S-DMT

S-DMT
Clinical data
Other names1-Thia-DMT; N,N-Dimethyl-3-(2-aminopropyl)benzo[β]thiophene; N,N-Dimethyl-3-AEBT
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 2-(1-benzothiophen-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H15NS
Molar mass205.32 g·mol−1
3D model (JSmol)
  • CN(C)CCC1=CSC2=CC=CC=C21
  • InChI=1S/C12H15NS/c1-13(2)8-7-10-9-14-12-6-4-3-5-11(10)12/h3-6,9H,7-8H2,1-2H3
  • Key:QAPUMUJBYRYLGE-UHFFFAOYSA-N

S-DMT, also known as 1-thia-DMT or as N,N-dimethyl-3-(2-aminoethyl)benzo[β]thiophene (N,N-dimethyl-3-AEBT), is a serotonin receptor modulator of the benzothiophene family related to the psychedelic tryptamine dimethyltryptamine (DMT).[1][2] It is the analogue and bioisostere of DMT in which the nitrogen atom of the indole ring has been replaced with a sulfur atom, making the drug a benzothiophene rather than indole or tryptamine derivative.[2] The drug shows about the same activity at the serotonin receptors in the rat fundus strip as DMT.[1][2][3][4] These receptors may correspond to the serotonin 5-HT2B receptor.[5][6] It has not been assessed at the serotonin 5-HT2A receptor.[1] S-DMT was first described in the scientific literature by Richard Glennon and colleagues by 1979.[1][2]

See also

References

  1. ^ a b c d Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X. Retrieved 9 January 2026. Early work with benzo[b]thiophenes 6 and 3-indenalkylamines 7 (Figure 5) demonstrated that for compounds lacking ring substituents, the ability to act as agonists in the rat fundus was about the same as for the tryptamines themselves.8 That is, the indole NH was not essential to activate the 5-HT2 receptor in the rat fundus. No modern studies have been carried out to assess affinity at 5-HT2A receptors.
  2. ^ a b c d Glennon RA, Gessner PK (April 1979). "Serotonin receptor binding affinities of tryptamine analogues". Journal of Medicinal Chemistry. 22 (4): 428–432. doi:10.1021/jm00190a014. PMID 430481.
  3. ^ Gupta SP, Singh P, Bindal MC (1 December 1983). "QSAR studies on hallucinogens". Chemical Reviews. 83 (6): 633–649. doi:10.1021/cr00058a003. ISSN 0009-2665. Retrieved 9 January 2026.
  4. ^ Gornez-Jeria JS, Morales-Lagos D, Cassels BK, Saavedra-Aguilar JC (1986). "Electronic Structure and Serotonin Receptor Binding Affinity of 7-Substituted Tryptamines QSAR of 7-Substituted Tryptamines". Quantitative Structure-Activity Relationships. 5 (4): 153–157. doi:10.1002/qsar.19860050404. ISSN 0931-8771. Retrieved 9 January 2026.
  5. ^ Baxter GS, Murphy OE, Blackburn TP (May 1994). "Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle". British Journal of Pharmacology. 112 (1): 323–331. doi:10.1111/j.1476-5381.1994.tb13072.x. PMC 1910288. PMID 8032658.
  6. ^ Nichols DE, Schooler D, Yeung MC, Oberlender RA, Zabik JE (September 1984). "Unreliability of the rat stomach fundus as a predictor of hallucinogenic activity in substituted phenethylamines". Life Sciences. 35 (13): 1343–1348. doi:10.1016/0024-3205(84)90390-4. PMID 6482656.
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