p-クロロアニリン代謝物の尿中への排泄
2,4-ジクロロアニリン, p-クロロホルムアニリドの排泄
1992 年 34 巻 1 号 p. 3-9
詳細
1992 年 34 巻 1 号 p. 3-9
Previously, we identified by gas chromatography/mass spectrometry (GC/MS) urinary metabolites of p-chloroaniline (p-CA) in a patient with acute p-CA poisoning. Among these metabolites there is a possibility that 2, 4-dichloroaniline (2, 4-DCA) and p-chloroformanilide (p-CFA) are produced through some unknown metabolic pathways in human.
In order to clarify whether 2, 4-DCA and p-CFA were produced within the human body or not, an attempt was made to detect these metabolites in the patient's urine samples prepared by various pretreatments, using both GC/MS and high performance liquid chromatograph. In addition, the detection of these metabolites in non-exposed person's urine samples spiked with p-CA and 2-amino-5-chlorophenol was attempted by GC/MS using same the procedures in order to examine whether p-CA and 2-amino-5-chlorophenol excreted as metabolites were further changed to 2, 4-DCA or p-CFA in the urine or not.
2, 4-DCA was found abundantly in the ethereal extracts from the patient's urine samples hydrolyzed with hydrochloric, sulfuric and nitric acids, but only small amounts from intact urine samples by GC/MS. No 2, 4-DCA was detected in the urine samples to which were added p-CA and 2-amino-5-chlorophenol. p-CFA was found in the ethereal samples which were extracted at acidic conditions from the patient's urine samples by GC/MS at the injection port temperature of 250°C of the gas chromatograph, but the p-CFA peak disappeared at the injection port temperature of 150°C. On the other hand, in the urine samples to which were added p-CA, traces of p-CFA were detected by GC/MS in the both injection port temperatures. By high performance liquid chromatography, 2, 4-DCA could be detected in the urine of the patient, but p-CFA could not.
It is considered that 2, 4-DCA was synthesized from p-CA by chlorination pathway in the human body and most of the 2, 4-DCA forming conjugates was excreted into the urine or remained in the urine after binding with urinary components. p-CFA found in patient's urine by GC/MS was considered to have resulted from pyrolysis of a precursor originating from p-CA at the injection port of the gas chromatograph, though a part of p-CA excreted as metabolites was changed to p-CFA in the urine.
