Showing Compound Card for Methyl isocyanate  (CDB000626)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:47:20 UTC
Updated at2020-11-18 16:35:21 UTC
CannabisDB IDCDB000626
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMethyl isocyanate 
DescriptionIsocyanatomethane or methyl isocyanate, also known as iso-cyanatomethane or methyl carbonimide, belongs to the class of organic compounds known as isocyanates. These are organic compounds containing the isocyanic acid tautomer, HN=C=O, of cyanic acid, HOCN or its hydrocarbyl derivatives RN=C=O. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Isocyanatomethane is a colorless, poisonous, lachrymatory (tearing agent), flammable liquid. It is soluble in water, but it also reacts with it. Isocyanatomethane is an intermediate in the production of carbamate pesticides (such as carbaryl, carbofuran, methomyl, and aldicarb). It has also been used in the production of rubbers and adhesives. As a highly toxic and irritating material, it is extremely hazardous to human health. Cyanide is an inhibitor of the cytochrome C oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). As a result, the electron transport chain is disrupted, and the cell can no longer aerobically produce ATP for energy. 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. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Isocyanatomethane has been detected in the volatile fraction of Cannabis sativa samples, obtained from police seizures (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Iso-cyanatomethaneChEBI
Isocyanate de methyleChEBI
IsocyanatomethaneChEBI
Methyl carbonimideChEBI
Methyl isocyanideChEBI
MethylcarbylamineChEBI
MICChEBI
Isocyanic acid de methyleGenerator
Methyl isocyanic acidGenerator
MethylisocyanateMeSH
Chemical FormulaC2H3NO
Average Molecular Weight57.05
Monoisotopic Molecular Weight57.0215
IUPAC Nameisocyanatomethane
Traditional Namemethyl isocyanate
CAS Registry Number30108-95-3
SMILES
CN=C=O
InChI Identifier
InChI=1S/C2H3NO/c1-3-2-4/h1H3
InChI KeyHAMGRBXTJNITHG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isocyanates. These are organic compounds containing the isocyanic acid tautomer, HN=C=O, of cyanic acid, HOC#N or its hydrocarbyl derivatives RN=C=O.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassIsocyanates
Direct ParentIsocyanates
Alternative Parents
Substituents
  • Isocyanate
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.24ALOGPS
logP-0.043ChemAxon
logS-0.19ALOGPS
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity13.34 m³·mol⁻¹ChemAxon
Polarizability5.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9000000000-bac75d607afdfaf42e3b2014-09-20View Spectrum
Predicted GC-MSMethyl isocyanate , non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethyl isocyanate , non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-537d087394e5c945727c2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-2a3cdc209f4259f4c82f2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-fde849bd92cb4861eeb92016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-17d207ce7aad8e563f462016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-310d4782599e1f82e42b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9000000000-95d034393a0bc3735c0c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-13480378ef45df0bc7d72021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-13480378ef45df0bc7d72021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-13480378ef45df0bc7d72021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-b549c8ecd4164bcd85c02021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-b549c8ecd4164bcd85c02021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-b549c8ecd4164bcd85c02021-10-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDDB12765
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 LinkMethyl isocyanate
METLIN IDNot Available
PubChem Compound12228
PDB IDNot Available
ChEBI ID59059
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]