Remoxipride
Title: Remoxipride
CAS Registry Number: 80125-14-0
CAS Name: 3-Bromo-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2,6-dimethoxybenzamide
Additional Names: (-)-N-ethyl-2-(3-bromo-2,6-dimethoxybenzamidomethyl)pyrrolidine
Molecular Formula: C16H23BrN2O3
Molecular Weight: 371.27
Percent Composition: C 51.76%, H 6.24%, Br 21.52%, N 7.55%, O 12.93%
Literature 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: [a]D20 -64° (c = 2 in ethanol).
Optical Rotation: [a]D20 -64° (c = 2 in ethanol)
 
Derivative Type: Hydrochloride monohydrate
CAS Registry Number: 117591-79-4; 73220-03-8
Manufacturers' Codes: A-33547; FLA-731
Trademarks: Roxiam (Astra)
Molecular Formula: C16H23BrN2O3.HCl.H2O
Molecular Weight: 425.75
Percent Composition: 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°. [a]D20 -11° (c = 2 in water). pKa 8.9. uv max in water, ethanol, 0.1N HCl: 286, 287, 286 nm (e 2280, 2260, 2280). Soly (mg/ml): water 300; ethanol 400; dichloromethane 80; acetone 20. LD50 i.p. in rats: 794 mmol/kg (Florvall, Ogren, 1982).
Melting point: mp 173°
pKa: pKa 8.9
Optical Rotation: [a]D20 -11° (c = 2 in water)
Absorption maximum: uv max in water, ethanol, 0.1N HCl: 286, 287, 286 nm (e 2280, 2260, 2280)
Toxicity data: LD50 i.p. in rats: 794 mmol/kg (Florvall, Ogren, 1982)
 
Therap-Cat: Antipsychotic.
Keywords: Antipsychotic; Benzamides; Dopamine Receptor Antagonist.

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