5-MeS-DMT

5-MeS-DMT
Names
	Preferred IUPAC name N,N-Dimethyl-2-[5-(methylsulfanyl)-1H-indol-3-yl]ethan-1-amine
	Other names 5-Methylthio-N,N-dimethyltryptamine
Identifiers
CAS Number	5102-11-4 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL31783 ;
ChemSpider	19917 ;
PubChem CID	21180;
UNII	8E8PJ79K57 ;
CompTox Dashboard (EPA)	DTXSID50199019 ;
	InChI 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 ; InChI=1/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-UHFFFAOYAL;
	SMILES CN(CCC1=CNC2=C1C=C(SC)C=C2)C;
Properties
Chemical formula	C13H18N2S
Molar mass	234.36 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

5-MeS-DMT (5-methylthio-N,N-dimethyltryptamine) is a lesser-known psychedelic drug. It is the 5-methyl thio analog of dimethyltryptamine (DMT). 5-MeS-DMT was first synthesized by Alexander Shulgin. In his book TiHKAL (Tryptamines I Have Known and Loved), the minimum dosage is listed as 15-30 mg.^[1] The duration listed as very short (less than one hour), just like DMT. 5-MeS-DMT produces similar effects to DMT, but weaker. Shulgin describes his feelings while on a low dose of this drug as "pointlessly stoned", although at a higher dose of 20 mg he says it is "quite intense" and suggests that a higher dose still might have full activity.

5-MeS-DMT has been the subject of only limited clinical testing, with several small behavioral studies in rats indicating that it is a less potent than 5-MeO-DMT or 4-hydroxy-DMT (psilocin) but more effective than either 4-MeO-DMT or 4-MeS-DMT.^[2]^[3]^[4]

References

^ 5-MeS-DMT Entry in TIHKAL
^ Glennon, R.A.; Young, R.; Benington, F.; Morin, R.D. (February 1982). "Hallucinogens as discriminative stimuli: A comparison of 4-OMe and 5-OMe DMT with their methylthio counterparts". Life Sciences. 30 (5): 465–467. doi:10.1016/0024-3205(82)90463-5. PMID 6801410.
^ 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): 908–13. doi:10.1021/jm00350a005. PMID 7120280.
^ Kline TB; Benington F; Morin RD; Beaton JM; Glennon RA; Domelsmith LN; Houk KN; Rozeboom MD (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): 1381–3. doi:10.1021/jm00353a021. PMID 6815326.

[1] 5-MeS-DMT Entry in TIHKAL

[2] Glennon, R.A.; Young, R.; Benington, F.; Morin, R.D. (February 1982). "Hallucinogens as discriminative stimuli: A comparison of 4-OMe and 5-OMe DMT with their methylthio counterparts". Life Sciences. 30 (5): 465–467. doi:10.1016/0024-3205(82)90463-5. PMID 6801410.

[pmid7120280-3] 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): 908–13. doi:10.1021/jm00350a005. PMID 7120280.

[pmid6815326-4] Kline TB; Benington F; Morin RD; Beaton JM; Glennon RA; Domelsmith LN; Houk KN; Rozeboom MD (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): 1381–3. doi:10.1021/jm00353a021. PMID 6815326.

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5-MeS-DMT

See also

References