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Record Information
Version2.0
Creation Date2009-03-06 18:58:17 UTC
Update Date2014-12-24 20:21:20 UTC
Accession NumberT3D0212
Identification
Common NameNitrite
ClassSmall Molecule
DescriptionNitrite is a nitrite compound is either a salt or an ester of nitrous acid. Sodium nitrite is used for the curing of meat because it prevents bacterial growth and, in a reaction with the meat's myoglobin, gives the product a desirable dark red color. Nitrite can be reduced to nitric oxide or ammonia by many species of bacteria. Under hypoxic conditions, nitrite may release nitric oxide, which causes potent vasodilation. Several mechanisms for nitrite conversion to NO have been described including enzymatic reduction by xanthine oxidoreductase, the mitochondria, and NO synthase (NOS), as well as nonenzymatic acidic disproportionation. -- Wikipedia.
Compound Type
  • Food Toxin
  • Inorganic Compound
  • Metabolite
  • Natural Compound
  • Nitrite
  • Non-Metal
  • Pesticide
Chemical Structure
Thumb
Synonyms
Synonym
Nitrite anion
Nitrite ion
Nitrogen dioxide
Nitrogen dioxide ion
Nitrogen peroxide ion
Chemical FormulaNO2
Average Molecular Mass46.006 g/mol
Monoisotopic Mass45.993 g/mol
CAS Registry Number14797-65-0
IUPAC Namenitrous acid
Traditional Namenitrous acid
SMILES[O-]N=O
InChI IdentifierInChI=1S/HNO2/c2-1-3/h(H,2,3)/p-1
InChI KeyInChIKey=IOVCWXUNBOPUCH-UHFFFAOYSA-M
Chemical Taxonomy
Description belongs to the class of inorganic compounds known as non-metal nitrites. These are inorganic non-metallic compounds containing a nitrite as its largest oxoanion.
KingdomInorganic compounds
Super ClassHomogeneous non-metal compounds
ClassNon-metal oxoanionic compounds
Sub ClassNon-metal nitrites
Direct ParentNon-metal nitrites
Alternative Parents
Substituents
  • Non-metal nitrite
  • Inorganic nitrite
  • Inorganic oxide
Molecular FrameworkNot Available
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Bladder
  • Brain
  • Erythrocyte
  • Fibroblasts
  • Heart
  • Intestine
  • Kidney
  • Leukocyte
  • Liver
  • Lung
  • Neutrophil
  • Oesophagus
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Spleen
  • Testes
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
logP0.17ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.66 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity8.72 m³·mol⁻¹ChemAxon
Polarizability2.81 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0007-9000000000-9cf82c70d7bc0883ea95JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0005-9000000000-e52588fd7e5b6989584dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0007-9000000000-891acfcb7562d9875939JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-701578487c4dc8b94d22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-701578487c4dc8b94d22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-701578487c4dc8b94d22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-9c61b79c18a51c772d86JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-9c61b79c18a51c772d86JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-9c61b79c18a51c772d86JSpectraViewer
Toxicity Profile
Route of ExposureOral (6) ; inhalation (6)
Mechanism of ToxicityNitrite causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen. (1, 7)
MetabolismIntake of some amount of nitrates and nitrites is a normal part of the nitrogen cycle in humans. In vivo conversion of nitrates to nitrites can occur in the gastrointestional tract under the right conditions, significantly enhancing nitrates' toxic potency. The major metabolic pathway for nitrate is conversion to nitrite, and then to ammonia. Nitrites, nitrates, and their metabolites are excreted in the urine. (6)
Toxicity ValuesNot Available
Lethal Dose10 to 100 mg/kg for an adult human. (8)
Carcinogenicity (IARC Classification)Ingested nitrate or nitrite under conditions that result in endogenous nitrosation is probably carcinogenic to humans (Group 2A). (5)
Uses/SourcesNitrates and nitrites are naturally produced and may also be found in pesticides. Exposure usually occurs from contact with contaminated soil, food water. Nitrates may also be found in certain drugs. (6)
