Isolation and structure elucidation of novel products of the acidic degradation of diazepam.
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.
Nudelman
N S
NS
Depto. Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
de Waisbaum
R G
RG
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
D003975:Diazepam