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 charac...

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Veröffentlicht in:Journal of pharmaceutical sciences 1995-02, Vol.84 (2), p.208-211
Hauptverfasser: Sbarbati Nudelman, N., de Waisbaum, R.G.
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3549
1520-6017
DOI:10.1002/jps.2600840217