Minimum Risk LevelNot Available
Health EffectsNitrite poisoning causes methemoglobinemia. Nitrites may cause pregnancy complications and developmental effects. They may also be carcinogenic. (6)
SymptomsNitrite poisoning causes methemoglobinemia. Symptoms include cyanosis, cardiac dysrhythmias and circulatory failure, and progressive central nervous system (CNS) effects. CNS effects can range from mild dizziness and lethargy to coma and convulsions. (6)
TreatmentMethemoglobinemia can be treated with supplemental oxygen and methylene blue 1% solution administered intravenously slowly over five minutes followed by IV flush with normal saline. Methylene blue restores the iron in hemoglobin to its normal (reduced) oxygen-carrying state. (7)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB02786
PubChem Compound ID946
ChEMBL IDNot Available
ChemSpider ID921
KEGG IDC00088
UniProt IDNot Available
OMIM ID
ChEBI ID16301
BioCyc IDNITRITE
CTD IDNot Available
Stitch IDNitrite
PDB IDNO2
ACToR ID6495
Wikipedia LinkNitrite
References
Synthesis ReferenceNakata, Sumio; Eiki, Toshio; Tanaka, Norihiro; Koyama, Tadashi; Tsukui, Hiroto; Watanabe, Shizuo. Production of nitrite ions from trinitrophenyl myosin and from trinitrophenyl subfragment-1. Journal of Biochemistry (Tokyo, Japan) (1986), 99(1), 27-32.
MSDSLink
General References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Takahama U, Oniki T, Murata H: The presence of 4-hydroxyphenylacetic acid in human saliva and the possibility of its nitration by salivary nitrite in the stomach. FEBS Lett. 2002 May 8;518(1-3):116-8. [11997029 ]
  3. Miyado T, Tanaka Y, Nagai H, Takeda S, Saito K, Fukushi K, Yoshida Y, Wakida S, Niki E: Simultaneous determination of nitrate and nitrite in biological fluids by capillary electrophoresis and preliminary study on their determination by microchip capillary electrophoresis. J Chromatogr A. 2004 Oct 8;1051(1-2):185-91. [15532572 ]
  4. Tsikas D: Methods of quantitative analysis of the nitric oxide metabolites nitrite and nitrate in human biological fluids. Free Radic Res. 2005 Aug;39(8):797-815. [16036360 ]
  5. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  6. ATSDR - Agency for Toxic Substances and Disease Registry (2007). Case Studies in Environmental Medicine. Nitrate/Nitrite Toxicity. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  7. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
  8. International Programme on Chemical Safety (IPCS) INCHEM (1996). Poison Information Monograph for Nitrates and Nitrites. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBA1
Uniprot ID:
P69905
Molecular Weight:
15257.405 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
Gene Name:
HBB
Uniprot ID:
P68871
Molecular Weight:
15998.34 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBD
Uniprot ID:
P02042
Molecular Weight:
16055.41 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
The epsilon chain is a beta-type chain of early mammalian embryonic hemoglobin.
Gene Name:
HBE1
Uniprot ID:
P02100
Molecular Weight:
16202.71 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Gene Name:
HBG1
Uniprot ID:
P69891
Molecular Weight:
16140.37 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Specific Function:
Heme binding
Gene Name:
HBG2
Uniprot ID:
P69892
Molecular Weight:
16126.35 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBM
Uniprot ID:
Q6B0K9
Molecular Weight:
15617.97 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBQ1
Uniprot ID:
P09105
Molecular Weight:
15507.575 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
General Function:
Oxygen transporter activity
Specific Function:
The zeta chain is an alpha-type chain of mammalian embryonic hemoglobin.
Gene Name:
HBZ
Uniprot ID:
P02008
Molecular Weight:
15636.845 Da
References
  1. Keszler A, Piknova B, Schechter AN, Hogg N: The reaction between nitrite and oxyhemoglobin: a mechanistic study. J Biol Chem. 2008 Apr 11;283(15):9615-22. doi: 10.1074/jbc.M705630200. Epub 2008 Jan 17. [18203719 ]
  2. Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]