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5-MeS-DMT

FieldValue
Verifiedfieldschanged
Watchedfieldschanged
verifiedrevid477225115
image5-MeS-DMT.svg
image_classskin-invert-image
width200px
image25-MeS-DMT 3D.png
image_class2bg-transparent
width2200px
routes_of_administrationSmoking
classSerotonergic psychedelic; Hallucinogen
ATC_prefixNone
onsetVery fast
duration_of_action10–30 minutes or
CAS_number_Ref
CAS_number5102-11-4
PubChem21180
ChemSpiderID_Ref
ChemSpiderID19917
UNII_Ref
UNII8E8PJ79K57
ChEMBL_Ref
ChEMBL31783
synonyms5-Methylthio-*N*,*N*-dimethyltryptamine; 5-Methylthio-DMT
IUPAC_name*N*,*N*-dimethyl-2-[5-(methylsulfanyl)-1*H*-indol-3-yl]ethan-1-amine
C13H=18N=2S=1
SMILESCN(CCC1=CNC2=C1C=C(SC)C=C2)C
StdInChI1S/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
StdInChIKey_Ref
StdInChIKeyYOGJZQGRTVMCPY-UHFFFAOYSA-N

| Drugs.com =

| elimination_half-life =

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

Use and effects

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

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.

Chemistry

Synthesis

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

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.

History

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

References

References

  1. "#46. 5-MES-DMT".
  2. (February 1982). "Hallucinogens as discriminative stimuli: a comparison of 4-OMe DMT and 5-OMe DMT with their methythio counterparts". Life Sciences.
  3. (August 1982). "Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety". Journal of Medicinal Chemistry.
  4. (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.
  5. "PhiKAL Notebook". isomer design.
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n,n-dialkyltryptamines methylthio-compounds psychedelic-tryptamines tihkal
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