Summary: Alkanes having one or more nitro (NO2) groups attached to carbon atoms.

Top Publications

  1. Zhou J, Mao H, Wang L, Zou J, Zhang W. Lithium perchlorate-nitromethane-promoted alkylation of anilines with arylmethanols. Mol Divers. 2011;15:849-55 pubmed publisher
    ..This method does not require the use of transition metal catalysts to prepare alkylated aniline derivatives. ..
  2. Miura T, Kim S, Kitano Y, Tada M, Chiba K. Electrochemical enol ether/olefin cross-metathesis in a lithium perchlorate/nitromethane electrolyte solution. Angew Chem Int Ed Engl. 2006;45:1461-3 pubmed
  3. Muthusamy M, Ambundo E, George S, Lippard S, Thorneley R. Stopped-flow Fourier transform infrared spectroscopy of nitromethane oxidation by the diiron(IV) intermediate of methane monooxygenase. J Am Chem Soc. 2003;125:11150-1 pubmed
    ..These results provide for the first time direct monitoring of the hydroxylation of a methane-derived substrate in the MMOH reaction pathway and demonstrate that Q decay occurs concomitantly with substrate consumption. ..
  4. Leinisch F, Jiang J, Deterding L, Mason R. Simplified synthesis of isotopically labeled 5,5-dimethyl-pyrroline N-oxide. Molecules. 2011;16:8428-36 pubmed publisher
    ..This facile, straightforward process allows synthesizing isotopically labeled DMPO analogs in a 4-step reaction without special equipment. ..
  5. Boutros J, Bayachou M. Myoglobin as an efficient electrocatalyst for nitromethane reduction. Inorg Chem. 2004;43:3847-53 pubmed
    ..A rationale for the catalysis invokes the highly reduced Fe(I) state of myoglobin in surfactant film; the latter engages in efficient inner-sphere electron transfers to the nitro compound coupled to proton transfers. ..
  6. Rais J, Okada T, Alexova J. Gibbs energies of transfer of alkali metal cations between mutually saturated water-solvent systems determined from extraction experiments with radiotracer 137Cs. J Phys Chem B. 2006;110:8432-40 pubmed
  7. Ferreira da Silva F, Ptasinska S, Denifl S, Gschliesser D, Postler J, Matias C, et al. Electron interaction with nitromethane embedded in helium droplets: attachment and ionization measurements. J Chem Phys. 2011;135:174504 pubmed publisher
  8. Walvoord R, Berritt S, Kozlowski M. Palladium-catalyzed nitromethylation of aryl halides: an orthogonal formylation equivalent. Org Lett. 2012;14:4086-9 pubmed publisher
    ..The process exploits inexpensive nitromethane as a carbonyl equivalent, providing a mild and convenient formylation method that is compatible with many functional groups. ..
  9. Fuhshuku K, Asano Y. Synthesis of (R)-?-nitro alcohols catalyzed by R-selective hydroxynitrile lyase from Arabidopsis thaliana in the aqueous-organic biphasic system. J Biotechnol. 2011;153:153-9 pubmed publisher
    ..The organic solvent giving the highest enantioselectivity was n-butyl acetate (AcOBu) with an optimum aqueous phase content of 50% (v/v). This is the first example of the R-HNL-catalyzed synthesis of (R)-?-nitro alcohols. ..

More Information


  1. DeMatos L, Williams A, Booth S, Petts C, Taylor D, Blagden N. Solvent influences on metastable polymorph lifetimes: real-time interconversions using energy dispersive X-ray diffractometry. J Pharm Sci. 2007;96:1069-78 pubmed
  2. Palomo C, Landa A, Mielgo A, Oiarbide M, Puente A, Vera S. Water-compatible iminium activation: organocatalytic Michael reactions of carbon-centered nucleophiles with enals. Angew Chem Int Ed Engl. 2007;46:8431-5 pubmed
  3. Casalini C, Lodovici M, Briani C, Paganelli G, Remy S, Cheynier V, et al. Effect of complex polyphenols and tannins from red wine (WCPT) on chemically induced oxidative DNA damage in the rat. Eur J Nutr. 1999;38:190-5 pubmed
    ..2NP and DMH are hepatic and colon carcinogens, respectively, capable of inducing oxidative DNA damage. WCPT have protective action against some types of chemically-induced oxidative DNA damage in vivo. ..
  4. Beier R, Anderson R, Krueger N, Edrington T, Callaway T, Nisbet D. Effect of nitroethane and nitroethanol on the production of indole and 3-methylindole (skatole) from bacteria in swine feces by gas chromatography. J Environ Sci Health B. 2009;44:613-20 pubmed publisher
    ..0% (P = 0.02) and 23.5% skatole production, respectively, and a decrease of 14.9% indole at 6 h, but an increase in indole production of 81.1% at 24 h. ..
  5. Wentworth A, Yiannias J, Keeling J, Hall M, Camilleri M, Drage L, et al. Trends in patch-test results and allergen changes in the standard series: a Mayo Clinic 5-year retrospective review (January 1, 2006, to December 31, 2010). J Am Acad Dermatol. 2014;70:269-75.e4 pubmed publisher
    ..Patch testing is essential for identification of culprits causing allergic contact dermatitis...
  6. Saengkerdsub S, Kim W, Anderson R, Nisbet D, Ricke S. Effects of nitro compounds and feedstuffs on in vitro methane production in chicken cecal contents and rumen fluid. Anaerobe. 2006;12:85-92 pubmed
    ..Unlike cecal contents, LF significantly (P<0.05) supported in vitro methane production in incubations of both rumen fluids. The results show that NE impedes methane production, especially in incubations of chicken cecal contents. ..
  7. Schoeps K, Langstrom B, Stone Elander S, Halldin C. Synthesis of [1-11C]D-glucose and [1-11C]D-mannose from on-line produced [11C]nitromethane. Int J Rad Appl Instrum A. 1991;42:877-83 pubmed
    ..Compounds III and IV were isolated using semi-preparative HPLC and the radiochemical purity was greater than 97%. In a typical run, 1.5-2.0 mCi of III and 6-8 mCi of IV could be isolated (starting from 70-90 mCi [11C]nitromethane). ..
  8. Borges L, Nogueira C, Panatieri R, Rocha J, Zeni G. Acute liver damage induced by 2-nitropropane in rats: effect of diphenyl diselenide on antioxidant defenses. Chem Biol Interact. 2006;160:99-107 pubmed
    ..This study points out the involvement of CAT activity in 2-NP-induced acute liver damage and suggests that the post-treatment with diphenyl diselenide was effective in restoring the hepatic damage induced by 2-NP. ..
  9. Wilhelm E, Jesse C, Nogueira C, Savegnago L. Introduction of trifluoromethyl group into diphenyl diselenide molecule alters its toxicity and protective effect against damage induced by 2-nitropropane in rats. Exp Toxicol Pathol. 2009;61:197-203 pubmed publisher
    ..These results indicate that the chemical alteration into (PhSe)(2) molecule introduced toxicity and altered its protective effect against damage induced by 2-NP in rats. ..
  10. Simon K, Mukundan A, Dewundara S, Van Remmen H, Dombkowski A, Cabelof D. Transcriptional profiling of the age-related response to genotoxic stress points to differential DNA damage response with age. Mech Ageing Dev. 2009;130:637-47 pubmed publisher
    ..Expression data is consistent with loss of apoptosis following DNA damage in old animals. These data suggest DNA damage responses differ greatly in young and old animals. ..
  11. Gobin C, Marteau P, Petitet J. Spectroscopic studies of the molecular interactions in n-ethylamines and 2-nitropropane/n-ethylamine mixtures. Spectrochim Acta A Mol Biomol Spectrosc. 2004;60:329-36 pubmed
    ..High-pressure fluorescence in the vicinity of the liquid-solid phase transition of the 2-NP/DEA and 2-NP/monoethylamine mixtures, is highlighted and discussed. ..
