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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:48 UTC

Update Date

2023-02-21 17:20:09 UTC

HMDB ID

HMDB0031239

Secondary Accession Numbers

HMDB31239

Metabolite Identification

Common Name

Ethyl nitrite

Description

Ethyl nitrite belongs to the class of organic compounds known as organic o-nitroso compounds. These are organic compounds containing a n-nitroso group -ON=O. Ethyl nitrite is an ether tasting compound. Based on a literature review very few articles have been published on Ethyl nitrite.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
SPIRIT OF nitrous ether	ChEMBL, HMDB
NITRE	ChEMBL, HMDB
SWEET spirit OF	ChEMBL, HMDB
Ethyl nitrite spirit	HMDB
Ethylester kyseliny dusite	HMDB
FEMA 2446	HMDB
Hyponitrous ether	HMDB
Nitrosyl ethoxide	HMDB
Nitrous acid, ethyl ester	HMDB
Nitrous ether	HMDB
Nitrous ethyl ether	HMDB
Spirit OF ethyl nitrite	HMDB
Sweet spirit OF niter	HMDB
Sweet spirit OF nitre	HMDB

Chemical Formula

C₂H₅NO₂

Average Molecular Weight

75.0666

Monoisotopic Molecular Weight

75.032028409

IUPAC Name

ethyl nitrite

Traditional Name

ethyl nitrite

CAS Registry Number

109-95-5

SMILES

CCON=O

InChI Identifier

InChI=1S/C2H5NO2/c1-2-5-3-4/h2H2,1H3

InChI Key

QQZWEECEMNQSTG-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

Organoleptic effect

Odor

Ether

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031239)
Cytoplasm (HMDB: HMDB0031239)

Source

Exogenous

Exogenous (HMDB: HMDB0031239)

Food

Food (HMDB: HMDB0031239)

Endogenous

Endogenous (HMDB: HMDB0031239)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031239)

Physical Properties

State

Liquid

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	50.7 g/L	ALOGPS
logP	0.42	ALOGPS
logP	0.9	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Basic)	-2.4	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	2	ChemAxon
Refractivity	17.95 m³·mol⁻¹	ChemAxon
Polarizability	6.79 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]+	113.964	31661259
DarkChem	[M-H]-	106.238	31661259
DeepCCS	[M+H]+	119.696	30932474
DeepCCS	[M-H]-	117.809	30932474
DeepCCS	[M-2H]-	153.109	30932474
DeepCCS	[M+Na]+	127.316	30932474
AllCCS	[M+H]+	120.8	32859911
AllCCS	[M+H-H2O]+	116.3	32859911
AllCCS	[M+NH4]+	125.0	32859911
AllCCS	[M+Na]+	126.3	32859911
AllCCS	[M-H]-	126.6	32859911
AllCCS	[M+Na-2H]-	132.1	32859911
AllCCS	[M+HCOO]-	138.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.33 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3246 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.97 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1369.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	512.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	211.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	374.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	175.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	429.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	537.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	331.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	909.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	334.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1030.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	353.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	647.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	496.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	170.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl nitrite	CCON=O	804.8	Standard polar	33892256
Ethyl nitrite	CCON=O	386.6	Standard non polar	33892256
Ethyl nitrite	CCON=O	589.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Ethyl nitrite EI-B (Non-derivatized)	splash10-003r-9000000000-88c8ffa4f735e44499c2	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl nitrite EI-B (Non-derivatized)	splash10-003r-9000000000-02ab86d458672b7fbb29	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl nitrite EI-B (Non-derivatized)	splash10-003r-9000000000-88c8ffa4f735e44499c2	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ethyl nitrite EI-B (Non-derivatized)	splash10-003r-9000000000-02ab86d458672b7fbb29	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl nitrite GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9000000000-169c090fede1be15063e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl 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 - Ethyl nitrite 10V, Positive-QTOF	splash10-004i-9000000000-1ae84828b6bc55206870	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl nitrite 20V, Positive-QTOF	splash10-004j-9000000000-aabf8c1374179e07c9ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl nitrite 40V, Positive-QTOF	splash10-004i-9000000000-52b047a2640f5e50c802	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl nitrite 10V, Negative-QTOF	splash10-00di-9000000000-2e640c55585dfc51c85e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl nitrite 20V, Negative-QTOF	splash10-00di-9000000000-08fdd8f7b68e0a92d89a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl nitrite 40V, Negative-QTOF	splash10-05fv-9000000000-c5039cbb7b3f9849ed87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl nitrite 10V, Positive-QTOF	splash10-004i-9000000000-6cd058429dff79d73c52	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl nitrite 20V, Positive-QTOF	splash10-004i-9000000000-fc33db11fdb6f217ef8c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl nitrite 40V, Positive-QTOF	splash10-0002-9000000000-f0922a415a539567bf02	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl nitrite 10V, Negative-QTOF	splash10-00di-9000000000-7a3b3d89a0ae19b4c8c3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl nitrite 20V, Negative-QTOF	splash10-0002-9000000000-a0441e6336543cb88423	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl nitrite 40V, Negative-QTOF	splash10-0002-9000000000-9628ab69369c74bd1df3	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB003266

KNApSAcK ID

Not Available

Chemspider ID

7735

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethyl nitrite

METLIN ID

Not Available

PubChem Compound

8026

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1312811

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Gago B, Nystrom T, Cavaleiro C, Rocha BS, Barbosa RM, Laranjinha J, Lundberg JO: The potent vasodilator ethyl nitrite is formed upon reaction of nitrite and ethanol under gastric conditions. Free Radic Biol Med. 2008 Aug 15;45(4):404-12. doi: 10.1016/j.freeradbiomed.2008.04.027. Epub 2008 Apr 26. [PubMed:18482590 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Ethyl nitrite (HMDB0031239)

MOL for HMDB0031239 (Ethyl nitrite)

3D MOL for HMDB0031239 (Ethyl nitrite)

3D SDF for HMDB0031239 (Ethyl nitrite)

3D-SDF for HMDB0031239 (Ethyl nitrite)

PDB for HMDB0031239 (Ethyl nitrite)

3D PDB for HMDB0031239 (Ethyl nitrite)

SMILES for HMDB0031239 (Ethyl nitrite)

INCHI for HMDB0031239 (Ethyl nitrite)

Structure for HMDB0031239 (Ethyl nitrite)

3D Structure for HMDB0031239 (Ethyl nitrite)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra