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5-MeS-DMT

From Wikipedia, the free encyclopedia

Pharmaceutical compound
5-MeS-DMT
Clinical data
Other names5-Methylthio-N,N-dimethyltryptamine; 5-Methylthio-DMT
Routes of
administration
Smoking[1]
Drug classSerotonergic psychedelic;Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of actionVery fast[1]
Duration of action10–30 minutes or <1 hour[1]
Identifiers
  • N,N-dimethyl-2-[5-(methylsulfanyl)-1H-indol-3-yl]ethan-1-amine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC13H18N2S
Molar mass234.36 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 checkY
 ☒NcheckY (what is this?)  (verify)

5-MeS-DMT, also known as5-methylthio-N,N-dimethyltryptamine or as5-methylthio-DMT, is a lesser-knownpsychedelic drug of thetryptamine family.[1] It is the 5-methylthioderivative ofdimethyltryptamine (DMT) and is ananalogue of5-MeO-DMT.[1]

Use and effects

[edit]

In his bookTiHKAL (Tryptamines I Have Known and Loved),Alexander Shulgin lists the dose as 15 to 30 mgsmoked and itsduration as less than 1 hour.[1] In individual reports, the duration was 10 to 30 minutes.[1] The effects included feelingstoned and novisuals, 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 aspotent as 5-MeO-DMT.[1]

Interactions

[edit]
See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Pharmacology

[edit]

Pharmacodynamics

[edit]

5-MeS-DMT was less potent than 5-MeO-DMT andpsilocin (4-HO-DMT) but more potent than4-MeO-DMT or4-MeS-DMT in rodent behavioral studies.[2][3][4]

Chemistry

[edit]

Synthesis

[edit]

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

Analogues

[edit]

Analogues of 5-MeS-DMT includedimethyltryptamine (DMT),5-MeO-DMT, and5,N,N-TMT (5-methyl-DMT; 5-Me-DMT), among others.[1]

History

[edit]

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

See also

[edit]

References

[edit]
  1. ^abcdefghijklShulgin A,Shulgin A (September 1997).TiHKAL: The Continuation.Berkeley, California:Transform Press.ISBN 0-9630096-9-9.OCLC 38503252."#46. 5-MES-DMT".
  2. ^abGlennon 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. ^abKline 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. ^abKline 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.

External links

[edit]
Tryptamines
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5-Hydroxytryptamines
5-Methoxytryptamines
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Tryptamines
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Isotryptamines
Related compounds
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