The metabolism of the trichloronitrobenzenes in the rabbit

Abstract

The metabolism of the six isomeric trichloronitrobenzenes was studied. Considerable amounts of mercapturic acids are formed by all the isomers except 2:4:6-trichloronitrobenzene, of which less than 1% of the dose is converted into mercapturic acid. The mercapturic acids from 2:3:4-, 2:3:5-, 2:4:5- and 3:4:5-trichloronitrobenzenes were formed, in effect, by acetylcysteyldechlorination and were isolated from urine. The mercapturic acids from 2:3:6- and 2:4:6-trichloro-benzene were formed, in effect, by acetylcysteyldenitration, and their presence in urine was shown by isolation of the corresponding hexa-chlorodiphenyl disulfides. All the trichloronitrobenzenes were reduced to the corresponding anilines. Hexachloroazoxybenzenes were isolated from the urine of rabbits dosed with the 2:4:5- and 3:4:5-isomers. All the trichloronitrobenzenes yielded amino-trichlorphenols. Amino-trichlorophenols were isolated from urines of rabbits given 2:3:4-, 2:3:5-, 2:3:6- and 3:4:5-trichloronitrobenzene. The excretion of a trichloronitrophenol was detected after administration of the 2:3:6-, 2:4:5- and 2:4:6-isomers. 4-Amino-3:5-dichlorophenol is a metabolite of 2:4:6-trichloronitrobenzene and 2:4:6-trichloroaniline. It is probably formed by hydroxyldechlorination of the trichloroaniline. 4-Amino-2:5-dichlorophenol is a minor metabolite of 2:4:5-trichloronitrobenzene.