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Record Information
Version	2.0
Creation Date	2012-08-09 09:16:16 -0600
Update Date	2015-09-13 12:56:16 -0600
Secondary Accession Numbers	ECMDB21444
Identification
Name:	Hydroxylamine
Description	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).
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0x9143bd7c> Close
Synonyms:	(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
Chemical Formula:	H3NO
Weight:	Average: 33.0299 Monoisotopic: 33.021463723
InChI Key:	AVXURJPOCDRRFD-UHFFFAOYSA-N
InChI:	InChI=1S/H3NO/c1-2/h2H,1H2
CAS number:	7803-49-8
IUPAC Name:	hydroxylamine
Traditional IUPAC Name:	hydroxylamine
SMILES:	NO
Chemical Taxonomy
Description	belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'.
Kingdom	Inorganic compounds
Super Class	Homogeneous non-metal compounds
Class	Homogeneous other non-metal compounds
Sub Class	Not Available
Direct Parent	Homogeneous other non-metal compounds
Alternative Parents	Not Available
Substituents	Homogeneous other non metal
Molecular Framework	Not Available
External Descriptors	hydroxylamines (CHEBI:15429 ) a small molecule (HYDROXYLAMINE )
Physical Properties
State:	Solid
Charge:	0
Melting point:	33 °C
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source logP -0.74 ChemAxon pKa (Strongest Acidic) 17.65 ChemAxon pKa (Strongest Basic) 3.94 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 46.25 Ų ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 7.85 m³·mol⁻¹ ChemAxon Polarizability 2.78 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Ammonia + Water + Acceptor <> Hydroxylamine + Reduced acceptor Hydroxylamine + cytochrome c nitrite reductase <> Ammonia + Water + cytochrome c nitrite reductase
SMPDB Pathways:	Nitrogen metabolism PW000755
KEGG Pathways:	Nitrogen metabolism ec00910
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) splash10-00di-9800000000-40500c2ce42330f68e23 View in MoNA GC-MS GC-MS Spectrum - GC-MS (3 TMS) splash10-001j-1900000000-380d2510f339c8852cae View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00di-9800000000-40500c2ce42330f68e23 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-001j-1900000000-380d2510f339c8852cae View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00m1-1900000000-7c1a1a9c2955e5f4d75e View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-001i-9000000000-6a1320306a7bbc43c258 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-001i-9000000000-17862dd274dc5ae95e9b View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-001i-9000000000-c7d671f97d82bbe3e458 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-001i-9000000000-36b50bedfc3b86b95fdf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-001i-9000000000-190eddac91b76eed9065 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-001i-9000000000-190eddac91b76eed9065 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-001i-9000000000-190eddac91b76eed9065 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001i-9000000000-20928e005423160892f3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-9000000000-20928e005423160892f3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-001i-9000000000-20928e005423160892f3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-001i-9000000000-190eddac91b76eed9065 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-001i-9000000000-190eddac91b76eed9065 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-001i-9000000000-190eddac91b76eed9065 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001i-9000000000-6c136ec6f9ff4bb55445 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-9000000000-6c136ec6f9ff4bb55445 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-001i-9000000000-6c136ec6f9ff4bb55445 View in MoNA
References
References:	Alonso A, Meirelles NC, Tabak M: Stratum corneum intercellular lipid as compared to erythrocyte ghosts: an ESR study of thermotropic behavior and nitroxide reduction. Electron Spin Resonance. Physiol Chem Phys Med NMR. 1995;27(1):63-72. Pubmed: 7617746 Atamna H, Robinson C, Ingersoll R, Elliott H, Ames BN: N-t-Butyl hydroxylamine is an antioxidant that reverses age-related changes in mitochondria in vivo and in vitro. FASEB J. 2001 Oct;15(12):2196-204. Pubmed: 11641246 Coleman MD, Jacobus DP: Reduction of dapsone hydroxylamine to dapsone during methaemoglobin formation in human erythrocytes in vitro--II. Movement of dapsone across a semipermeable membrane into erythrocytes and plasma. Biochem Pharmacol. 1993 Oct 19;46(8):1363-8. Pubmed: 8240384 Coleman MD: Dapsone: modes of action, toxicity and possible strategies for increasing patient tolerance. Br J Dermatol. 1993 Nov;129(5):507-13. Pubmed: 8251346 Cribb AE, Spielberg SP: Sulfamethoxazole is metabolized to the hydroxylamine in humans. Clin Pharmacol Ther. 1992 May;51(5):522-6. Pubmed: 1587066 Forsyth NR, Evans AP, Shay JW, Wright WE: Developmental differences in the immortalization of lung fibroblasts by telomerase. Aging Cell. 2003 Oct;2(5):235-43. Pubmed: 14570231 Fuchs J, Freisleben HJ, Podda M, Zimmer G, Milbradt R, Packer L: Nitroxide radical biostability in skin. Free Radic Biol Med. 1993 Oct;15(4):415-23. Pubmed: 8225023 Goda R, Nagai D, Akiyama Y, Nishikawa K, Ikemoto I, Aizawa Y, Nagata K, Yamazoe Y: Detection of a new N-oxidized metabolite of flutamide, N-[4-nitro-3-(trifluoromethyl)phenyl]hydroxylamine, in human liver microsomes and urine of prostate cancer patients. Drug Metab Dispos. 2006 May;34(5):828-35. Epub 2006 Feb 28. Pubmed: 16507648 Kurian JR, Bajad SU, Miller JL, Chin NA, Trepanier LA: NADH cytochrome b5 reductase and cytochrome b5 catalyze the microsomal reduction of xenobiotic hydroxylamines and amidoximes in humans. J Pharmacol Exp Ther. 2004 Dec;311(3):1171-8. Epub 2004 Aug 9. Pubmed: 15302896 Lin J, Cashman JR: Detoxication of tyramine by the flavin-containing monooxygenase: stereoselective formation of the trans oxime. Chem Res Toxicol. 1997 Aug;10(8):842-52. Pubmed: 9282832 Peng SX, Strojnowski MJ, Hu JK, Smith BJ, Eichhold TH, Wehmeyer KR, Pikul S, Almstead NG: Gas chromatographic-mass spectrometric analysis of hydroxylamine for monitoring the metabolic hydrolysis of metalloprotease inhibitors in rat and human liver microsomes. J Chromatogr B Biomed Sci Appl. 1999 Mar 5;724(1):181-7. Pubmed: 10202971 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 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. Pubmed: 15843491 Yang X, Arosio P, Chasteen ND: Molecular diffusion into ferritin: pathways, temperature dependence, incubation time, and concentration effects. Biophys J. 2000 Apr;78(4):2049-59. Pubmed: 10733983
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 15429 HMDB ID HMDB03338 Pubchem Compound ID 787 Kegg ID C00192 ChemSpider ID 766 Wikipedia Hydroxylamine BioCyc ID Not Available Ligand Expo HOA

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