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5-MeS-DMT

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5-MeS-DMT
Clinical data
Other names5-Methylthio-N,N-dimethyltryptamine; 5-Methylthio-DMT
Routes of
administration		Smoking[1]
Drug classSerotonin receptor modulator; Serotonergic 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
PubChem CID
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 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

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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

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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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

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Synthesis

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

Analogues

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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

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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

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References

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  1. ^ a b c d e f g h i j k l m 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. ^ a b c d Glennon RA, Rosecrans JA (1982). "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neurosci Biobehav Rev. 6 (4): 489–497. 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. ^ a b 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.
  4. ^ a b 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.
  5. ^ a b 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.
  6. ^ Shulgin A. "PhiKAL Notebook" (PDF). isomer design.
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