  12. Hanawa F, Tahara S, Towers G. Antifungal nitro compounds from skunk cabbage (Lysichitum americanum) leaves treated with cupric chloride. Phytochemistry. 2000;53:55-8 pubmed
    ..Both compounds were isolated for the first time from this species and the former was isolated from natural sources for the first time. This is the first report on stress metabolites from a member of the Araceae. ..
  13. Heroux A, Bozinovski D, Valley M, Fitzpatrick P, Orville A. Crystal structures of intermediates in the nitroalkane oxidase reaction. Biochemistry. 2009;48:3407-16 pubmed publisher
    ..Consequently, these results provide important structural descriptions of several steps along the nitroalkane oxidase reaction cycle. ..
  14. Pahari P, Chaturvedi S. Determination of best-fit potential parameters for a reactive force field using a genetic algorithm. J Mol Model. 2012;18:1049-61 pubmed publisher
    ..As a test problem, the use of the algorithm has been demonstrated for nitromethane and its decomposition products. ..
  15. Schoeps K, Stone Elander S, Halldin C. On-line synthesis of [11C]nitroalkanes. Int J Rad Appl Instrum A. 1989;40:261-2 pubmed
    ..The total radiochemical yields, starting from [11C]carbon dioxide, were of the order of 25-55% with an overall synthesis time of 8-15 min. ..
  16. Reszka K, Bilski P, Chignell C, Dillon J. Free radical reactions photosensitized by the human lens component, kynurenine: an EPR and spin trapping investigation. Free Radic Biol Med. 1996;20:23-34 pubmed
    ..We postulate that: (i) 3HKG may be able to photoinitiate free radical reactions in vivo, and (ii) oxygen is an important factor determining the yields of free radical processes initiated by lenticular chromophores. ..
  17. Andrae U, Kreis P, Coughtrie M, Pabel U, Meinl W, Bartsch I, et al. Activation of propane 2-nitronate to a genotoxicant in V79-derived cell lines engineered for the expression of rat hepatic sulfotransferases. Mutat Res. 1999;439:191-7 pubmed
    ..The results corroborate the essential role of sulfotransferases in the metabolic activation of P2N to genotoxic products and identify two rat sulfotransferases which are capable of catalyzing the activation step. ..
  18. Sclar G. Encephalomyeloradiculoneuropathy following exposure to an industrial solvent. Clin Neurol Neurosurg. 1999;101:199-202 pubmed
    ..Similar findings have been reported following 1-bromopropane exposure in rats. I hypothesize that this patient's symptoms may have been due to 1-bromopropane-induced neurotoxicity. ..
  19. Freitas M, Rittner R. Is there a general rule for the gauche effect in the conformational isomerism of 1,2-disubstituted ethanes?. J Phys Chem A. 2007;111:7233-6 pubmed
  20. Zhang F, Cheng X, Liu Z, Lou Q, Zhou J, Wang Z. Calculations of bond dissociation energies and dipole moments in energetic materials using density-functional methods. J Hazard Mater. 2007;147:658-62 pubmed
    ..The Becke-3/Perdew 86 in conjunction with 6-31G** is found to give the best results, although for the dipole moments of RDX, there is a slightly difference that B3P86/6-31G** is less reliable than B3P86/6-31+G**. ..
  21. Vojtech M, Petrušová M, Valent I, Pribulová B, Petrus L. Preparation of D-galactofuranosyl nitromethanes: a revision and a new approach. Carbohydr Res. 2011;346:715-21 pubmed publisher
    ..The relevant kinetic parameters of the latter transformation are determined by a curve fitting using the nonlinear least-squares Marquardt-Levenberg algorithm. ..
