6446. Nemonapride

Nomenclature

CAS number: 75272-39-8
rel-5-Chloro-2-methoxy-4-(methylamino)-N-[(2R,3R)-2-methyl-2-(phenylmethyl)-3-pyrrolidinyl]benzamide; (±)-cis-N-(1-benzyl-2-methyl-3-pyrrolidinyl)-5-chloro-4-(methylamino)-o-anisamide; cis-N-(1-benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino)benzamide; emonapride; YM-09151-2; Emilace (Yamanouchi).
C21H26ClN3O2; mol wt 387.90.
C 65.02%, H 6.76%, Cl 9.14%, N 10.83%, O 8.25%.

Description and references

Selective dopamine D2 receptor antagonist. Prepn: M. Takashima et al., JP Kokai 79 14965; eidem, US 4210660 (1979, 1980 both to Yamanouchi); S. Iwanami et al., J. Med. Chem. 24, 1224 (1981). Pharmacology: M. Yamamoto et al., Neuropharmacology 21, 945 (1982). Dopamine receptor binding study: C. W. Grewe et al., Eur. J. Pharmacol. 81, 149 (1982). Use as a label for D2 receptors: A. S. Unis et al., Life Sci. 47, PL151 (1990). HPLC determn in plasma: T. Nagasaki et al., J. Chromatogr. B 714, 293 (1998). Clinical evaluation in schizophrenia: K. Satoh et al., Int. Clin. Psychopharmacol. 11, 279 (1996).

Chemical structure

Properties

Colorless crystals from isopropanol, mp 152-153° (Takashima, 1980). Also reported as mp 150° (Iwanami).

Therapeutic Category

Antipsychotic.

Keywords

Antipsychotic; Benzamides; Dopamine Receptor Antagonist