Abstract
Four rat urinary metabolites of chlordiazepoxide (7-chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine 4-oxide) labeled at C-2 with 14C were separated by solvent extraction and thin-layer chromatography (TLC) and characterized by high resolution mass spectrometry. Each metabolite was found to have a hydroxyl function in the C-5 phenyl ring, and two-dimensional TLC of metabolites with reference compounds indicated that the most probable location of the phenolic function was para to the diazepine ring. The four metabolites were: 7-chloro-1,3-dihydro-5-(4-hydroxyphenyl)-2H-1,4-benzodiazepin-2-one 4-oxide (Metabolite 1); 2-amino-7-chloro-5-(4-hydroxyphenyl)-3H-1,4-benzodiazepine 4-oxide (Metabolite 2); 7-chloro-5-(4-hydroxyphenyl)-2-mwthylamino-3H-1,4-benzodiazepine 4-oxide (Metabolite 3); and 7-chloro-1,3-dihydro5-(4-hydroxyphenyl)-2H-1,4-benzodiazepin-2-one (Metabolite 4), which differs from the others in that it no longer retains the N-oxide function).
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