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4-MeS-DMT

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4-MeS-DMT
Clinical data
Other names4-SMe-DMT; 4-Methylthio-N,N-dimethyltryptamine
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • N,N-dimethyl-2-(4-methylsulfanyl-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H18N2S
Molar mass234.36 g·mol−1
3D model (JSmol)
  • CN(C)CCC1=CNC2=C1C(=CC=C2)SC
  • InChI=1S/C13H18N2S/c1-15(2)8-7-10-9-14-11-5-4-6-12(16-3)13(10)11/h4-6,9,14H,7-8H2,1-3H3
  • Key:YWCOPJQNWPEWQP-UHFFFAOYSA-N

4-MeS-DMT, or 4-SMe-DMT, also known as 4-methylthio-N,N-dimethyltryptamine, is a serotonin receptor modulator and possible psychedelic drug of the tryptamine family related to psilocin.[1][2][3][4] It is the 4-methylthio derivative of psilocin (4-HO-DMT) and is an analogue of 4-MeO-DMT.[1][2][3][4] The drug's properties and effects in humans are unknown.[1][4] It shows affinity for serotonin receptors.[2][3] 4-MeS-DMT produces psychedelic-like behavioral effects in animals, for instance generalization with 5-MeO-DMT in rodent drug discrimination tests, though is less potent than 5-MeS-DMT or 4-MeO-DMT.[1][2][4] The chemical synthesis of 4-MeS-DMT has been described.[1] 4-MeS-DMT was first described in the scientific literature by Richard Glennon and colleagues in 1982.[1][2][3][4] Subsequently, it was briefly described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) in 1997.[1]

See also

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References

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  1. ^ a b c d e f g Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "The 5-position on the indole ring of the tryptamine family is analogous to the 4-position in the phenethylamine family. And yet, here, with the 5-methoxy group of 5-MeO-DMT being replaced with the 5-methylthio group of 5-MeS-DMT, the activity actually seemed to decrease by a factor of two. Is this a generality of the tryptamines, or is this an anomaly of this one pair of compounds? There is the raw stuff potentially available to answer this question. There are a couple of compounds known with the sulfur in the 4-position, which is the location of the oxygen atom in psilocybin. The 4-thio analogues have been synthesized from 4-methylthio-indole, via the oxalyl chloride method and reaction with the appropriate amine. With dimethylamine, the indoleglyoxylamide was made in a 43% yield and had a mp 163–164 °C. With diisopropylamine, the amide was made in a 27% yield and had a mp 190–192 °C. The final amines were prepared by the reduction of these amides with LAH in THF. [N,N-Dimethyl-4-methylthiotryptamine] (4-MeS-DMT) was obtained in a 68% yield and melted at 108–110 °C; N,N-diisopropyl-4-methylthiotryptamine (4-MeS-DIPT) was obtained in a 61% yield and melted at 92–94 °C. In animal studies of behavioral disruption with these three compounds, there was systematic drop of potency in going from the 5-MeS-DMT to 4-MeS-DMT to 4-MeS-DIPT."
  2. ^ a b c d e 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.
  3. ^ a b c d 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.
  4. ^ a b c d e Glennon RA, Rosecrans JA (1982). "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neuroscience and Biobehavioral Reviews. 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].
[edit]
Tryptamines
No ring subs.
4-Hydroxytryptamines
5-Hydroxytryptamines
5-Methoxytryptamines
Other ring subs.
α-Alkyltryptamines
Others
Cyclized
Bioisosteres
Phenethylamines
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2C-x
3C-x
DOx
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Ψ-PEA
MDxx
FLY
25x-NB (NBOMes)
Others
Cyclized
Lysergamides
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Natural sources
5-HT1
5-HT1A
  • Positive allosteric modulators: Oleamide
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
  • Negative allosteric modulators: Oleamide
Tryptamines
4-Hydroxytryptamines
and esters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
α-Ketotryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
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