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Chemical Compound Review

Nitrometan     nitromethane

Synonyms: Nitrocarbol, NITROMETHANE, nitro-methane, NSC-428, NSC428, ...
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Disease relevance of nitromethane


High impact information on nitromethane

  • For synthesis of the AM2 analogue, novel routes via addition of nitromethane followed by conversion of the nitro function to either amino or carboxyl groups were developed [6].
  • Enantioselective Michael additions of nitromethane by a catalytic double activation method using chiral lewis Acid and achiral amine catalysts [7].
  • Condensation of N6-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde with nitromethane followed by acid catalyzed acetylation and borohydride reduction leads to N6-benzoyl-9-(5,6-dideoxy-2,3-O-isopropylidene-6-nitro-beta-D-ribo-hexofuranosyl)adenine (4) [8].
  • We found that upon UV irradiation (> 300 nm) KN photoreduces oxygen to superoxide radical (in DMSO) and nitromethane (CH3NO2) to a nitromethane radical anion (CH3NO2.-) (in air-free buffers, pH 7 and 9.5) [9].
  • The problem of finding a suitable electroosmotic flow marker at low pH in acetonitrile is addressed, and nitromethane is shown to be a proper marker compound under such extreme conditions [10].

Chemical compound and disease context of nitromethane


Biological context of nitromethane


Anatomical context of nitromethane


Associations of nitromethane with other chemical compounds

  • The condensation reaction has been shown (nuclear magnetic resonance) to occur through addition of the methylene carbon of the nitromethane anion to the 4a position of Flox+Et [18].
  • L-phenylalanine ammonia-lyase (maize, potato, and Rhodotorula glutinis). Studies of the prosthetic group with nitromethane [19].
  • It has been found that the intermediate primary nitro Michael adduct can be prepared in a single step by sonication of a mixture of an arylaldehyde, nitromethane, and the 6-aminopyrimidine in acetic acid containing ammonium acetate [20].
  • Cinchona alkaloid-derived chiral bifunctional thiourea organocatalysts were synthesized and applied in the Michael addition between nitromethane and chalcones with high ee and chemical yields [21].
  • They are low-spin hexacoordinated myoglobin or hemoglobin complexes, as shown by the resonance Raman spectrum of the nitromethane-derived human hemoglobin complex which is similar to those of the known hemoglobin complexes with O2, CO, NO and nitrosobenzene [22].

Gene context of nitromethane

  • Histidase activity was approximately 90% inhibited in rats receiving nitromethane [23].
  • The analytic atom-atom intermolecular potential has been successfully regressed by using the MP2/6-31++G**//B3LYP/6-31++G** calculated interaction energies of nitromethane dimer [24].
  • METHODS: A series of 3-aminoacyl-1-aryl-3-methyltriazenes was synthesised through reaction of 1-aryl-3-methyltriazenes with N-BOC protected amino acids using the DCC method of activation, followed by deprotection of the amino function using HCl in nitromethane [25].
  • Male 3-month-old Wistar rats dosed i.p. with 200 mg/kg of nitromethane or -ethane showed increased acid proteinase activity in the brain 4 h after the injection [16].
  • The nitromethane is located in the alpha-CD cavity in an orientation parallel to the plane of the macrocycle, and assumes two sites of equal population with the nitro group in excessive thermal motion; the guest is held by van der Waals contacts and C-H...O-type hydrogen bonds to the pyranose H-3 and H-5 protons [15].

Analytical, diagnostic and therapeutic context of nitromethane


  1. False elevation of serum creatinine following skin absorption of nitromethane complicates the clinical diagnosis of rhabdomyolysis. Gabrielli, A., Hammett-Stabler, C. Chest (1998) [Pubmed]
  2. Molecular electron affinities and the calculation of the temperature dependence of the electron-capture detector response. Chen, E.C., Chen, E.S. Journal of chromatography. A. (2004) [Pubmed]
  3. Peripheral neuropathy in workers exposed to nitromethane. Page, E.H., Pajeau, A.K., Arnold, T.C., Fincher, A.R., Goddard, M.J. Am. J. Ind. Med. (2001) [Pubmed]
  4. Motor dysfunction following chronic exposure to a fluoroalkane solvent mixture containing nitromethane. Sandyk, R., Gillman, M.A. Eur. Neurol. (1984) [Pubmed]
  5. Occupational allergic contact dermatitis to nitromethane. Webb, K.G., Fowler, J.F. Am. J. Contact Dermatitis (2002) [Pubmed]
  6. Synthesis and properties of RNA analogues having amides as interuridine linkages at selected positions. Rozners, E., Katkevica, D., Bizdena, E., Strömberg, R. J. Am. Chem. Soc. (2003) [Pubmed]
  7. Enantioselective Michael additions of nitromethane by a catalytic double activation method using chiral lewis Acid and achiral amine catalysts. Itoh, K., Kanemasa, S. J. Am. Chem. Soc. (2002) [Pubmed]
  8. An approach to the total synthesis of sinefungin. Mock, G.A., Moffatt, J.G. Nucleic Acids Res. (1982) [Pubmed]
  9. Free radical reactions photosensitized by the human lens component, kynurenine: an EPR and spin trapping investigation. Reszka, K.J., Bilski, P., Chignell, C.F., Dillon, J. Free Radic. Biol. Med. (1996) [Pubmed]
  10. Capillary zone electrophoresis of some extremely weak bases in acetonitrile. Porras, S.P. Anal. Chem. (2006) [Pubmed]
  11. Subchronic inhalation toxicity of nitromethane and 2-nitropropane. Lewis, T.R., Ulrich, C.E., Busey, W.M. Journal of environmental pathology and toxicology. (1979) [Pubmed]
  12. Stereoselective and efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol. Quaedflieg, P.J., Kesteleyn, B.R., Wigerinck, P.B., Goyvaerts, N.M., Vijn, R.J., Liebregts, C.S., Kooistra, J.H., Cusan, C. Org. Lett. (2005) [Pubmed]
  13. Synthesis of novel retinoid X receptor-selective retinoids. Faul, M.M., Ratz, A.M., Sullivan, K.A., Trankle, W.G., Winneroski, L.L. J. Org. Chem. (2001) [Pubmed]
  14. The utility of the guppy (Poecilia reticulata) and medaka (Oryzias latipes) in evaluation of chemicals for carcinogenicity. Kissling, G.E., Bernheim, N.J., Hawkins, W.E., Wolfe, M.J., Jokinen, M.P., Smith, C.S., Herbert, R.A., Boorman, G.A. Toxicol. Sci. (2006) [Pubmed]
  15. Topography of the 1:1 alpha-cyclodextrin-nitromethane inclusion complex. Nakagawa, T., Immel, S., Lichtenthaler, F.W., Lindner, H.J. Carbohydr. Res. (2000) [Pubmed]
  16. Comparison of acute toxic effects of intraperitoneally injected nitromethane and nitroethane in rats. Zitting, A., Nickels, J., Savolainen, H. Toxicol. Lett. (1982) [Pubmed]
  17. Surface-initiated atom transfer radical polymerization on poly(vinylidene fluoride) membrane for antibacterial ability. Zhai, G., Shi, Z.L., Kang, E.T., Neoh, K.G. Macromolecular bioscience. (2005) [Pubmed]
  18. Importance of C4a- and N5-covalent adducts in the flavin oxidation of carbanions. Chan, T.W., Bruice, T.C. Biochemistry (1978) [Pubmed]
  19. L-phenylalanine ammonia-lyase (maize, potato, and Rhodotorula glutinis). Studies of the prosthetic group with nitromethane. Havir, E.A., Hanson, K.R. Biochemistry (1975) [Pubmed]
  20. A new and efficient synthesis of pyrrolo[2,3-d]pyrimidine anticancer agents: Alimta (LY231514, MTA), homo-Alimta, TNP-351, and some aryl 5-substituted pyrrolo[2,3-d]pyrimidines. Taylor, E.C., Liu, B. J. Org. Chem. (2003) [Pubmed]
  21. Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts. Vakulya, B., Varga, S., Csámpai, A., Soós, T. Org. Lett. (2005) [Pubmed]
  22. Nitrosoalkanes as Fe(II) ligands in the hemoglobin and myoglobin complexes formed from nitroalkanes in reducing conditions. Mansuy, D., Chottard, J.C., Chottard, G. Eur. J. Biochem. (1977) [Pubmed]
  23. Reduced locomotor activity of rats made histidinemic by injection of histidine. Dutra-Filho, C.S., Wannmacher, C.M., Pires, R.F., Gus, G., Kalil, A.M., Wajner, M. J. Nutr. (1989) [Pubmed]
  24. An ab initio study of intermolecular interactions of nitromethane dimer and nitromethane trimer. Li, J., Zhao, F., Jing, F. Journal of computational chemistry. (2003) [Pubmed]
  25. Triazene drug metabolites: part 15. Synthesis and plasma hydrolysis of anticancer triazenes containing amino acid carriers. Carvalho, E., Iley, J., Perry, M.J., Rosa, E. Pharm. Res. (1998) [Pubmed]
  26. Nitromethane as solvent in capillary electrophoresis. Subirats, X., Porras, S.P., Rosés, M., Kenndler, E. Journal of chromatography. A. (2005) [Pubmed]
  27. High-performance liquid chromatographic separation of polycyclic aromatic hydrocarbons using pyridinium chloride as a selective fluorescence quencher to aid detection. Mao, C., Tucker, S.A. Journal of chromatography. A. (2002) [Pubmed]
  28. Kinetic insights into the role of the solvent in the polymorphism of 5-fluorouracil from molecular dynamics simulations. Hamad, S., Moon, C., Catlow, C.R., Hulme, A.T., Price, S.L. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2006) [Pubmed]
  29. Forensic analysis of commercial petroleum products using selective fluorescence quenching. Goodpaster, J.V., Howerton, S.B., McGuffin, L. J. Forensic Sci. (2001) [Pubmed]
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