title: Isolation and structure elucidation of novel products of the acidic degradation of diazepam.
abstract: The acidic degradation of diazepam in methanolic aqueous solution has been investigated. Apart from the known degradation products, 2-(N-methylamino)-5-chlorobenzophenone and glycine, produced by the hydrolytic cleavage of the benzodiazepinone ring, five novel products were isolated and fully characterized by their spectroscopic features and independent synthesis. Substituted 2-amino-3,5-dichlorobenzophenones and 2,4-dichloroacridinones were found, the formation of which in the reaction media is mechanistically intriguing. The role of these unexpected products in accelerated studies of diazepam stability is discussed.
authors.affiliation: Depto. Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
authors.forename: N S
authors.initials: NS
authors.lastname: Nudelman
authors.forename: R G
authors.initials: RG
authors.lastname: de Waisbaum
mesh_terms: D002855:Chromatography, Thin Layer; D003975:Diazepam / Q000737:chemistry*; D004355:Drug Stability; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
chemical_list: D003975:Diazepam