Isamide Explained

Class:	Serotonin receptor antagonist
Cas Number:	21424-91-9
Pubchem:	192991
Chemspiderid:	167480
Synonyms:	N-(1-Chloroacetyl)-5-methoxytryptamine
Iupac Name:	2-chloro-N-[2-(5-methoxy-1''H''-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

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]

Notes and References

1. Frohlich PF, Meston CM . Evidence that serotonin affects female sexual functioning via peripheral mechanisms . Physiology & Behavior . 71 . 3–4 . 383–393 . 2000 . 11150571 . 10.1016/s0031-9384(00)00344-9 .
2. Huidobro-Toro JP, Huidobro F, Ruiz M . 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 . June 1979 . 39134 . 10.1111/j.2042-7158.1979.tb13525.x .
3. Huidobro-Toro JP, Foree B . 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 . February 1980 . 6102916 . 10.1016/0014-2999(80)90072-2 .
4. Kobayashi T, Spande TF, Aoyagi H, Witkop B . Tricyclic analogs of melatonin . Journal of Medicinal Chemistry . 12 . 4 . 636–638 . July 1969 . 5793155 . 10.1021/jm00304a017 .