2.0 2012-08-09 09:16:16 -0600 2015-09-13 12:56:16 -0600 ECMDB21444 M2MDB001839 Hydroxylamine Hydroxylamine is a reactive chemical with formula NH2OH. It can be considered a hybrid of ammonia and water due to parallels it shares with each. At room temperature pure NH2OH is ordinarily a white, unstable crystalline, hygroscopic compound; however it is almost always encountered as an aqueous solution. It is a colorless inorganic compound used in organic synthesis and as a reducing agent, due to its ability to donate nitric oxide. Hydroxylamine may explode on heating. It is an irritant to the respiratory tract, skin, eyes, and other mucous membranes. It may be absorbed through the skin, is harmful if swallowed, and is a possible mutagen. NH2OH is an intermediate in the biological nitrification. The oxidation of NH3 is mediated by HAO (hydroxylamine oxidoreductase). (1) hydroxylamine Amino alcohol Amino-alcohol Dihydridohydroxidonitrogen Hydroxyamine hydrochloride Hydroxyl amine Hydroxylamine chloride Hydroxylamine hydrochloride Hydroxylamine-1-hydrochloride Hydroxylammonium chloride Nitroxide Oxammonium Oxammonium hydrochloride Oxyammonia H3NO 33.0299 33.021463723 hydroxylamine hydroxylamine 7803-49-8 NO InChI=1S/H3NO/c1-2/h2H,1H2 AVXURJPOCDRRFD-UHFFFAOYSA-N Solid Cytoplasm melting_point 33 oC logp -0.74 ChemAxon pka_strongest_acidic 17.65 ChemAxon pka_strongest_basic 3.94 ChemAxon iupac hydroxylamine ChemAxon average_mass 33.0299 ChemAxon mono_mass 33.021463723 ChemAxon smiles NO ChemAxon formula H3NO ChemAxon inchi InChI=1S/H3NO/c1-2/h2H,1H2 ChemAxon inchikey AVXURJPOCDRRFD-UHFFFAOYSA-N ChemAxon polar_surface_area 46.25 ChemAxon refractivity 7.85 ChemAxon polarizability 2.78 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Nitrogen metabolism The biological process of the nitrogen cycle is a complex interplay among many microorganisms catalyzing different reactions, where nitrogen is found in various oxidation states ranging from +5 in nitrate to -3 in ammonia. The ability of fixing atmospheric nitrogen by the nitrogenase enzyme complex is present in restricted prokaryotes (diazotrophs). The other reduction pathways are assimilatory nitrate reduction and dissimilatory nitrate reduction both for conversion to ammonia, and denitrification. Denitrification is a respiration in which nitrate or nitrite is reduced as a terminal electron acceptor under low oxygen or anoxic conditions, producing gaseous nitrogen compounds (N2, NO and N2O) to the atmosphere. Nitrate can be introduced into the cytoplasm through a nitrate:nitrite antiporter NarK or a nitrate / nitrite transporter NarU. Nitrate is then reduced by a Nitrate Reductase resulting in the release of water, an acceptor and a Nitrite. Nitrite can also be introduced into the cytoplasm through a nitrate:nitrite antiporter NarK Nitrite can be reduced a NADPH dependent nitrite reductase resulting in water and NAD and Ammonia. Nitrite can interact with hydrogen ion, ferrocytochrome c through a cytochrome c-552 ferricytochrome resulting in the release of ferricytochrome c, water and ammonia Another process by which ammonia is produced is by a reversible reaction of hydroxylamine with a reduced acceptor through a hydroxylamine reductase resulting in an acceptor, water and ammonia. Water and carbon dioxide react through a carbonate dehydratase resulting in carbamic acid. This compound reacts spontaneously with hydrogen ion resulting in the release of carbon dioxide and ammonia. Carbon dioxide can interact with water through a carbonic anhydrase resulting in hydrogen carbonate. This compound interacts with cyanate and hydrogen ion through a cyanate hydratase resulting in a carbamic acid. Ammonia can be metabolized by reacting with L-glutamine and ATP driven glutamine synthetase resulting in ADP, phosphate and L-glutamine. The latter compound reacts with oxoglutaric acid and hydrogen ion through a NADPH dependent glutamate synthase resulting in the release of NADP and L-glutamic acid. L-glutamic acid reacts with water through a NADP-specific glutamate dehydrogenase resulting in the release of oxoglutaric acid, NADPH, hydrogen ion and ammonia. PW000755 ec00910 Metabolic Specdb::CMs 838 Specdb::CMs 915 Specdb::CMs 13988 Specdb::CMs 30875 Specdb::CMs 31451 Specdb::CMs 32357 Specdb::CMs 132590 Specdb::CMs 140324 Specdb::MsMs 2251 Specdb::MsMs 2252 Specdb::MsMs 2253 Specdb::MsMs 296869 Specdb::MsMs 296870 Specdb::MsMs 296871 Specdb::MsMs 338248 Specdb::MsMs 338249 Specdb::MsMs 338250 Specdb::MsMs 2355039 Specdb::MsMs 2355040 Specdb::MsMs 2355041 Specdb::MsMs 2607990 Specdb::MsMs 2607991 Specdb::MsMs 2607992 HMDB03338 787 766 C00192 15429 HOA Hydroxylamine van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). 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Epub 2006 Feb 28. 16507648 Winter HR, Unadkat JD: Identification of cytochrome P450 and arylamine N-acetyltransferase isoforms involved in sulfadiazine metabolism. Drug Metab Dispos. 2005 Jul;33(7):969-76. Epub 2005 Apr 20. 15843491 Coleman MD: Dapsone: modes of action, toxicity and possible strategies for increasing patient tolerance. Br J Dermatol. 1993 Nov;129(5):507-13. 8251346 http://hmdb.ca/system/metabolites/msds/000/002/919/original/HMDB03338.pdf?1358463311 Hydroxylamine reductase P75825 HCP_ECOLI hcp http://ecmdb.ca/proteins/P75825.xml Ammonia + Water + Acceptor <> Hydroxylamine + Reduced acceptor R00284 Hydroxylamine + cytochrome c nitrite reductase <> Ammonia + Water + cytochrome c nitrite reductase PW_R002429