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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:57 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?1563860697
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
AspiralKegg
Isoamyl nitriteKegg
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
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point99.2 °CNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-7cd42a07f3940a578b46JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-8900000000-9952ab742a1e8ce49323JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-9100000000-87ae2e9bdf1f4804ab30JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-9bb6338451463c8db89cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-7c5ed4be18f51fc3c515JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9500000000-7d715aa0027b56813f45JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-9000000000-b6cdd36d8d07c5650074JSpectraViewer | MoNA
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
FoodDB 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
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 ]