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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:56:15 UTC
Update Date2019-07-23 07:17:21 UTC
HMDB IDHMDB0061869
Secondary Accession Numbers
  • HMDB61869
Metabolite Identification
Common NameAcetonitrile
DescriptionAcetonitrile, also known as CH3-C#N or cyanomethane, belongs to the class of organic compounds known as nitriles. Nitriles are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N. Acetonitrile is the chemical compound with the formula CH3CN. Acetonitrile is possibly neutral. Acetonitrile is a potentially toxic compound. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Skin contact with cyanide salts can irritate and produce sores. Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death.
Structure
Data?1563866241
Synonyms
ValueSource
CH3-C#NChEBI
CyanomethaneChEBI
EthanenitrileChEBI
MeCNChEBI
Methyl cyanideChEBI
NCMeChEBI
Acetonitrile, 3H-labeledHMDB
Acetonitrile, 1-(14)C-labeledHMDB
Chemical FormulaC2H3N
Average Molecular Weight41.0519
Monoisotopic Molecular Weight41.026549101
IUPAC Nameacetonitrile
Traditional Nameacetonitrile
CAS Registry Number75-05-8
SMILES
CC#N
InChI Identifier
InChI=1S/C2H3N/c1-2-3/h1H3
InChI KeyWEVYAHXRMPXWCK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitriles. Nitriles are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassOrganic cyanides
Direct ParentNitriles
Alternative Parents
Substituents
  • Nitrile
  • Carbonitrile
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Environmental role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility26.1 g/LALOGPS
logP-0.04ALOGPS
logP-0.17ChemAxon
logS-0.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity11.62 m³·mol⁻¹ChemAxon
Polarizability4.27 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-44611647c11b54cc181fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-bf970518821dd2c06001Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-6af7455c7bc61c954070Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-836514fd6b54edefa88eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-44611647c11b54cc181fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-bf970518821dd2c06001Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-6af7455c7bc61c954070Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-836514fd6b54edefa88eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-6e1f4ab882eb15de3317Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-9f69695bfe2ad813c468Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-9f69695bfe2ad813c468Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-9f69695bfe2ad813c468Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-f33e0a1e80895824a9efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-f33e0a1e80895824a9efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f33e0a1e80895824a9efSpectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-6fc27dfe150133064bafSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetonitrile
METLIN IDNot Available
PubChem Compound6342
PDB IDNot Available
ChEBI ID38472
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hashimoto K: [Toxicology of acetonitrile]. Sangyo Igaku. 1991 Nov;33(6):463-74. [PubMed:1770614 ]
  2. Swanson JR, Krasselt WG: An acetonitrile-related death. J Forensic Sci. 1994 Jan;39(1):271-9. [PubMed:8113708 ]
  3. Strasser CE, Cronje S, Raubenheimer HG: (Acetonitrile-kappaN)penta-carbonyl-tungsten(0). Acta Crystallogr Sect E Struct Rep Online. 2011 Jun 1;67(Pt 6):m772. doi: 10.1107/S1600536811017879. Epub 2011 May 20. [PubMed:21754656 ]
  4. Seo DM, Boyle PD, Henderson WA: Tetra-kis(acetonitrile-kappaN)lithium hexa-fluoridophosphate acetonitrile monosolvate. Acta Crystallogr Sect E Struct Rep Online. 2011 Aug 1;67(Pt 8):m1148. doi: 10.1107/S1600536811027528. Epub 2011 Jul 30. [PubMed:22090907 ]
  5. Benmebarek S, Boudraa M, Bouacida S, Merazig H: 2-(2-Nitro-phenyl-sulfin-yl)acetonitrile. Acta Crystallogr Sect E Struct Rep Online. 2013 Mar 1;69(Pt 3):o432. doi: 10.1107/S1600536813004832. Epub 2013 Feb 23. [PubMed:23476603 ]
  6. Wikipedia [Link]
  7. Wikipedia [Link]
  8. August Van Gysel, Frans Soeterbroeck, Geert Vermeulen, 'Acetonitrile Recycling Process.' U.S. Patent US20080073201, issued March 27, 2008. [Link]
  9. Gisela Olive, Salvador Olive, 'Process for preparing acetonitrile.' U.S. Patent US4058548, issued February, 1976. [Link]
  10. Robert D. Presson, Hsin-Chih Wu, Edward J. Sockell, 'Continuous acetonitrile recovery process.' U.S. Patent US4362603, issued August, 1966. [Link]