Toluene 2,6-dinitro-4-hydroxylamino

Haidour and Ramos (1996) analyzed the degradation products of 2,4,6-trinitrotoluene, 2,4-dinitrotoluene, and 2,6-dinitrotoluene by the bacterium Pseudomonas sp. clone A under aerobic conditions. The bacterium utilized 2,6-dinitrotoluene as a source of nitrogen yielding two compounds 2-amino-6-toluene and 6,6 -dinitro-2,2 -azoxytoluene. 2-Hydroxylamino-6-nitro-toluene and subsequent formation of 2,6-dihydroxyaminotoluene were reported as intermediate products of 2,6-dinitrotoluene metabolism by Clostridium acetobutylicum. 2,6-Diaminotoluene was reported as the end product (Hughes et al., 1999). 

In addition to the compds in Table 1, they obtained evidence for 2-hydroxylamino4,6-dinitro-toluene, 2,4-diamino-6-nitrotoluene, 2,6-diamino-4-nitrotoluene, 2,4,6-trinitrobenzoic acid and (with considerable lack of confidence) 2,4,6-tri-nitrobenzyl alcohol. They confirmed that 2,2 6,6,-tetranitro4,4f azoxytoluene is not a constituent of fresh urine, but may form from 4-hydroxylamino-2,6-dinitrotoluene when the urine is allowed to stand or during isolation procedures. They saw almost no unmetabolized TNT in urine. The urine of orally dosed rats and mice had a bright red color, but not that of dogs and rabbits. The radioactivity of labeled TNT was mainly excreted, but some ended up distributed in various organs... 

Among metabolites in humans the following were identified 4-amino- and 6-aminodinitroioIuene, letranitroazoxy toluene, 2-hydroxylamino-4,6-dinitro-toluene, 2,4-diamino-6-nitro- and 2,6-diamino-4-nitrotoluenc, 2,4,6-trinitro-benzoic acid. A former finding that TNT is toxic to fish has been confirmed. 

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