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Chemical Compound Review:

m-Nitrotoluol 1-methyl-3-nitro-benzene

Synonyms: m-Nitrotoluene, SureCN92055, CHEMBL114059, NSC-9578, CCRIS 2312, ...

Burns, L.A. et al., deBethizy, J.D. et al., Neumann, G. et al., Meyer, D. et al.

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Disease relevance of meta-Nitrotoluol

Suitability of recombinant Escherichia coli and Pseudomonas putida strains for selective biotransformation of m-nitrotoluene by xylene monooxygenase [1].
Exposure of mice to m-nitrotoluene decreased resistance to Listeria monocytogenes [2].
Mice, exposed to m-nitrotoluene at dose levels of 200, 400 and 600 mg/kg/body weight for 2 weeks by gastric gavage, gained body weight over the treatment period to a slightly greater extent than the control groups [2].

High impact information on meta-Nitrotoluol

Incubation of 2NT, 3NT, or 4NT (1 mM) with rat hepatic microsomes produced only the respective nitrobenzyl alcohols and the rate of formation was linear for 90 min [3].
2-Nitrotoluene (2NT), but not 3-nitrotoluene (3NT) or 4-nitrotoluene (4NT), is genotoxic in the in vivo-in vitro hepatic DNA repair assay [3].
In the present studies, the toxicology and immunotoxicity of meta-nitrotoluene (m-nitrotoluene) were evaluated [2].
Of the selected organs weighed, the liver and kidney of mice exposed to m-nitrotoluene were increased in weight while the thymus weight was decreased [2].
The hematology and serum chemistries examined were unaffected by m-nitrotoluene exposure although there were modest decreases in the percentage of polymorphonuclear leukocytes and eosinophils in differential blood counts [2].

Biological context of meta-Nitrotoluol

Fc-mediated adherence and phagocytosis of chicken erythrocytes and NK cell activity were increased dose dependently in mice exposed to m-nitrotoluene [2].

Anatomical context of meta-Nitrotoluol

The liver of mice exposed to m-nitrotoluene, but not ortho-nitrotoluene, showed slight to moderate swelling of the hepatocytes adjacent to the central veins [2].
Bone marrow cellularity and the number of CFU/M and CFU/GM were unaffected by m-nitrotoluene exposure. m-Nitrotoluene suppressed the IgM response to sRBC and the DHR response to KLH [2].
Several immune parameters were unaffected by exposure to m-nitrotoluene, including the IgG response to sRBC, responses to the B cell mitogen LPS and to allogeneic cells, and serum interferon levels [2].

Analytical, diagnostic and therapeutic context of meta-Nitrotoluol

Transferring this example to a 5-liter-scale bioreactor with 10% (vol/vol) 1-decanol, the amount of 3-nitrotoluene tolerated by the cells is up to 200-fold higher than in pure aqueous medium [4].

References

Suitability of recombinant Escherichia coli and Pseudomonas putida strains for selective biotransformation of m-nitrotoluene by xylene monooxygenase. Meyer, D., Witholt, B., Schmid, A. Appl. Environ. Microbiol. (2005) [Pubmed]
Immunotoxicity of mono-nitrotoluenes in female B6C3F1 mice: II. Meta-nitrotoluene. Burns, L.A., White, K.L., McCay, J.A., Fuchs, B.A., Stern, M., Brown, R.D., Musgrove, D.L., Holsapple, M.P., Luster, M.I., Bradley, S.G. Drug and chemical toxicology. (1994) [Pubmed]
Metabolism of nitrotoluenes by freshly isolated Fischer 344 rat hepatocytes. deBethizy, J.D., Rickert, D.E. Drug Metab. Dispos. (1984) [Pubmed]
Prediction of the adaptability of Pseudomonas putida DOT-T1E to a second phase of a solvent for economically sound two-phase biotransformations. Neumann, G., Kabelitz, N., Zehnsdorf, A., Miltner, A., Lippold, H., Meyer, D., Schmid, A., Heipieper, H.J. Appl. Environ. Microbiol. (2005) [Pubmed]

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