Disease relevance of nitromethane

• False elevation of serum creatinine following skin absorption of nitromethane complicates the clinical diagnosis of rhabdomyolysis [1].
• Potential excited states are identified for the magnetron (MGN) values for quinones, thermal charge transfer (TCT) values for CS2, C6F6, SF6 and photoelectron spectroscopy (PES) values for O2, NO, nitromethane, and the nucleic acids [2].
• Peripheral neuropathy in workers exposed to nitromethane [3].
• Under certain industrial conditions the conversion of nitromethane to methylisocyanide may result in toxicity particularly in the basal ganglia and cerebellum following chronic low level exposure [4].
• Occupational allergic contact dermatitis to nitromethane [5].

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

• Subchronic inhalation toxicity of nitromethane and 2-nitropropane [11].

Biological context of nitromethane

• Using S-2,3-O-isopropylideneglyceraldehyde (4) as the source of chirality, both routes are based on a diastereoselective Michael addition of nitromethane to give predominantly the syn congeners 6 followed by a Nef oxidation and cyclization to afford lactone acetals 8, which are reduced and cyclized to give 2 [12].
• A nitromethane-mediated Fridel-Crafts acylation of 7 with chloromethylnicotinate 9 was developed to prepare ketone 10 in 68% yield [13].
• Nitromethane, which caused mammary gland tumors by inhalation exposure in female rats, harderian gland and lung tumors in male and female mice, and liver tumors in female mice by inhalation, failed to increase tumors in either guppies or medaka [14].
• While it cannot be definitively concluded that these two workers developed peripheral neuropathy secondary to exposures at work, occupational exposure to nitromethane appears to be the most likely etiology [3].
• The ready formation of a nitromethane inclusion complex in aqueous nitromethane, and the subtleties of its molecular structure amply demonstrate the ease with which water is expelled from the alpha-CD cavity by a more hydrophobic co-solvent [15].

Anatomical context of nitromethane

• The hepatic effects of nitromethane were restricted to decreased cytochrome c reductase activity with proliferation of smooth endoplasmic reticulum [16].
• N-alkylation with hexyl bromide and nitromethane gave rise to the quanternized PVDF-g-PBIEA-ar-QPDMAEMA membranes with polycation chains chemically tethered on the membrane surface, including the pore surfaces [17].

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

• Nitromethane as solvent in capillary electrophoresis [26].
• PC was found to be superior to nitromethane, the only reported PAH selective quencher used in HPLC [27].
• When nitromethane is doped with water, the water forms hydrogen bonds to the solute, interfering with the formation of the doubly hydrogen-bonded dimers, which is consistent with the crystallization of form I from this hygroscopic solvent when it is not dried [28].
• In this approach, the petroleum sample is extracted with nitromethane and then separated by capillary liquid chromatography with laser-induced fluorescence detection [29].

References