The metabolism of 2:4-, 2:5- and 3:4-dichloronitrobenzene in the rabbit

Abstract

The metabolism of 2:4-, 2:5-, and 3:4-dichloronitrobenzene was studied in the rabbit. The main products excreted in urine are mercapturic acids (corresponding to 30-50% of the dose) and phenols conjugated with glucuronic and sulfuric acids. Smaller amounts of dichloroanilines are excreted. The mercapturic acids were isolated and their structure was confirmed by synthesis. In each case they are formed by substitution of the labile chlorine atoms. 2-Bromo-4-chloro-, 2-bromo-5-chloro- and 4-bromo-3-chloro-nitrobenzene when fed to rabbits yield the same mercapturic acids as do the corresponding dichloronitrobenzenes. Several of the nitro- and amino-dichlorophenols excreted were identified. 3:4:3[image]:4[image]-Tetrachloroazoxylbenzene was isolated from the urine of rabbits given 3:4-dichloronitrobenzene.