "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. 
  4. 4.0 4.1 "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. 
  5. "PhiKAL Notebook". isomer design. https://isomerdesign.com/pihkal/notebooks/transcripts/p3/p3.343.pdf.