U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C2H3NO
Molecular Weight 57.0513
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of METHYL ISOCYANATE

SMILES

CN=C=O

InChI

InChIKey=HAMGRBXTJNITHG-UHFFFAOYSA-N
InChI=1S/C2H3NO/c1-3-2-4/h1H3

HIDE SMILES / InChI

Molecular Formula C2H3NO
Molecular Weight 57.0513
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Methyl isocyanate (MIC) is a noxious industrial chemical used extensively in the production of carbamate pesticides. This compound is a respiratory toxicant. Recently published studies have shown that methyl isocyanate can lead to epigenetic alterations due to its strong binding with DNA methyltransferase 1 (DNMT1) which is responsible for maintenance of normal methylation, cell growth and survival in mammals.

Approval Year

PubMed

PubMed

TitleDatePubMed
Non-heme dioxygenase catalyzes atypical oxidations of 6,7-bicyclic systems to form the 6,6-quinolone core of viridicatin-type fungal alkaloids.
2014-11-17
Cell cycle deregulation by methyl isocyanate: Implications in liver carcinogenesis.
2014-03
Molecular mechanisms of isocyanate induced oncogenic transformation in ovarian epithelial cells.
2010-11
2,2-Dimethyl-1,3-benzodioxol-4-yl N-methyl-carbamate.
2010-09-18
25 years after the Bhopal gas tragedy.
2010-09-16
[The Bhopal tragedy 25 (10+15) years after].
2010-09-11
Effects of exposure of parents to toxic gases in Bhopal on the offspring.
2010-08
Aromatic substitution reactions between ionized benzene derivatives and neutral methyl isocyanide.
2010-07-15
Bhopal. India launches new probe of cyanide disaster.
2010-07-02
Triage, monitoring, and treatment of mass casualty events involving chemical, biological, radiological, or nuclear agents.
2010-07
Sensory detection and responses to toxic gases: mechanisms, health effects, and countermeasures.
2010-07
Adsorption efficiency of respirator filter cartridges for isocyanates.
2010-06
Regulation of isocyanate-induced apoptosis, oxidative stress, and inflammation in cultured human neutrophils: isocyanate-induced neutrophils apoptosis.
2010-06
A new general pathway for synthesis of reference compounds of N-terminal valine-isocyanate adducts.
2010-03-15
Different experimental approaches in modelling cataractogenesis: An overview of selenite-induced nuclear cataract in rats.
2010-03
Investigating genetic outcomes following 1984 Toxic Union Carbide disaster in India: epidemiological challenges.
2010
Molecular characterization of isocyanate-induced male germ-line genomic instability.
2010
Status of inflammatory biomarkers in the population that survived the Bhopal gas tragedy: a study after two decades.
2010
The interaction of zinc(II) and hydroxamic acids and a metal-triggered Lossen rearrangement.
2009-12-14
A submarine journey: the pyrrole-imidazole alkaloids.
2009-11-27
Correlation of aberrant expression of p53, Rad50, and cyclin-E proteins with microsatellite instability in gallbladder adenocarcinomas.
2009-10-06
Clinical activity of laromustine (Onrigin™) in hematologic malignancies.
2009-10
An in vitro evaluation of the victim and perpetrator potential of the anticancer agent laromustine (VNP40101M), based on reaction phenotyping and inhibition and induction of cytochrome P450 enzymes.
2009-09
Mitochondrial oxidative stress elicits chromosomal instability after exposure to isocyanates in human kidney epithelial cells.
2009-08
Induction of genomic instability in cultured human colon epithelial cells following exposure to isocyanates.
2009-06
Respiratory symptoms and lung function in foundry workers exposed to low molecular weight isocyanates.
2009-06
Analysis of cellular response to isocyanate using N-succinimidyl N-methylcarbamate exposure in cultured mammalian cells.
2009-05
In utero exposure to methyl isocyanate in the Bhopal gas disaster: evidence of persisting hyperactivation of immune system two decades later.
2009-04
Identification and fragmentation pathways of caffeine metabolites in urine samples via liquid chromatography with positive electrospray ionization coupled to a hybrid quadrupole linear ion trap (LTQ) and Fourier transform ion cyclotron resonance mass spectrometry and tandem mass spectrometry.
