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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-08-12 19:06:36 UTC

Update Date

2023-02-21 17:16:36 UTC

HMDB ID

HMDB0003338

Secondary Accession Numbers

HMDB0060880
HMDB03338
HMDB60880

Metabolite Identification

Common 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. A colorless inorganic compound (HONH2) 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
[NH2OH]	ChEBI
H2NHO	ChEBI
HYDROXYAMINE	ChEBI
Hydroxylamin	ChEBI
Oxyammonia	ChEBI
NH2OH	Kegg
Hydroxylamine hydrochloride	MeSH
Hydroxylammonium chloride	MeSH
(1) Hydroxylamine	HMDB
Dihydridohydroxidonitrogen	HMDB
Hydroxyamine hydrochloride	HMDB
Hydroxylamine chloride	HMDB
Hydroxylamine-1-hydrochloride	HMDB
Nitroxide	HMDB
Oxammonium	HMDB
Oxammonium hydrochloride	HMDB
Chloride, hydroxylammonium	MeSH, HMDB
Hydrochloride, hydroxylamine	MeSH, HMDB

Chemical Formula

H₃NO

Average Molecular Weight

33.0299

Monoisotopic Molecular Weight

33.021463723

IUPAC Name

hydroxylamine

Traditional Name

hydroxylamine

CAS Registry Number

7803-49-8

SMILES

InChI Identifier

InChI=1S/H3NO/c1-2/h2H,1H2

InChI Key

AVXURJPOCDRRFD-UHFFFAOYSA-N

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0003338)

Organ

Cell

Fibroblast

Fibroblast (HMDB: HMDB0003338)

Fibroblasts (HMDB: HMDB0003338)

Tissue

Epithelium

Epidermis (HMDB: HMDB0003338)

Excreta

Biofluid or Excreta

Urine (PMID: 21543078)

Cellular substructure

Cytoplasm (HMDB: HMDB0003338)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003338)

Source

Endogenous

Endogenous (HMDB: HMDB0003338)

Plant

Fabaceae (HMDB: HMDB0003338)

Exogenous

Food

Food (HMDB: HMDB0003338)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Pulse

Bean

Mung bean (FooDB: FOOD00200)
Gram bean (FooDB: FOOD00199)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Not Available

Signaling molecule (HMDB: HMDB0003338)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	33 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	7.85 m³·mol⁻¹	ChemAxon
Polarizability	2.78 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	111.698	30932474
DeepCCS	[M-H]-	109.903	30932474
DeepCCS	[M-2H]-	145.099	30932474
DeepCCS	[M+Na]+	118.564	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxylamine	NO	1330.5	Standard polar	33892256
Hydroxylamine	NO	569.5	Standard non polar	33892256
Hydroxylamine	NO	590.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxylamine,1TMS,isomer #1	C[Si](C)(C)NO	725.9	Semi standard non polar	33892256
Hydroxylamine,1TMS,isomer #1	C[Si](C)(C)NO	763.8	Standard non polar	33892256
Hydroxylamine,1TMS,isomer #1	C[Si](C)(C)NO	1108.8	Standard polar	33892256
Hydroxylamine,2TMS,isomer #1	C[Si](C)(C)N(O)[Si](C)(C)C	927.3	Semi standard non polar	33892256
Hydroxylamine,2TMS,isomer #1	C[Si](C)(C)N(O)[Si](C)(C)C	923.4	Standard non polar	33892256
Hydroxylamine,2TMS,isomer #1	C[Si](C)(C)N(O)[Si](C)(C)C	1089.0	Standard polar	33892256
Hydroxylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NO	963.0	Semi standard non polar	33892256
Hydroxylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NO	944.6	Standard non polar	33892256
Hydroxylamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NO	1213.6	Standard polar	33892256
Hydroxylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(O)[Si](C)(C)C(C)(C)C	1329.1	Semi standard non polar	33892256
Hydroxylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(O)[Si](C)(C)C(C)(C)C	1298.2	Standard non polar	33892256
Hydroxylamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(O)[Si](C)(C)C(C)(C)C	1307.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Hydroxylamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9800000000-40500c2ce42330f68e23	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hydroxylamine GC-MS (3 TMS)	splash10-001j-1900000000-380d2510f339c8852cae	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hydroxylamine GC-EI-TOF (Non-derivatized)	splash10-00di-9800000000-40500c2ce42330f68e23	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hydroxylamine GC-MS (Non-derivatized)	splash10-001j-1900000000-380d2510f339c8852cae	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Hydroxylamine GC-EI-TOF (Non-derivatized)	splash10-00m1-1900000000-7c1a1a9c2955e5f4d75e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-6a1320306a7bbc43c258	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxylamine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-001i-9000000000-17862dd274dc5ae95e9b	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxylamine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001i-9000000000-c7d671f97d82bbe3e458	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxylamine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-001i-9000000000-36b50bedfc3b86b95fdf	2012-07-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylamine 10V, Positive-QTOF	splash10-001i-9000000000-190eddac91b76eed9065	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylamine 20V, Positive-QTOF	splash10-001i-9000000000-190eddac91b76eed9065	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylamine 40V, Positive-QTOF	splash10-001i-9000000000-190eddac91b76eed9065	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylamine 10V, Negative-QTOF	splash10-001i-9000000000-20928e005423160892f3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylamine 20V, Negative-QTOF	splash10-001i-9000000000-20928e005423160892f3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylamine 40V, Negative-QTOF	splash10-001i-9000000000-20928e005423160892f3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylamine 10V, Positive-QTOF	splash10-001i-9000000000-190eddac91b76eed9065	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylamine 20V, Positive-QTOF	splash10-001i-9000000000-190eddac91b76eed9065	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylamine 40V, Positive-QTOF	splash10-001i-9000000000-190eddac91b76eed9065	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylamine 10V, Negative-QTOF	splash10-001i-9000000000-6c136ec6f9ff4bb55445	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylamine 20V, Negative-QTOF	splash10-001i-9000000000-6c136ec6f9ff4bb55445	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylamine 40V, Negative-QTOF	splash10-001i-9000000000-6c136ec6f9ff4bb55445	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Epidermis
Fibroblasts
Kidney
Liver
Spleen

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected but not Quantified	Not Quantified	Not Available	Not Available	Normal	21543078	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Hydroxylamine

METLIN ID

6894

PubChem Compound

787

PDB ID

Not Available

ChEBI ID

15429

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
Cribb AE, Spielberg SP: Sulfamethoxazole is metabolized to the hydroxylamine in humans. Clin Pharmacol Ther. 1992 May;51(5):522-6. [PubMed:1587066 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for Hydroxylamine (HMDB0003338)

MOL for HMDB0003338 (Hydroxylamine)

3D MOL for HMDB0003338 (Hydroxylamine)

3D SDF for HMDB0003338 (Hydroxylamine)

3D-SDF for HMDB0003338 (Hydroxylamine)

PDB for HMDB0003338 (Hydroxylamine)

3D PDB for HMDB0003338 (Hydroxylamine)

SMILES for HMDB0003338 (Hydroxylamine)

INCHI for HMDB0003338 (Hydroxylamine)

Structure for HMDB0003338 (Hydroxylamine)

3D Structure for HMDB0003338 (Hydroxylamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra