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

Details

Stereochemistry ACHIRAL
Molecular Formula C5H5NO2
Molecular Weight 111.0987
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MECRYLATE

SMILES

COC(=O)C(=C)C#N

InChI

InChIKey=MWCLLHOVUTZFKS-UHFFFAOYSA-N
InChI=1S/C5H5NO2/c1-4(3-6)5(7)8-2/h1H2,2H3

HIDE SMILES / InChI
Mecrylate (metyl 2-cyanoacrylate) ) is a clear, colorless liquid with a strong, acrid odor. In contact with hydroxide ions (liquids like blood or water, air humidity), the cyanoacrylates form long, strong and waterproof chains in an exothermic reaction. The resulting polymer leads to a stable adhesive bond. It may be used as tissue adhesive in surgery. Mecrylate is the first generation short-chain cyanoacrylate, it turned out to be histotoxic and caused distinct foreign-body reactions.

Approval Year

PubMed

PubMed

TitleDatePubMed
Case of the month: Honey I glued the kids: tissue adhesives are not the same as "superglue".
2007-03
A mechanistic model for the superglue fuming of latent fingerprints.
2006-11
A morphometric, neuroanatomical, and behavioral study on the effects of geometric constraint on the growing brain: the methyl 2-cyanoacrylate craniosynostosis model.
2005-05
[Occupational asthma due to cyanoacrylate: a case-report].
2005-03-01
A novel coating biomaterial for intracranial aneurysms: effects and safety in extra- and intracranial carotid artery.
2005-03
Spectroscopic studies of rhodamine 6G dispersed in polymethylcyanoacrylate.
2005-02
Influence of cervical preflaring on determination of apical file size in maxillary molars: SEM analysis.
2005
[Hygienic standards of the occupational air quality established by the Experts on Chemical Agents, 2002].
2004
Surgical glue and necrosis of arterial wall.
2003-03
Airborne concentrations of ethyl and methyl cyanoacrylate in the workplace.
2001-03-22
Name Type Language
MECRILATE
INN   MART.  
INN  
Preferred Name English
MECRYLATE
HSDB   USAN  
USAN  
Official Name English
Methyl 2-cyanoacrylate
Systematic Name English
MECRILATE [MART.]
Common Name English
METHYL CYANOACRYLATE [MI]
Common Name English
2-PROPENOIC ACID, 2-CYANO-, METHYL ESTER
Common Name English
CYANOACRYLATE METHYL ESTER
Systematic Name English
MECRYLATE [USAN]
Common Name English
ARON ALPHA A
Brand Name English
MECRYLATE [HSDB]
Common Name English
mecrilate [INN]
Common Name English
Mecrilate [WHO-DD]
Common Name English
Code System Code Type Description
NCI_THESAURUS
C174934
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
PRIMARY
HSDB
1207
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
PRIMARY
MERCK INDEX
m7387
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID4025589
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
PRIMARY
PUBCHEM
8711
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
PRIMARY
INN
2752
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
PRIMARY
FDA UNII
WN7979561R
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
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WIKIPEDIA
Methyl cyanoacrylate
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
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ChEMBL
CHEMBL2106424
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
PRIMARY
EVMPD
SUB08687MIG
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
PRIMARY
ECHA (EC/EINECS)
205-275-2
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
PRIMARY
MESH
C008424
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
PRIMARY
CAS
137-05-3
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
PRIMARY
SMS_ID
100000081987
Created by admin on Wed Apr 02 09:43:34 GMT 2025 , Edited by admin on Wed Apr 02 09:43:34 GMT 2025
PRIMARY