[Identification of urinary metabolites in a patient of acute poisoning by p-chloroaniline].

In order to clarify urinary metabolites of p-chloroaniline (p-CA), urine samples of a patient acutely poisoned with p-CA were analyzed by gas chromatography/mass spectrometry. Urinary metabolites were extracted with diethylether at pH 1.0 and pH 10 from urine samples hydrolyzed with acid and base and from intact urine samples. Aliquots of the ethereal extracts were injected into the gas chromatography, and p-CA and its metabolites were identified by comparing their mass spectra and retention times to those of standards. Six substances identified were as follows: p-CA, 2-amino-5-chlorophenol, 2,4-dichloroaniline, p-chloroformanilide and traces of p-chloroacetanilide and 4-chloro-2-hydroxyacetanilide. Since p-CA was mainly detected in the hydrolyzed urine samples, p-CA was considered to form conjugates in the urine. N-Acetylation reactions of p-CA were suggested to be weak in human, because extremely minute amounts of p-chloroacetanilide and 4-chloro-2-hydroxyacetanilide were detected in the urine.