Cannabis Compound Database: Showing Compound Card for Methyl isocyanate (CDB000626)

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Record Information

Version

1.0

Created at

2020-03-19 00:47:20 UTC

Updated at

2020-11-18 16:35:21 UTC

CannabisDB ID

CDB000626

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Methyl isocyanate

Description

Isocyanatomethane 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Iso-cyanatomethane	ChEBI
Isocyanate de methyle	ChEBI
Isocyanatomethane	ChEBI
Methyl carbonimide	ChEBI
Methyl isocyanide	ChEBI
Methylcarbylamine	ChEBI
MIC	ChEBI
Isocyanic acid de methyle	Generator
Methyl isocyanic acid	Generator
Methylisocyanate	MeSH

Chemical Formula

C₂H₃NO

Average Molecular Weight

57.05

Monoisotopic Molecular Weight

57.0215

IUPAC Name

isocyanatomethane

Traditional Name

methyl isocyanate

CAS Registry Number

30108-95-3

SMILES

CN=C=O

InChI Identifier

InChI=1S/C2H3NO/c1-3-2-4/h1H3

InChI Key

HAMGRBXTJNITHG-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Isocyanates

Direct Parent

Isocyanates

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 Framework

Aliphatic acyclic compounds

External Descriptors

isocyanates (CHEBI:59059 )

Ontology

Role

Indirect biological role:

Toxin

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
logP	-0.24	ALOGPS
logP	-0.043	ChemAxon
logS	-0.19	ALOGPS
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.43 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	13.34 m³·mol⁻¹	ChemAxon
Polarizability	5.05 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9000000000-bac75d607afdfaf42e3b	2014-09-20	View Spectrum
Predicted GC-MS	Methyl isocyanate , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methyl isocyanate , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-537d087394e5c945727c	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-2a3cdc209f4259f4c82f	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-fde849bd92cb4861eeb9	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-17d207ce7aad8e563f46	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-310d4782599e1f82e42b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-9000000000-95d034393a0bc3735c0c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-13480378ef45df0bc7d7	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-13480378ef45df0bc7d7	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-13480378ef45df0bc7d7	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-b549c8ecd4164bcd85c0	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-b549c8ecd4164bcd85c0	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-b549c8ecd4164bcd85c0	2021-10-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

Not Available

DrugBank ID

DB12765

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methyl isocyanate

METLIN ID

Not Available

PubChem Compound

12228

PDB ID

Not Available

ChEBI ID

59059

References

General References

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 ]

Showing Compound Card for Methyl isocyanate (CDB000626)

Structure for CDB000626 (Methyl isocyanate )