Chemical and Pharmaceutical Bulletin p. 327 - 332 (1985)
Update date:2022-07-30
Topics:
Mori
Kudo
Nunozawa
Miyahara
Kozuka
2,4-Dinitrotoluene (2,4-DNT), which is an industrial chemical of importance in the production of urethane foams and elastomers, is a hepatocarcinogen in rats. 2,4-Diaminotoluene (2,4-DAT), one of the urinary and hepatic metabolites of 2,4-DNT, is also carcinogenic in rats. We have studied the pathways of metabolism of 2,4-DNT in the cecal microflora of rats. 2,4-DNT was not metabolized by this preparation in the presence of oxygen. Under anaerobic conditions, an ordered sequence of reductive metabolism was observed. 2,4-DNT was reduced to 2-amino-4-nitrotoluene (2A4NT) and 4-amino-2-nitrotoluene (4A2NT) via 2-hydroxylamino-4-nitrotoluene (2HA4NT) and 4-hydroxylamino-2-nitrotoluene (4HA2NT), which were identified by mass spectral (MS) comparison with authentic materials. The two aminonitrotoluenes were then reduced to 2,4-DAT. No intermediates in this sequence could be isolated. These findings indicate that rat intestinal microflora catalyze the reductive metabolism of 2,4-DNT and suggest that the reduction of 2,4-DNT to 2,4-DAT may play a role in the carcinogenicity of 2,4-DNT.
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Doi:10.1021/ic701614c
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(1976)
