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Chemical Compound Review

NITROTOLUENE     1-methyl-2-nitro-benzene

Synonyms: o-NT, o-Nitrotoluol, O-NITROTOLUENE, CHEMBL47047, SureCN26788, ...
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Disease relevance of o-Methylnitrobenzene


High impact information on o-Methylnitrobenzene

  • When F344 females with conventional intestinal microflora were gavaged with 2NT and primary hepatocyte cultures were prepared, no unscheduled DNA synthesis was observed (200 mg/kg: -2.6 NG) [5].
  • 2NT did not induce DNA repair in germ-free animals (200 mg/kg: -3.8 NG), whereas DNA repair was induced in Charles River Altered Schaedler Flora-associated animals (200 mg/kg: 5.4 NG) [5].
  • These results demonstrate that the mononitrotoluenes display marked isomeric differences in their genotoxic potential, indicate the obligatory role of intestinal bacteria in the metabolic activation of 2NT, and show that the genotoxic potential of 2NT is dependent upon the sex of the animal under study [5].
  • Twenty-four hr following treatment with 2NT, a 50-fold increase in the number of hepatocytes in S phase was observed and indicated that 2NT induces cell division in addition to DNA repair [5].
  • The recently completed o-nitrotoluene study provided the first cecal tumor response and an opportunity to evaluate the morphology and molecular profile of oncogenes and tumor suppressor genes that are relevant to humans [1].

Chemical compound and disease context of o-Methylnitrobenzene


Biological context of o-Methylnitrobenzene


Anatomical context of o-Methylnitrobenzene


Associations of o-Methylnitrobenzene with other chemical compounds


Gene context of o-Methylnitrobenzene


Analytical, diagnostic and therapeutic context of o-Methylnitrobenzene


  1. o-Nitrotoluene-induced large intestinal tumors in B6C3F1 mice model human colon cancer in their molecular pathogenesis. Sills, R.C., Hong, H.L., Flake, G., Moomaw, C., Clayton, N., Boorman, G.A., Dunnick, J., Devereux, T.R. Carcinogenesis (2004) [Pubmed]
  2. Cloning and sequencing of the genes encoding 2-nitrotoluene dioxygenase from Pseudomonas sp. JS42. Parales, J.V., Kumar, A., Parales, R.E., Gibson, D.T. Gene (1996) [Pubmed]
  3. Purification, characterization, and crystallization of the components of the nitrobenzene and 2-nitrotoluene dioxygenase enzyme systems. Parales, R.E., Huang, R., Yu, C.L., Parales, J.V., Lee, F.K., Lessner, D.J., Ivkovic-Jensen, M.M., Liu, W., Friemann, R., Ramaswamy, S., Gibson, D.T. Appl. Environ. Microbiol. (2005) [Pubmed]
  4. Chemical-specific alterations in ras, p53, and beta-catenin genes in hemangiosarcomas from B6C3F1 mice exposed to o-nitrotoluene or riddelliine for 2 years. Hong, H.L., Ton, T.V., Devereux, T.R., Moomaw, C., Clayton, N., Chan, P., Dunnick, J.K., Sills, R.C. Toxicol. Appl. Pharmacol. (2003) [Pubmed]
  5. 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]
  6. Biodegradation of 2-nitrotoluene by Pseudomonas sp. strain JS42. Haigler, B.E., Wallace, W.H., Spain, J.C. Appl. Environ. Microbiol. (1994) [Pubmed]
  7. Oxidative release of nitrite from 2-nitrotoluene by a three-component enzyme system from Pseudomonas sp. strain JS42. An, D., Gibson, D.T., Spain, J.C. J. Bacteriol. (1994) [Pubmed]
  8. Molecular characterization and substrate specificity of nitrobenzene dioxygenase from Comamonas sp. strain JS765. Lessner, D.J., Johnson, G.R., Parales, R.E., Spain, J.C., Gibson, D.T. Appl. Environ. Microbiol. (2002) [Pubmed]
  9. (+/-)-4-Aryl-4,5-dihydro-3H-1,3-benzodiazepines. 2. Nuclear-substituted analogues of (+/-)-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine and (+/-)-4,5-dihydro-2-ethyl-3-methyl-4-phenyl-3H-1,3-benzodiazepine as potential antidepressant agents. Martin, L.L., Setescak, L.L., Worm, M., Crichlow, C.A., Geyer, H.M., Wilker, J.C. J. Med. Chem. (1982) [Pubmed]
  10. A computational study on the kinetics and mechanism for the unimolecular decomposition of o-nitrotoluene. Chen, S.C., Xu, S.C., Diau, E., Lin, M.C. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  11. Major carcinogenic pathways identified by gene expression analysis of peritoneal mesotheliomas following chemical treatment in F344 rats. Kim, Y., Ton, T.V., DeAngelo, A.B., Morgan, K., Devereux, T.R., Anna, C., Collins, J.B., Paules, R.S., Crosby, L.M., Sills, R.C. Toxicol. Appl. Pharmacol. (2006) [Pubmed]
  12. Active site residues controlling substrate specificity in 2-nitrotoluene dioxygenase from Acidovorax sp. strain JS42. Lee, K.S., Parales, J.V., Friemann, R., Parales, R.E. J. Ind. Microbiol. Biotechnol. (2005) [Pubmed]
  13. Carcinogenic potential of o-nitrotoluene and p-nitrotoluene. Dunnick, J.K., Burka, L.T., Mahler, J., Sills, R. Toxicology (2003) [Pubmed]
  14. Biomarkers of exposure, effect, and susceptibility in workers exposed to nitrotoluenes. Sabbioni, G., Jones, C.R., Sepai, O., Hirvonen, A., Norppa, H., Järventaus, H., Glatt, H., Pomplun, D., Yan, H., Brooks, L.R., Warren, S.H., Demarini, D.M., Liu, Y.Y. Cancer Epidemiol. Biomarkers Prev. (2006) [Pubmed]
  15. Urinary metabolites of workers exposed to nitrotoluenes. Jones, C.R., Sepai, O., Liu, Y.Y., Yan, H., Sabbioni, G. Biomarkers (2005) [Pubmed]
  16. 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]
  17. Application of a picrolonate ion-selective electrode to the assay of calcium and piperazine in pharmaceuticals and serum. Veltsistas, P.G., Prodromidis, M.I., Karayannis, M.I. The Analyst. (1994) [Pubmed]
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