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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:39 UTC
HMDB IDHMDB0001382
Secondary Accession Numbers
  • HMDB01382
Metabolite Identification
Common NameVaporole
DescriptionIsoamyl nitrite (IAN) has been used as antianginal agents for more than 100 years. It is now established that IAN cause direct vasorelaxation through vascular generation of NO and relaxation via a cyclic guanosine monophosphate-dependent process. (PMID: 8996213 ). IAN is a member of the family of volatile organic nitrites that exert vasodilatory effects and have recently exhibited a considerable potential for inhalation abuse. (PMID: 9829558 ). All nitrovasodilators act intracellularly by a common molecular mechanism. This is characterized by the release of nitric oxide (NO). This process basically depends on the presence of oxygen as electron acceptor from the sydnonimine molecule. Organic nitrites (such as IAN) require the interaction with a mercapto group to form a S-nitrosothiol intermediate, from which finally NO radicals are liberated. In the presence of thiol compounds organic nitrites (e.g., IAN) and nitrosothiols may act as intermediary products of NO generation. (PMID: 1683227 ).
Structure
Data?1676999739
Synonyms
ValueSource
3-Methylbutanol nitriteChEBI
3-Methylbutyl nitriteChEBI
AmilnitriteChEBI
Amyl nitrite IChEBI
Amyl nitrosumChEBI
IPNChEBI
Isopentyl nitriteChEBI
NitramylChEBI
Nitrous acid, 3-methylbutyl esterChEBI
Nitrous acid, isopentyl esterChEBI
Pentyl nitriteChEBI
Isoamyl nitriteKegg
AspiralKegg
Amyl nitritHMDB
Amyl nitrite (JP15/usp)HMDB
Amyl nitriteHMDB
Amyl nitrite(mixed isomers)HMDB
Isopentyl ester nitrous acidHMDB
Nitrite isopentyl alcoholHMDB
Nitrous acid 3-methylbutyl esterHMDB
Pentanoli nitrisHMDB
Vaporole amyl nitriteHMDB
VaporoleKEGG
Chemical FormulaC5H11NO2
Average Molecular Weight117.1463
Monoisotopic Molecular Weight117.078978601
IUPAC Name3-methylbutyl nitrite
Traditional Nameaspiral
CAS Registry Number110-46-3
SMILES
CC(C)CCON=O
InChI Identifier
InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3
InChI KeyOWFXIOWLTKNBAP-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 Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point99.2 °CNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.88 g/LALOGPS
logP1.87ALOGPS
logP2.16ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.66 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.63 m³·mol⁻¹ChemAxon
Polarizability12.63 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]+125.2531661259
DarkChem[M-H]-120.0531661259
AllCCS[M+H]+126.16832859911
AllCCS[M-H]-126.73332859911
DeepCCS[M+H]+129.96530932474
DeepCCS[M-H]-127.86630932474
DeepCCS[M-2H]-163.88430932474
DeepCCS[M+Na]+138.49130932474
AllCCS[M+H]+126.232859911
AllCCS[M+H-H2O]+122.032859911
AllCCS[M+NH4]+130.132859911
AllCCS[M+Na]+131.232859911
AllCCS[M-H]-126.732859911
AllCCS[M+Na-2H]-130.032859911
AllCCS[M+HCOO]-133.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VaporoleCC(C)CCON=O834.3Standard polar33892256
VaporoleCC(C)CCON=O678.4Standard non polar33892256
VaporoleCC(C)CCON=O843.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vaporole GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-7cd42a07f3940a578b462017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vaporole 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 - Vaporole 10V, Positive-QTOFsplash10-01b9-8900000000-9952ab742a1e8ce493232016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaporole 20V, Positive-QTOFsplash10-00xr-9100000000-87ae2e9bdf1f4804ab302016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaporole 40V, Positive-QTOFsplash10-0ab9-9000000000-9bb6338451463c8db89c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaporole 10V, Negative-QTOFsplash10-014i-2900000000-7c5ed4be18f51fc3c5152016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaporole 20V, Negative-QTOFsplash10-014i-9500000000-7d715aa0027b56813f452016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaporole 40V, Negative-QTOFsplash10-0a4j-9000000000-b6cdd36d8d07c56500742016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaporole 10V, Negative-QTOFsplash10-014r-7900000000-f488c41b56a34382a96b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaporole 20V, Negative-QTOFsplash10-0002-9000000000-a0441e6336543cb884232021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaporole 40V, Negative-QTOFsplash10-0002-9000000000-a0441e6336543cb884232021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaporole 10V, Positive-QTOFsplash10-01b9-9000000000-ec77cbf86b3d8ee8ad922021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaporole 20V, Positive-QTOFsplash10-05fr-9000000000-d2518b1e07a2fcd67eeb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vaporole 40V, Positive-QTOFsplash10-0006-9000000000-1f9d7edd509b1fd5b7c02021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart 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
  • Membrane (predicted from logP)
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 IDFDB022593
KNApSAcK IDNot Available
Chemspider ID7762
KEGG Compound IDC07457
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVaporole
METLIN IDNot Available
PubChem Compound8053
PDB IDNot Available
ChEBI ID2691
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceWilson, S. D.; Yang, E. F. Preparation of the pure isomers of amyl nitrite. Zhongguo Shenglixue Zazhi (1930), 4 391-2.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bauer JA, Nolan T, Fung HL: Vascular and hemodynamic differences between organic nitrates and nitrites. J Pharmacol Exp Ther. 1997 Jan;280(1):326-31. [PubMed:8996213 ]
  2. Ramanathan VM, Reigle TG, Muralidhara S, Dallas CE: Effects of acute inhalation exposure to isoamyl nitrite on the hypothalamo-pituitary-adrenal axis in male Sprague-Dawley rats. J Toxicol Environ Health A. 1998 Nov 13;55(5):345-58. [PubMed:9829558 ]
  3. Noack E, Feelisch M: Molecular mechanisms of nitrovasodilator bioactivation. Basic Res Cardiol. 1991;86 Suppl 2:37-50. [PubMed:1683227 ]