2009-04
Transient receptor potential ankyrin 1 antagonists block the noxious effects of toxic industrial isocyanates and tear gases.
2009-04
Inflammatory response to isocyanates and onset of genomic instability in cultured human lung fibroblasts.
2009-02-10
Laromustine, a sulfonyl hydrolyzing alkylating prodrug for cancer therapy.
2009-01
Bhopal Gas Tragedy: review of clinical and experimental findings after 25 years.
2009
Rats repeatedly exposed to toluene diisocyanate exhibit immune reactivity against methyl isocyanate-protein conjugates.
2009
Isocyanates induces DNA damage, apoptosis, oxidative stress, and inflammation in cultured human lymphocytes.
2008-12-30
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl N-methyl-carbamate.
2008-12-13
A case of isocyanate-induced asthma possibly complicated by food allergy after peanut consumption: a case report.
2008-11-26
Validation of transferability of DBA derivatization and LC-MS/MS determination method for isocyanates via an interlaboratory comparison.
2008-11
Initial testing of VNP40101M (Cloretazine) by the pediatric preclinical testing program.
2008-09
Aftermath of the Bhopal accident.
2008-06-07
Representation and re-presentation in litigation science.
2008-01
Overseas experience in global health: travels to Bhopal, India, 20 years after the Union Carbide disaster.
2008-01
Building capacity to address emerging problems in developing countries: intentional self-poisoning and pesticides.
2008
Evaluation and application of the RD50 for determining acceptable exposure levels of airborne sensory irritants for the general public.
2007-11
Abstracts of papers presented at the 2007 pittsburgh conference.
2007
Binding of [1-14C]methyl isocyanate to erythrocyte membrane proteins.
1996-03-01
Chronic lung inflammation in victims of toxic gas leak at Bhopal.
1995-02
Influence of methylamine and N,N'-dimethylurea, the hydrolysis products of methyl isocyanate, on its systemic toxicity.
1993-01-01
The antibody response to methyl isocyanate: experimental and clinical findings.
1987-06
Use of hexyl isocyanate antigen to detect antibodies to hexamethylene diisocyanate (HDI) in sensitized guinea pigs and in a sensitized worker.
1982-05-01
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:40:26 GMT 2025
Edited
by admin
on Mon Mar 31 18:40:26 GMT 2025
Record UNII
C588JJ4BV9
Record Status Validated (UNII)
Record Version
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Name Type Language
METHYL ISOCYANATE
HSDB   MI  
Systematic Name English
NSC-64323
Preferred Name English
METHYL ISOCYANATE [HSDB]
Common Name English
METHANE, ISOCYANATO-
Systematic Name English
METHYL ISOCYANATE [MI]
Common Name English
ISOCYANIC ACID, METHYL ESTER
Common Name English
MIC
Common Name English
Code System Code Type Description
CAS
624-83-9
Created by admin on Mon Mar 31 18:40:26 GMT 2025 , Edited by admin on Mon Mar 31 18:40:26 GMT 2025
PRIMARY
ECHA (EC/EINECS)
210-866-3
Created by admin on Mon Mar 31 18:40:26 GMT 2025 , Edited by admin on Mon Mar 31 18:40:26 GMT 2025
PRIMARY
MERCK INDEX
m7431
Created by admin on Mon Mar 31 18:40:26 GMT 2025 , Edited by admin on Mon Mar 31 18:40:26 GMT 2025
PRIMARY Merck Index
PUBCHEM
12228
Created by admin on Mon Mar 31 18:40:26 GMT 2025 , Edited by admin on Mon Mar 31 18:40:26 GMT 2025
PRIMARY
DRUG BANK
DB12765
Created by admin on Mon Mar 31 18:40:26 GMT 2025 , Edited by admin on Mon Mar 31 18:40:26 GMT 2025
PRIMARY
MESH
C008461
Created by admin on Mon Mar 31 18:40:26 GMT 2025 , Edited by admin on Mon Mar 31 18:40:26 GMT 2025
PRIMARY
FDA UNII
C588JJ4BV9
Created by admin on Mon Mar 31 18:40:26 GMT 2025 , Edited by admin on Mon Mar 31 18:40:26 GMT 2025
PRIMARY
NSC
64323
Created by admin on Mon Mar 31 18:40:26 GMT 2025 , Edited by admin on Mon Mar 31 18:40:26 GMT 2025
PRIMARY
EPA CompTox
DTXSID1023786
Created by admin on Mon Mar 31 18:40:26 GMT 2025 , Edited by admin on Mon Mar 31 18:40:26 GMT 2025
PRIMARY
WIKIPEDIA
Methyl isocyanate
Created by admin on Mon Mar 31 18:40:26 GMT 2025 , Edited by admin on Mon Mar 31 18:40:26 GMT 2025
PRIMARY
HSDB
1165
Created by admin on Mon Mar 31 18:40:26 GMT 2025 , Edited by admin on Mon Mar 31 18:40:26 GMT 2025
PRIMARY