  22. Goodpaster J, McGuffin V. Fluorescence quenching as an indirect detection method for nitrated explosives. Anal Chem. 2001;73:2004-11 pubmed
    ..The indirect fluorescence quenching method shows increased sensitivity and selectivity over traditional UV-visible absorbance as well as the ability to detect a wider range of organic and inorganic nitrated compounds. ..
  23. Yenjai P, Chaiear N, Charerntanyarak L, Boonmee M. Hazardous gases and oxygen depletion in a wet paddy pile: an experimental study in a simulating underground rice mill pit, Thailand. Ind Health. 2012;50:540-7 pubmed
    ..7% to 4.1%). This study suggested that hazardous gases could be emitted in moist paddy piles, and their concentrations could increase with increasing moisture content and piling time period. ..
  24. Alizadeh N. A comparison of complexation of Li+ ion with macrocyclic ligands 15-crown-5 and 12-crown-4 in binary nitromethane-acetonitrile mixtures by using lithium-7 NMR technique and ab initio calculation. Spectrochim Acta A Mol Biomol Spectrosc. 2011;78:488-93 pubmed publisher
    ..The optimized structures of the free ligands and their 1:1 and 2:1 complexes with Li+ ion were predicted by ab initio theoretical calculations using the Gaussian 98 software, and the results are discussed. ..
  25. Ibrahim M, Prigol M, Hassan W, Nogueira C, Rocha J. Protective effect of binaphthyl diselenide, a synthetic organoselenium compound, on 2-nitropropane-induced hepatotoxicity in rats. Cell Biochem Funct. 2010;28:258-65 pubmed publisher
    ..Results presented here indicate that the protective mechanism of (NapSe)(2) against 2-NP hepatotoxicity is possibly linked to its antioxidant activity. ..
  26. Robak M, Trincado M, Ellman J. Enantioselective aza-Henry reaction with an N-sulfinyl urea organocatalyst. J Am Chem Soc. 2007;129:15110-1 pubmed
  27. Ilieva E, Petkova N, Nikolova R. A new and efficient method for the synthesis of 3,4-disubstituted pyrrolidine-2,5-diones. Molecules. 2012;17:4936-49 pubmed publisher
    ..The reaction involved a simple and convenient experimental procedure. The applicability of the rearrangement reaction is determined. ..
  28. Kim S, Hayashi K, Kitano Y, Tada M, Chiba K. Anodic modification of proline derivatives using a lithium perchlorate/nitromethane electrolyte solution. Org Lett. 2002;4:3735-7 pubmed
    ..The iminium cation intermediates gave modified prolines by a reaction with nucleophiles under mild conditions. ..
  29. Kundu B, Richardson S, Swartz P, Matthews P, Richard A, DeMarini D. Mutagenicity in Salmonella of halonitromethanes: a recently recognized class of disinfection by-products in drinking water. Mutat Res. 2004;562:39-65 pubmed
    ..Because the HNMs are mutagenic in Salmonella (present study) and potent clastogens in mammalian cells [Environ. Sci. Technol. 38 (2004) 62], their presence in drinking water warrants further research on their potential health effects. ..
  30. Blay G, Hernández Olmos V, Pedro J. Enantioselective addition of nitromethane to alpha-keto esters catalyzed by copper(II)-iminopyridine complexes. Org Biomol Chem. 2008;6:468-76 pubmed publisher
    ..Good yields and modest to good enantioselectivities are obtained for a wide range of alpha-keto esters, bearing aromatic, alkyl or alkenyl groups attached to the ketone carbonyl group. ..
  31. Balazy M, Iesaki T, Park J, Jiang H, Kaminski P, Wolin M. Vicinal nitrohydroxyeicosatrienoic acids: vasodilator lipids formed by reaction of nitrogen dioxide with arachidonic acid. J Pharmacol Exp Ther. 2001;299:611-9 pubmed
    ..Thus, the oxidation product of NO, NO2, reacts with arachidonic acid to generate biologically active vicinal nitrohydroxyeicosatrienoic acids, which may be important endogenous mediators of vascular relaxation and sGC activation. ..
  32. Kato K, Zhang M, Suzuki K. Synthesis of (R,S)-[4-11C]baclofen via Michael addition of nitromethane labeled with short-lived 11C. Bioorg Med Chem Lett. 2009;19:6222-4 pubmed publisher
    ..4+/-1.8% radiochemical conversion in three steps within 20 min. ..
  33. Major D, Heroux A, Orville A, Valley M, Fitzpatrick P, Gao J. Differential quantum tunneling contributions in nitroalkane oxidase catalyzed and the uncatalyzed proton transfer reaction. Proc Natl Acad Sci U S A. 2009;106:20734-9 pubmed publisher
  34. Janzen I, Dossetor J, Seem C. Model car fuel poisoning. Ann Clin Biochem. 2005;42:308-9 pubmed
  35. Cabelof D, Raffoul J, Ge Y, Van Remmen H, Matherly L, Heydari A. Age-related loss of the DNA repair response following exposure to oxidative stress. J Gerontol A Biol Sci Med Sci. 2006;61:427-34 pubmed
    ..Our results are consistent with a reduced ability to process DNA damage with age. ..
  36. Gao J, Wong K, Major D. Combined QM/MM and path integral simulations of kinetic isotope effects in the proton transfer reaction between nitroethane and acetate ion in water. J Comput Chem. 2008;29:514-22 pubmed
  37. Chen J, Fu L, Zou Y, Chang N, Rong J, Xiao W. Pyrrolidinyl-sulfamide derivatives as a new class of bifunctional organocatalysts for direct asymmetric Michael addition of cyclohexanone to nitroalkenes. Org Biomol Chem. 2011;9:5280-7 pubmed publisher
    ..The desired Michael adducts were obtained in high chemical yields and excellent stereoselectivities (up to 99/1 dr and 95% ee). ..
  38. Francis K, Gadda G. Inflated kinetic isotope effects in the branched mechanism of Neurospora crassa 2-nitropropane dioxygenase. Biochemistry. 2009;48:2403-10 pubmed publisher
    ..The isotope effect on branching results in an inflation of the kinetic isotope observed for the nonoxidative pathway to values that are larger than the intrinsic values associated with CH bond cleavage...
  39. Wang J, Li X, Xie H, Liu B, Lin X. Hydrolase-catalyzed fast Henry reaction of nitroalkanes and aldehydes in organic media. J Biotechnol. 2010;145:240-3 pubmed publisher
    ..Seventeen products were obtained in short time with moderate to high yields. It is the first report on hydrolase-catalyzed fast Henry reaction in organic solvent. ..
  40. Wang L, Zhang X, Xiong H, Wang S. A novel nitromethane biosensor based on biocompatible conductive redox graphene-chitosan/hemoglobin/graphene/room temperature ionic liquid matrix. Biosens Bioelectron. 2010;26:991-5 pubmed publisher
    ..Besides this, the proposed biosensor exhibited fast amperometric response (<5s), low detection limit (6.0 × 10(-10)M), and excellent long-time storage stability for the determination of CH(3)NO(2). ..
  41. Valley M, Fenny N, Ali S, Fitzpatrick P. Characterization of active site residues of nitroalkane oxidase. Bioorg Chem. 2010;38:115-9 pubmed publisher
    ..Only the S171V and S171T mutations alter the rate constant for flavin oxidation. These results establish that these residues are not involved in catalysis, but rather are required for maintaining the protein structure. ..
  42. Izake E, Cletus B, Olds W, Sundarajoo S, Fredericks P, Jaatinen E. Deep Raman spectroscopy for the non-invasive standoff detection of concealed chemical threat agents. Talanta. 2012;94:342-7 pubmed publisher
    ..A new combined time and space resolved Raman spectrometer has been designed with nanosecond laser excitation and gated detection, making it of lower cost and complexity than picosecond-based laboratory systems. ..
