The metabolism of 2:3:5:6- and 2:3:4:5-tetrachloronitrobenzenes in the rabbit and the reduction of aromatic nitro compounds in the intestine

Abstract

The 2,3,5,6-(I) and 2,3,4,5-(II) tetrachloronitrobenzenes are poorly absorbed, an avg. of 66% and 33%, respectively, being excreted in feces. The avg. percentages of a dose of I excreted in urine as the tetrachloro-aniline, glucuronide, ethereal sulfate and mercapturic acid were 10, 12, 1 and 11, respectively, Some 4-amino-2,3,5,6-tetra-chlorophenol was excreted unconjugated. This metabolite, the tetrachloroaniline and N-acetyl-S-(2,3,5,6-tetrachlorophenyl)-L-cysteine were isolated. M-Hydroxybenzoic acid was isolated from urine after admn. of I. When 2,3,5,6-tetrachloroaniline was given to rabbits, the avg. percentages of the dose excreted unchanged were 18% in feces and 15% in urine, 60% was excreted as the glucuronide and 10% as the ethereal sulfate. No mercapturic acid formation was detected. The avg. percentages of a dose of II excreted in urine as 2,3,4,5-tetrachloroaniline, glucuronide and ethereal sulfate were 13, 46 and 6 respectively. The tetrachloroaniline was isolated as such. No mercapturic acid formation was detected. Various aromatic nitro compounds are reduced by intestinal bacteria.