5-MeS-DMT

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5-MeS-DMT
5-MeS-DMT.svg
Clinical data
Other names5-Methylthio-N,N-dimethyltryptamine; 5-Methylthio-DMT
Routes of
administration 		Smoking [1]
Drug class Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action Very fast [1]
Duration of action 10–30 minutes or <1 hour [1]
Identifiers
  • N,N-dimethyl-2-[5-(methylsulfanyl)-1H-indol-3-yl]ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C13H18N2S
Molar mass 234.36 g·mol−1
3D model (JSmol)
  • CN(CCC1=CNC2=C1C=C(SC)C=C2)C
  • InChI=1S/C13H18N2S/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3
  • Key:YOGJZQGRTVMCPY-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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]

Contents

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]

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 2 3 4 5 6 7 8 9 10 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252. "#46. 5-MES-DMT".
  2. 1 2 Glennon RA, Young R, Benington F, Morin RD (February 1982). "Hallucinogens as discriminative stimuli: a comparison of 4-OMe DMT and 5-OMe DMT with their methythio counterparts". Life Sciences. 30 (5): 465–467. doi:10.1016/0024-3205(82)90463-5. PMID   6801410.
  3. 1 2 Kline TB, Benington F, Morin RD, Beaton JM (August 1982). "Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety". Journal of Medicinal Chemistry. 25 (8): 908–913. doi:10.1021/jm00350a005. PMID   7120280.
  4. 1 2 Kline TB, Benington F, Morin RD, Beaton JM, Glennon RA, Domelsmith LN, et al. (November 1982). "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. doi:10.1021/jm00353a021. PMID   6815326.
  5. ↑ Shulgin A. "PhiKAL Notebook" (PDF). isomer design.
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