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Chemical Compound Review

Nitrotoluenos     1-methyl-4-nitro-benzene

Synonyms: p-Nitrotoluene, LS-5, CPD-701, SureCN73252, CHEMBL155320, ...
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Disease relevance of p-Nitrotoluene


High impact information on p-Nitrotoluene


Chemical compound and disease context of p-Nitrotoluene


Biological context of p-Nitrotoluene

  • The substrate specificity of the enzyme expressed from the cloned and overexpressed gene was similar to the activity expressed from strain TW3 grown on 4-nitrotoluene, providing evidence that ntnD is the previously unidentified gene in the pathway of 4-nitrotoluene catabolism [9].
  • Methylation of reduced avian lyase with 1 mM 4-methylnitrobenzene sulfonate results in rapid inactivation of the enzyme with a k(inact) of 0.178 min-1 [10].
  • To address this, we examined the effects of p-nitrotoluene, an endocrine disruptor, on rat behavior and gene expression [11].
  • Inhibition of enterohepatic circulation by bile duct cannulation resulted in a decrease in hepatic macromolecular covalent binding by 98, 75, and 78% in male rats, and by 85, 44, and 45% in female rats after 2NT, 3NT, or 4NT, respectively.(ABSTRACT TRUNCATED AT 250 WORDS)[12]
  • 4-Nitrotoluene (4-NT) was administered orally at doses of 0, 40, 80, or 160 mg/kg/day by gavage to 24 Crj:CD (SD)IGS rats of each sex per group over two successive generations, and the effects on reproductive capacity in the parental animals and growth and development of the offspring were investigated [3].

Anatomical context of p-Nitrotoluene

  • Hepatocytes were incubated with [U-14C]2NT, 3NT, or 4NT at concentrations from 25 to 1000 microM for up to 60 min [13].
  • Kidney toxicity was observed in male rats receiving o-, m-, or p-nitrotoluene and included hyaline droplet nephropathy and an associated increase in the renal concentration of alpha 2U-globulin [14].

Associations of p-Nitrotoluene with other chemical compounds


  1. In vivo construction of a hybrid pathway for metabolism of 4-nitrotoluene in Pseudomonas fluorescens. Michán, C., Delgado, A., Haïdour, A., Lucchesi, G., Ramos, J.L. J. Bacteriol. (1997) [Pubmed]
  2. Reactions involved in the lower pathway for degradation of 4-nitrotoluene by Mycobacterium strain HL 4-NT-1. He, Z., Spain, J.C. Appl. Environ. Microbiol. (2000) [Pubmed]
  3. A two-generation reproductive toxicity study of 4-nitrotoluene in rats. Aso, S., Miyata, K., Ehara, H., Hosyuyama, S., Shiraishi, K., Umano, T., Minobe, Y. The Journal of toxicological sciences. (2005) [Pubmed]
  4. Influence of intestinal bacteria, sex of the animal, and position of the nitro group on the hepatic genotoxicity of nitrotoluene isomers in vivo. Doolittle, D.J., Sherrill, J.M., Butterworth, B.E. Cancer Res. (1983) [Pubmed]
  5. Photocatalytic formation of a carbamate through ethanol-assisted carbonylation of p-nitrotoluene. Maldotti, A., Amadelli, R., Samiolo, L., Molinari, A., Penoni, A., Tollari, S., Cenini, S. Chem. Commun. (Camb.) (2005) [Pubmed]
  6. Accumulation of 2-aminophenoxazin-3-one-7-carboxylate during growth of Pseudomonas putida TW3 on 4-nitro-substituted substrates requires 4-hydroxylaminobenzoate lyase (PnbB). Hughes, M.A., Baggs, M.J., Al-Dulayymi, J., Baird, M.S., Williams, P.A. Appl. Environ. Microbiol. (2002) [Pubmed]
  7. ntn genes determining the early steps in the divergent catabolism of 4-nitrotoluene and toluene in Pseudomonas sp. strain TW3. James, K.D., Williams, P.A. J. Bacteriol. (1998) [Pubmed]
  8. Identification of a hydride-Meisenheimer complex as a metabolite of 2,4,6-trinitrotoluene by a Mycobacterium strain. Vorbeck, C., Lenke, H., Fischer, P., Knackmuss, H.J. J. Bacteriol. (1994) [Pubmed]
  9. Cloning and expression of ntnD, encoding a novel NAD(P)(+)-independent 4-nitrobenzyl alcohol dehydrogenase from Pseudomonas sp. Strain TW3. James, K.D., Hughes, M.A., Williams, P.A. J. Bacteriol. (2000) [Pubmed]
  10. Avian 3-hydroxy-3-methylglutaryl-CoA lyase: sensitivity of enzyme activity to thiol/disulfide exchange and identification of proximal reactive cysteines. Hruz, P.W., Miziorko, H.M. Protein Sci. (1992) [Pubmed]
  11. p-Nitrotoluene causes hyperactivity in the rat. Ishido, M., Masuo, Y., Oka, S., Niki, E., Morita, M. Neurosci. Lett. (2004) [Pubmed]
  12. Isomer- and sex-specific bioactivation of mononitrotoluenes. Role of enterohepatic circulation. Chism, J.P., Rickert, D.E. Drug Metab. Dispos. (1985) [Pubmed]
  13. Metabolism of nitrotoluenes by freshly isolated Fischer 344 rat hepatocytes. deBethizy, J.D., Rickert, D.E. Drug Metab. Dispos. (1984) [Pubmed]
  14. Comparative toxicities of o-, m-, and p-nitrotoluene in 13-week feed studies in F344 rats and B6C3F1 mice. Dunnick, J.K., Elwell, M.R., Bucher, J.R. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1994) [Pubmed]
  15. Efficient quenching of photoluminescence from functionalized single-walled carbon nanotubes by nitroaromatic molecules. Kose, M.E., Harruff, B.A., Lin, Y., Veca, L.M., Lu, F., Sun, Y.P. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2006) [Pubmed]
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