Isamide

Isamide
Clinical data
Other namesN-(1-Chloroacetyl)-5-methoxytryptamine
Drug classSerotonin receptor antagonist
Identifiers
IUPAC name
  • 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)
SMILES
  • COC1=CC2=C(C=C1)NC=C2CCNC(=O)CCl
InChI
  • 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.[1][2][3] It was first described in the scientific literature by 1969 and was first pharmacologically characterized by 1979.[4][2]

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. 1 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.


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