Article · Wikipedia archive · Last revised Jul 21, 2026

Isamide

Isamide, also known as N-chloroacetyl-5-methoxytryptamine, is a serotonin receptor antagonist and the N-chloroacetyl derivative of 5-methoxytryptamine. It was first described in the scientific literature by 1969 and was first pharmacologically characterized by 1979.

Last revised
Jul 21, 2026
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Isamide
Clinical data
Other namesN-(1-Chloroacetyl)-5-methoxytryptamine
Drug classSerotonin receptor antagonist
Identifiers
  • 2-chloro-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H15ClN2O2
Molar mass266.73 g·mol−1
3D model (JSmol)
  • COC1=CC2=C(C=C1)NC=C2CCNC(=O)CCl
  • InChI=1S/C13H15ClN2O2/c1-18-10-2-3-12-11(6-10)9(8-16-12)4-5-15-13(17)7-14/h2-3,6,8,16H,4-5,7H2,1H3,(H,15,17)
  • Key:UCLPNTKRPMTACI-UHFFFAOYSA-N

Isamide, also known as N-chloroacetyl-5-methoxytryptamine, is a serotonin receptor antagonist and the N-chloroacetyl derivative of 5-methoxytryptamine.123 It was first described in the scientific literature by 1969 and was first pharmacologically characterized by 1979.42

See also

See also

References

References

  1. Frohlich PF, Meston CM (2000). "Evidence that serotonin affects female sexual functioning via peripheral mechanisms". Physiology & Behavior. 71 (3–4): 383–393. doi:10.1016/s0031-9384(00)00344-9. PMID 11150571.
  2. Huidobro-Toro JP, Huidobro F, Ruiz M (June 1979). "N-Chloroacetyl 5-methoxytryptamine (isamide): a selective antagonist of 5-hydroxytryptamine in the rat uterus". The Journal of Pharmacy and Pharmacology. 31 (6): 371–374. doi:10.1111/j.2042-7158.1979.tb13525.x. PMID 39134.
  3. Huidobro-Toro JP, Foree B (February 1980). "Dual agonist-antagonist effects of 5-hydroxytryptamine (5-HT) in the guinea pig ileum: evidence for a selective receptor desensitization effect". European Journal of Pharmacology. 61 (4): 335–345. doi:10.1016/0014-2999(80)90072-2. PMID 6102916.
  4. Kobayashi T, Spande TF, Aoyagi H, Witkop B (July 1969). "Tricyclic analogs of melatonin". Journal of Medicinal Chemistry. 12 (4): 636–638. doi:10.1021/jm00304a017. PMID 5793155.