  43. Li S, Huang K, Cao B, Zhang J, Wu W, Zhang X. Highly enantioselective hydrogenation of ?,?-disubstituted nitroalkenes. Angew Chem Int Ed Engl. 2012;51:8573-6 pubmed publisher
    ..This method results in enantiomerically pure nitroalkanes 2, which are versatile precursors for chemical synthesis. ..
  44. Walvoord R, Kozlowski M. Minimizing the amount of nitromethane in palladium-catalyzed cross-coupling with aryl halides. J Org Chem. 2013;78:8859-64 pubmed publisher
    ..The present transformation provides high yields at relatively low temperatures and tolerates an array of functionality, including heterocycles and substantial steric encumbrance. ..
  45. Hussain N, Conaway C, Guo N, Asaad W, Fiala E. Oxidative DNA and RNA damage in rat liver due to acetoxime: similarity to effects of 2-nitropropane. Carcinogenesis. 1990;11:1013-6 pubmed
    ..In addition, the data support the hypothesis that the hepatocarcinogenicity of ACO depends on its partial in vivo N-oxidation to 2-NP. ..
  46. Anderson R, Jung Y, Genovese K, McReynolds J, Callaway T, Edrington T, et al. Low level nitrate or nitroethane preconditioning enhances the bactericidal effect of suboptimal experimental chlorate treatment against Escherichia coli and Salmonella Typhimurium but not Campylobacter in swine. Foodborne Pathog Dis. 2006;3:461-5 pubmed
  47. Petrušová M, Vojtech M, Pribulová B, Lattova E, Matulova M, Poláková M, et al. Extension of the Nef reaction to C-glycosylnitromethanes. Carbohydr Res. 2006;341:2019-25 pubmed
  48. Cook M, Clark R. Creatinine elevation associated with nitromethane exposure: a marker of potential methanol toxicity. J Emerg Med. 2007;33:249-53 pubmed
    ..Also, the degree to which the serum creatinine is elevated may indicate the severity of methanol poisoning. ..
  49. Riis B, Risom L, Loft S, Poulsen H. OGG1 mRNA expression and incision activity in rats are higher in foetal tissue than in adult liver tissue while 8-oxo-2'-deoxyguanosine levels are unchanged. DNA Repair (Amst). 2002;1:709-17 pubmed
    ..In conclusion, this study confirms that foetal tissue has increased levels of OGG1 mRNA and correspondingly an enhanced incision activity on an 8-oxodG substrate in a crude tissue extract. ..
  50. Trost B, Yeh V. A dinuclear Zn catalyst for the asymmetric nitroaldol (Henry) reaction. Angew Chem Int Ed Engl. 2002;41:861-3 pubmed
  51. Liu F, Wang Z, Song X, Zhang S, Liu H. The Henry reaction of (1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-1,4:3,6-dianhydro-D-fructose 5,5'-dinitrate. Different reactive features of nitromethane to nitroethane. Carbohydr Res. 2009;344:2439-43 pubmed publisher
    ..But when using nitroethane the reaction gave a (2S)-beta-nitroalcohol with an inverted configuration at vicinal carbon C-1. Two stereogenic centers were generated, and one was altered in the reaction. ..
  52. Liao J, Sun J, Yu B. An improved procedure for nucleoside synthesis using glycosyl trifluoroacetimidates as donors. Carbohydr Res. 2009;344:1034-8 pubmed publisher
    ..structure: see text]. ..
  53. Appalakondaiah S, Vaitheeswaran G, Lebegue S. A DFT study on structural, vibrational properties, and quasiparticle band structure of solid nitromethane. J Chem Phys. 2013;138:184705 pubmed publisher
    ..The static dielectric constant and refractive indices along the three inequivalent crystallographic directions indicate that this material has a considerable optical anisotropy. ..