Chemistry:S-DMT

From HandWiki

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. ↑ 1.0 1.1 1.2 1.3 "Structure–activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling 1 (5): 559–579. 2012. doi:10.1002/wmts.42. ISSN 2190-460X. https://onlinelibrary.wiley.com/doi/10.1002/wmts.42. 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. ↑ 2.0 2.1 2.2 2.3 "Serotonin receptor binding affinities of tryptamine analogues". Journal of Medicinal Chemistry 22 (4): 428–432. April 1979. doi:10.1021/jm00190a014. PMID 430481. 
  3. ↑ "QSAR studies on hallucinogens". Chemical Reviews 83 (6): 633–649. 1 December 1983. doi:10.1021/cr00058a003. ISSN 0009-2665. https://pubs.acs.org/doi/abs/10.1021/cr00058a003. Retrieved 9 January 2026. 
  4. ↑ "Electronic Structure and Serotonin Receptor Binding Affinity of 7-Substituted Tryptamines QSAR of 7-Substituted Tryptamines". Quantitative Structure-Activity Relationships 5 (4): 153–157. 1986. doi:10.1002/qsar.19860050404. ISSN 0931-8771. https://onlinelibrary.wiley.com/doi/10.1002/qsar.19860050404. Retrieved 9 January 2026. 
  5. ↑ "Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle". British Journal of Pharmacology 112 (1): 323–331. May 1994. doi:10.1111/j.1476-5381.1994.tb13072.x. PMID 8032658. 
  6. ↑ "Unreliability of the rat stomach fundus as a predictor of hallucinogenic activity in substituted phenethylamines". Life Sciences 35 (13): 1343–1348. September 1984. doi:10.1016/0024-3205(84)90390-4. PMID 6482656. 



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