8132. Remoxipride
Nomenclature
CAS number: 80125-14-0
3-Bromo-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2,6-dimethoxybenzamide; (-)-N-ethyl-2-(3-bromo-2,6-dimethoxybenzamidomethyl)pyrrolidine. C16H23BrN2O3; mol wt 371.27.
C 51.76%, H 6.24%, Br 21.52%, N 7.55%, O 12.93%.
Description and references
Specific dopamine D2-receptor antagonist. Prepn: G. L. Florvall, S. O. Ogren, EP 4831; eidem, US 4232037 (1979, 1980 both to Astra); eidem, J. Med. Chem. 25, 1280 (1982). Antidopaminergic activity: S. O. Ogren et al., Eur. J. Pharmacol. 102, 459 (1984). Radiometric determn in urine: A. C. Veltkamp et al., J. Chromatogr. 384, 357 (1987). Clinical pharmacology and pharmacokinetics: L. Farde et al., Psychopharmacology 95, 157 (1988). Clinical evaluation in tardive dyskinesia: U. Andersson et al., ibid. 94, 167 (1988); in schizophrenia: R. G. McCreadie et al., Acta Psychiatr. Scand. 78, 49 (1988).
Properties
[α]D20 -64° (c = 2 in ethanol).Derivative
Hydrochloride monohydrate.Nomenclature
CAS number: 117591-79-4;
73220-03-8
A-33547; FLA-731; Roxiam (Astra). C16H23BrN2O3.HCl.H2O; mol wt 425.75.
C 45.14%, H 6.16%, Br 18.77%, N 6.58%, O 15.03%, Cl 8.33%.
Properties
White to off-white crystalline solid. Loss of water at 105°; mp 173°. [α]D20 -11° (c = 2 in water). pKa 8.9. uv max in water, ethanol, 0.1N HCl: 286, 287, 286 nm (ε 2280, 2260, 2280). Soly (mg/ml): water 300; ethanol 400; dichloromethane 80; acetone 20. LD50 i.p. in rats: 794 μmol/kg (Florvall, Ogren, 1982).Therapeutic Category
Antipsychotic.
Keywords
Antipsychotic; Benzamides; Dopamine Receptor Antagonist