Mutagenicity of urinary metabolites of 2,4-dinitrotoluene to Salmonella typhimurium.

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Abstract
2, 4-Dinitrotoluene (2, 4-DNT) and its urinary metabolites [2-amino-4-nitrotoluene (2A4NT), 4-amino-2-nitrotoluene (4A2NT), 2, 4-diaminotoluene (2, 4-DAT), 2, 4-dinitrobenzyl alcohol (2, 4-DNB), 2-amino-4-nitrobenzyl alcohol (2A4NB), 4-amino-2-nitrobenzyl alcohol (4A2NB), 2-nitro-4-acetylaminotoluene (2N4AAT), 2-amino-4-acetylaminotoluene (2A4AAT), 2-amino-4-acetyl-aminobenzoic acid (2A4AABA) and 2, 4-dinitrobenzoic acid (2, 4-DNBA)] and 2, 4-dinitrobenzal-dehyde (2, 4-DNAl), an intermediate in the oxidation of 2, 4-DNB to 2, 4-DNBA, were tested for mutagenicity in Salmonella typhimurium strains TA 98 and TA 100 in the absence or presence of S9 mix. 2, 4-DNT itself was only a weak mutagen. 2A4NT, 4A2NT, 2N4AAT, 2A4AABA and 2, 4-DNBA were inactive toward strains TA 98 and TA 100 in the absence or presence of S9 mix. In contrast with these metabolites, 2A4AAT, 2A4NB, 4A2NB, 2, 4-DAT, 2, 4-DNB and 2, 4-DNAl were more mutagenic than 2, 4-DNT, being increasingly mutagenic in that order. 2A4AAT, 2A4NB and 4A2NB were weak mutagens at mM concentrations, while 2, 4-DAT, 2, 4-DNB and 2, 4-DNAl were mutagenic at μM concentrations. These results suggest that the metabolic conversion of 2, 4-DNT to 2, 4-DNB, 2, 4-DNAl, and 2, 4-DAT, a known carcinogen, may contribute to the carcinogenicity of 2, 4-DNT.

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