isamide

{{Short description|Serotonin antagonist}}

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| class = Serotonin receptor antagonist

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| CAS_number = 21424-91-9

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| PubChem = 192991

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| ChemSpiderID = 167480

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| synonyms = N-(1-Chloroacetyl)-5-methoxytryptamine

| IUPAC_name = 2-chloro-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide

| C=13 | H=15 | Cl=1 | N=2 | O=2

| SMILES = COC1=CC2=C(C=C1)NC=C2CCNC(=O)CCl

| StdInChI = 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)

| StdInChIKey = UCLPNTKRPMTACI-UHFFFAOYSA-N

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Isamide, also known as N-chloroacetyl-5-methoxytryptamine, is a serotonin receptor antagonist and the N-chloroacetyl derivative of 5-methoxytryptamine.{{cite journal | vauthors = Frohlich PF, Meston CM | title = Evidence that serotonin affects female sexual functioning via peripheral mechanisms | journal = Physiology & Behavior | volume = 71 | issue = 3–4 | pages = 383–393 | date = 2000 | pmid = 11150571 | doi = 10.1016/s0031-9384(00)00344-9 }}{{cite journal | vauthors = Huidobro-Toro JP, Huidobro F, Ruiz M | title = N-Chloroacetyl 5-methoxytryptamine (isamide): a selective antagonist of 5-hydroxytryptamine in the rat uterus | journal = The Journal of Pharmacy and Pharmacology | volume = 31 | issue = 6 | pages = 371–374 | date = June 1979 | pmid = 39134 | doi = 10.1111/j.2042-7158.1979.tb13525.x }}{{cite journal | vauthors = Huidobro-Toro JP, Foree B | title = Dual agonist-antagonist effects of 5-hydroxytryptamine (5-HT) in the guinea pig ileum: evidence for a selective receptor desensitization effect | journal = European Journal of Pharmacology | volume = 61 | issue = 4 | pages = 335–345 | date = February 1980 | pmid = 6102916 | doi = 10.1016/0014-2999(80)90072-2 }} It was first described in the scientific literature by 1969 and was first pharmacologically characterized by 1979.{{cite journal | vauthors = Kobayashi T, Spande TF, Aoyagi H, Witkop B | title = Tricyclic analogs of melatonin | journal = Journal of Medicinal Chemistry | volume = 12 | issue = 4 | pages = 636–638 | date = July 1969 | pmid = 5793155 | doi = 10.1021/jm00304a017 }}