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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:42:21 UTC
Update Date2023-02-21 17:20:24 UTC
HMDB IDHMDB0031329
Secondary Accession Numbers
  • HMDB31329
Metabolite Identification
Common NameButyl nitrite
DescriptionButyl nitrite is found in animal foods. Butyl nitrite is a preservative for meats. Claimed not to generate nitrosamines as byproducts Amyl nitrite is employed medically to treat heart diseases such as angina and to treat cyanide poisoning. It is also used as an inhalant drug that induces a brief euphoria; whilst already intoxicated with stimulant drugs such as cocaine or ecstasy (see MDMA) the euphoric state intensifies and lasts for several minutes longer. Once some stimulative drugs wear off, a common side effect is a period of depression or anxiety, colloquially called a "come down"; amyl nitrite is sometimes used to "come up" again in order to stop the user from feeling lousy. Butyl nitrite is an alkyl nitrite made from butyl alcohol. It can be used as an antianginal. Butyl nitrite is also used recreationally as poppers
Structure
Data?1677000024
Synonyms
ValueSource
Butyl ester OF nitrous acidHMDB
N-Butyl nitriteHMDB, MeSH
N-C4H9ONOHMDB
NBNHMDB
Nitrous acid, butyl esterHMDB
Nitrous acid, N-butyl esterHMDB
N-Butyl nitrite, 15N-labeledMeSH, HMDB
Chemical FormulaC4H9NO2
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
IUPAC Namebutyl nitrite
Traditional Namebutyl nitrite
CAS Registry Number544-16-1
SMILES
CCCCON=O
InChI Identifier
InChI=1S/C4H9NO2/c1-2-3-4-7-5-6/h2-4H2,1H3
InChI KeyJQJPBYFTQAANLE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic o-nitroso compounds. These are organic compounds containing a n-nitroso group -ON=O.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassOrganic nitroso compounds
Direct ParentOrganic O-nitroso compounds
Alternative Parents
Substituents
  • Organic o-nitroso compound
  • Alkyl nitrite
  • Organic nitrite
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility12.8 g/LALOGPS
logP1.44ALOGPS
logP1.87ChemAxon
logS-0.91ALOGPS
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.66 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity27.08 m³·mol⁻¹ChemAxon
Polarizability10.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+120.62431661259
DarkChem[M-H]-115.57931661259
DeepCCS[M+H]+127.8130932474
DeepCCS[M-H]-125.91430932474
DeepCCS[M-2H]-161.39430932474
DeepCCS[M+Na]+135.81930932474
AllCCS[M+H]+123.232859911
AllCCS[M+H-H2O]+118.832859911
AllCCS[M+NH4]+127.232859911
AllCCS[M+Na]+128.432859911
AllCCS[M-H]-121.332859911
AllCCS[M+Na-2H]-125.132859911
AllCCS[M+HCOO]-129.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Butyl nitriteCCCCON=O799.5Standard polar33892256
Butyl nitriteCCCCON=O576.7Standard non polar33892256
Butyl nitriteCCCCON=O778.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Butyl nitrite GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vl-9000000000-60606d4dbf82f88007db2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butyl nitrite GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl nitrite 10V, Positive-QTOFsplash10-0zfr-8900000000-e1313c313380813bcc072016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl nitrite 20V, Positive-QTOFsplash10-0a4i-9100000000-7a38f300a34930eb87502016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl nitrite 40V, Positive-QTOFsplash10-0a4l-9000000000-7451dcfde52132f82a8d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl nitrite 10V, Negative-QTOFsplash10-0udi-2900000000-19eecc20b814f985eb682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl nitrite 20V, Negative-QTOFsplash10-0zfr-9500000000-db3a77751ebc808f34772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl nitrite 40V, Negative-QTOFsplash10-000g-9000000000-bc9b4764dc8a205255512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl nitrite 10V, Positive-QTOFsplash10-0a4i-9000000000-b4e932a5ebfdb66601cb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl nitrite 20V, Positive-QTOFsplash10-0a4i-9000000000-a80e9b0fd0ed5ca6c5282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl nitrite 40V, Positive-QTOFsplash10-0a4i-9000000000-db8392b5b998f0490a672021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl nitrite 10V, Negative-QTOFsplash10-0udi-2900000000-0e854c5eae20c8f3cffc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl nitrite 20V, Negative-QTOFsplash10-0002-9000000000-a0441e6336543cb884232021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butyl nitrite 40V, Negative-QTOFsplash10-0002-9000000000-210d2a10319099076cf32021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003391
KNApSAcK IDNot Available
Chemspider ID10530
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkButyl nitrite
METLIN IDNot Available
PubChem Compound10996
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .