Record Information
Version1.0
Creation Date2009-03-06 18:58:08 UTC
Update Date2026-04-05 16:43:58 UTC
Accession NumberCHEM000123
Identification
Common NameHydrogen cyanide
ClassSmall Molecule
DescriptionHydrogen cyanide (with the historical common name of Prussic acid) is a chemical compound with chemical formula HCN. It is a colorless, extremely poisonous liquid that boils slightly above room temperature at 26 C (79ЎF). A hydrogen cyanide concentration of 300 mg/m3 in air will kill a human within 10Р60 minutes.[38] A hydrogen cyanide concentration of 3500 ppm (about 3200 mg/m3) will kill a human in about 1 minute.[38] The toxicity is caused by the cyanide ion, which halts cellular respiration by acting as a non-competitive inhibitor for an enzyme in mitochondria called cytochrome c oxidase.
Contaminant Sources
  • Clean Air Act Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • OSHA Hazardous Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
Contaminant Type
  • Cyanide Compound
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Nitrile
  • Organic Compound
  • Pollutant
Chemical Structure
Thumb
Synonyms
ValueSource
[CHN]ChEBI
BlausaeureChEBI
CyanwasserstoffChEBI
FormonitrileChEBI
HCNChEBI
Hydrocyanic acidChEBI
CyanideKegg
HydrocyanateGenerator
Zyklon bHMDB
Cyanide, hydrogenHMDB
Acid, hydrocyanicHMDB
Chemical FormulaCHN
Average Molecular Mass27.025 g/mol
Monoisotopic Mass27.011 g/mol
CAS Registry Number74-90-8
IUPAC Nameformonitrile
Traditional Namehydrogen cyanide
SMILESC#N
InChI IdentifierInChI=1S/CHN/c1-2/h1H
InChI KeyLELOWRISYMNNSU-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
  • Carbonitrile
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless gas or liquid.
Experimental Properties
PropertyValue
Melting Point-13.4°C
Boiling PointNot Available
Solubility1000 mg/mL at 25 °C [METCALF,RL (1978)]
Predicted Properties
PropertyValueSource
Water Solubility3.26 g/LALOGPS
logP-0.65ALOGPS
logP-0.35ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity7.01 m³·mol⁻¹ChemAxon
Polarizability2.31 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-74b665f5c9189546344aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-4292bd1fdf6103a76243Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-4292bd1fdf6103a76243Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-4292bd1fdf6103a76243Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-e4243e331f99da46857aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-e4243e331f99da46857aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-e4243e331f99da46857aSpectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9000000000-ff23e89c9d09e6b92cbcSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (2) ; inhalation (2) ; dermal (2)
Mechanism of ToxicityOrganic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (3)
MetabolismOrganic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (2)
Toxicity ValuesLD50: 3700 ug/kg (Subcutaneous, Rat) (N010) LD50: 810 ug/kg (Intravenous, Rat) LD50: 3700 ug/kg (Oral, Mouse) LD50: 2990 ug/kg (Intraperitoneal, Mouse) LC50: 142 ppm over 30 minutes (Inhalation, Rat) (5)
Lethal Dose50 to 60 mg (oral) or 270 ppm (inhaled for an adult human. (6, 7)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesHydrogen cyanide is a precursor to many chemical compounds, ranging from polymers to pharmaceuticals. (4)
Minimum Risk LevelNot Available
Health EffectsExposure 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. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (2, 3)
SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (2, 3)
TreatmentAntidotes 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. Oxygen therapy can also be administered. (3)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0060292
FooDB IDFDB014486
Phenol Explorer IDNot Available
KNApSAcK IDC00007569
BiGG IDNot Available
BioCyc IDHCN
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHydrogen_cyanide
Chemspider ID748
ChEBI ID18407
PubChem Compound ID768
Kegg Compound IDC01326
YMDB IDNot Available
ECMDB IDECMDB21231
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19849830
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=26700190
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26778429
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26823582
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26940198
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=27123778
7. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3.