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

Molecular Formula C5H5NO2
Molecular Weight 111.0987
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Airborne concentrations of ethyl and methyl cyanoacrylate in the workplace.
2001 Jan-Feb
Surgical glue and necrosis of arterial wall.
2003 Mar
[Hygienic standards of the occupational air quality established by the Experts on Chemical Agents, 2002].
2004
[Occupational asthma due to cyanoacrylate: a case-report].
2004 Nov-Dec
Influence of cervical preflaring on determination of apical file size in maxillary molars: SEM analysis.
2005
Spectroscopic studies of rhodamine 6G dispersed in polymethylcyanoacrylate.
2005 Feb
A novel coating biomaterial for intracranial aneurysms: effects and safety in extra- and intracranial carotid artery.
2005 Mar
A morphometric, neuroanatomical, and behavioral study on the effects of geometric constraint on the growing brain: the methyl 2-cyanoacrylate craniosynostosis model.
2005 May
A mechanistic model for the superglue fuming of latent fingerprints.
2006 Nov
Case of the month: Honey I glued the kids: tissue adhesives are not the same as "superglue".
2007 Mar
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:53:34 UTC 2023
Edited
by admin
on Sat Dec 16 17:53:34 UTC 2023
Record UNII
WN7979561R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MECRYLATE
HSDB   USAN  
USAN  
Official Name English
Methyl 2-cyanoacrylate
Systematic Name English
MECRILATE [MART.]
Common Name English
MECRILATE
INN   MART.  
INN  
Official 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 Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY
HSDB
1207
Created by admin on Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY
MERCK INDEX
m7387
Created by admin on Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID4025589
Created by admin on Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY
PUBCHEM
8711
Created by admin on Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY
INN
2752
Created by admin on Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY
FDA UNII
WN7979561R
Created by admin on Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY
WIKIPEDIA
Methyl cyanoacrylate
Created by admin on Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY
ChEMBL
CHEMBL2106424
Created by admin on Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY
EVMPD
SUB08687MIG
Created by admin on Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-275-2
Created by admin on Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY
MESH
C008424
Created by admin on Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY
CAS
137-05-3
Created by admin on Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY
SMS_ID
100000081987
Created by admin on Sat Dec 16 17:53:34 UTC 2023 , Edited by admin on Sat Dec 16 17:53:34 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY