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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:21 UTC

Update Date

2023-02-21 17:20:24 UTC

HMDB ID

HMDB0031329

Secondary Accession Numbers

HMDB31329

Metabolite Identification

Common Name

Butyl nitrite

Description

Butyl 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

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Butyl ester OF nitrous acid	HMDB
N-Butyl nitrite	HMDB, MeSH
N-C4H9ONO	HMDB
NBN	HMDB
Nitrous acid, butyl ester	HMDB
Nitrous acid, N-butyl ester	HMDB
N-Butyl nitrite, 15N-labeled	MeSH, HMDB

Chemical Formula

C₄H₉NO₂

Average Molecular Weight

103.1198

Monoisotopic Molecular Weight

103.063328537

IUPAC Name

butyl nitrite

Traditional Name

butyl nitrite

CAS Registry Number

544-16-1

SMILES

CCCCON=O

InChI Identifier

InChI=1S/C4H9NO2/c1-2-3-4-7-5-6/h2-4H2,1H3

InChI Key

JQJPBYFTQAANLE-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031329)
Cytoplasm (HMDB: HMDB0031329)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031329)

Source

Endogenous

Endogenous (HMDB: HMDB0031329)

Exogenous

Food

Food (HMDB: HMDB0031329)

Exogenous (HMDB: HMDB0031329)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	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	12.8 g/L	ALOGPS
logP	1.44	ALOGPS
logP	1.87	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Basic)	-2	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	27.08 m³·mol⁻¹	ChemAxon
Polarizability	10.8 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]+	120.624	31661259
DarkChem	[M-H]-	115.579	31661259
DeepCCS	[M+H]+	127.81	30932474
DeepCCS	[M-H]-	125.914	30932474
DeepCCS	[M-2H]-	161.394	30932474
DeepCCS	[M+Na]+	135.819	30932474
AllCCS	[M+H]+	123.2	32859911
AllCCS	[M+H-H2O]+	118.8	32859911
AllCCS	[M+NH4]+	127.2	32859911
AllCCS	[M+Na]+	128.4	32859911
AllCCS	[M-H]-	121.3	32859911
AllCCS	[M+Na-2H]-	125.1	32859911
AllCCS	[M+HCOO]-	129.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butyl nitrite	CCCCON=O	799.5	Standard polar	33892256
Butyl nitrite	CCCCON=O	576.7	Standard non polar	33892256
Butyl nitrite	CCCCON=O	778.9	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 - Butyl nitrite GC-MS (Non-derivatized) - 70eV, Positive	splash10-06vl-9000000000-60606d4dbf82f88007db	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl nitrite 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 - Butyl nitrite 10V, Positive-QTOF	splash10-0zfr-8900000000-e1313c313380813bcc07	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl nitrite 20V, Positive-QTOF	splash10-0a4i-9100000000-7a38f300a34930eb8750	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl nitrite 40V, Positive-QTOF	splash10-0a4l-9000000000-7451dcfde52132f82a8d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl nitrite 10V, Negative-QTOF	splash10-0udi-2900000000-19eecc20b814f985eb68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl nitrite 20V, Negative-QTOF	splash10-0zfr-9500000000-db3a77751ebc808f3477	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl nitrite 40V, Negative-QTOF	splash10-000g-9000000000-bc9b4764dc8a20525551	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl nitrite 10V, Positive-QTOF	splash10-0a4i-9000000000-b4e932a5ebfdb66601cb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl nitrite 20V, Positive-QTOF	splash10-0a4i-9000000000-a80e9b0fd0ed5ca6c528	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl nitrite 40V, Positive-QTOF	splash10-0a4i-9000000000-db8392b5b998f0490a67	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl nitrite 10V, Negative-QTOF	splash10-0udi-2900000000-0e854c5eae20c8f3cffc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl nitrite 20V, Negative-QTOF	splash10-0002-9000000000-a0441e6336543cb88423	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl nitrite 40V, Negative-QTOF	splash10-0002-9000000000-210d2a10319099076cf3	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

Cytoplasm
Extracellular

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

FDB003391

KNApSAcK ID

Not Available

Chemspider ID

10530

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Butyl nitrite

METLIN ID

Not Available

PubChem Compound

10996

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Butyl nitrite (HMDB0031329)

MOL for HMDB0031329 (Butyl nitrite)

3D MOL for HMDB0031329 (Butyl nitrite)

3D SDF for HMDB0031329 (Butyl nitrite)

3D-SDF for HMDB0031329 (Butyl nitrite)

PDB for HMDB0031329 (Butyl nitrite)

3D PDB for HMDB0031329 (Butyl nitrite)

SMILES for HMDB0031329 (Butyl nitrite)

INCHI for HMDB0031329 (Butyl nitrite)

Structure for HMDB0031329 (Butyl nitrite)

3D Structure for HMDB0031329 (Butyl nitrite)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra