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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:39 UTC

HMDB ID

HMDB0001382

Secondary Accession Numbers

HMDB01382

Metabolite Identification

Common Name

Vaporole

Description

Isoamyl 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

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Methylbutanol nitrite	ChEBI
3-Methylbutyl nitrite	ChEBI
Amilnitrite	ChEBI
Amyl nitrite I	ChEBI
Amyl nitrosum	ChEBI
IPN	ChEBI
Isopentyl nitrite	ChEBI
Nitramyl	ChEBI
Nitrous acid, 3-methylbutyl ester	ChEBI
Nitrous acid, isopentyl ester	ChEBI
Pentyl nitrite	ChEBI
Isoamyl nitrite	Kegg
Aspiral	Kegg
Amyl nitrit	HMDB
Amyl nitrite (JP15/usp)	HMDB
Amyl nitrite	HMDB
Amyl nitrite(mixed isomers)	HMDB
Isopentyl ester nitrous acid	HMDB
Nitrite isopentyl alcohol	HMDB
Nitrous acid 3-methylbutyl ester	HMDB
Pentanoli nitris	HMDB
Vaporole amyl nitrite	HMDB
Vaporole	KEGG

Chemical Formula

C₅H₁₁NO₂

Average Molecular Weight

117.1463

Monoisotopic Molecular Weight

117.078978601

IUPAC Name

3-methylbutyl nitrite

Traditional Name

aspiral

CAS Registry Number

110-46-3

SMILES

CC(C)CCON=O

InChI Identifier

InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3

InChI Key

OWFXIOWLTKNBAP-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Organic nitroso compounds

Direct Parent

Organic 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 Framework

Aliphatic acyclic compounds

External Descriptors

nitrite esters (CHEBI:2691 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0001382)
Cell membrane (HMDB: HMDB0001382)

Not Available

Industrial application

Drug (HMDB: HMDB0001382)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	99.2 °C	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.88 g/L	ALOGPS
logP	1.87	ALOGPS
logP	2.16	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.66 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.63 m³·mol⁻¹	ChemAxon
Polarizability	12.63 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	125.25	31661259
DarkChem	[M-H]-	120.05	31661259
AllCCS	[M+H]+	126.168	32859911
AllCCS	[M-H]-	126.733	32859911
DeepCCS	[M+H]+	129.965	30932474
DeepCCS	[M-H]-	127.866	30932474
DeepCCS	[M-2H]-	163.884	30932474
DeepCCS	[M+Na]+	138.491	30932474
AllCCS	[M+H]+	126.2	32859911
AllCCS	[M+H-H2O]+	122.0	32859911
AllCCS	[M+NH4]+	130.1	32859911
AllCCS	[M+Na]+	131.2	32859911
AllCCS	[M-H]-	126.7	32859911
AllCCS	[M+Na-2H]-	130.0	32859911
AllCCS	[M+HCOO]-	133.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vaporole	CC(C)CCON=O	834.3	Standard polar	33892256
Vaporole	CC(C)CCON=O	678.4	Standard non polar	33892256
Vaporole	CC(C)CCON=O	843.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vaporole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-7cd42a07f3940a578b46	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vaporole 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaporole 10V, Positive-QTOF	splash10-01b9-8900000000-9952ab742a1e8ce49323	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaporole 20V, Positive-QTOF	splash10-00xr-9100000000-87ae2e9bdf1f4804ab30	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaporole 40V, Positive-QTOF	splash10-0ab9-9000000000-9bb6338451463c8db89c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaporole 10V, Negative-QTOF	splash10-014i-2900000000-7c5ed4be18f51fc3c515	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaporole 20V, Negative-QTOF	splash10-014i-9500000000-7d715aa0027b56813f45	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaporole 40V, Negative-QTOF	splash10-0a4j-9000000000-b6cdd36d8d07c5650074	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaporole 10V, Negative-QTOF	splash10-014r-7900000000-f488c41b56a34382a96b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaporole 20V, Negative-QTOF	splash10-0002-9000000000-a0441e6336543cb88423	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaporole 40V, Negative-QTOF	splash10-0002-9000000000-a0441e6336543cb88423	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaporole 10V, Positive-QTOF	splash10-01b9-9000000000-ec77cbf86b3d8ee8ad92	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaporole 20V, Positive-QTOF	splash10-05fr-9000000000-d2518b1e07a2fcd67eeb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vaporole 40V, Positive-QTOF	splash10-0006-9000000000-1f9d7edd509b1fd5b7c0	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

FDB022593

KNApSAcK ID

Not Available

Chemspider ID

7762

KEGG Compound ID

C07457

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vaporole

METLIN ID

Not Available

PubChem Compound

8053

PDB ID

Not Available

ChEBI ID

2691

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Wilson, 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

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 ]
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 ]
Noack E, Feelisch M: Molecular mechanisms of nitrovasodilator bioactivation. Basic Res Cardiol. 1991;86 Suppl 2:37-50. [PubMed:1683227 ]

Showing metabocard for Vaporole (HMDB0001382)

MOL for HMDB0001382 (Vaporole)

3D MOL for HMDB0001382 (Vaporole)

3D SDF for HMDB0001382 (Vaporole)

3D-SDF for HMDB0001382 (Vaporole)

PDB for HMDB0001382 (Vaporole)

3D PDB for HMDB0001382 (Vaporole)

SMILES for HMDB0001382 (Vaporole)

INCHI for HMDB0001382 (Vaporole)

Structure for HMDB0001382 (Vaporole)

3D Structure for HMDB0001382 (Vaporole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra