CHEBI:7514 - neostigmine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name neostigmine
ChEBI ID CHEBI:7514
Definition A quaternary ammonium ion comprising an anilinium ion core having three methyl substituents on the aniline nitrogen, and a 3-[(dimethylcarbamoyl)oxy] substituent at position 3. It is a parasympathomimetic which acts as a reversible acetylcholinesterase inhibitor.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C12H19N2O2
Net Charge +1
Average Mass 223.29150
Monoisotopic Mass 223.14410
InChI InChI=1S/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5/h6-9H,1-5H3/q+1
InChIKey ALWKGYPQUAPLQC-UHFFFAOYSA-N
SMILES CN(C)C(=O)Oc1cccc(c1)[N+](C)(C)C
Roles Classification
Biological Role(s): EC 3.1.1.7 (acetylcholinesterase) inhibitor
An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
Application(s): antidote to curare poisoning
A role borne by a molecule that acts to counteract or neutralize the deleterious effects of curare.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing neostigmine (CHEBI:7514) has role antidote to curare poisoning (CHEBI:74530)
neostigmine (CHEBI:7514) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
neostigmine (CHEBI:7514) is a quaternary ammonium ion (CHEBI:35267)
Incoming neostigmine bromide (CHEBI:179557) has part neostigmine (CHEBI:7514)
IUPAC Name
3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium
Synonyms Sources
(m-Hydroxyphenyl)trimethylammonium dimethylcarbamate ChemIDplus
3-Trimethylammoniumphenyl N,N-dimethylcarbamate ChemIDplus
Eustigmin ChemIDplus
Eustigmine ChemIDplus
m-Trimethylammoniumphenyldimethylcarbamate ChemIDplus
Prostigmine ChemIDplus
Vagostigmine ChemIDplus
Manual Xrefs Databases
1897 DrugCentral
C07258 KEGG COMPOUND
D08261 KEGG DRUG
DB01400 DrugBank
HMDB0015472 HMDB
LSM-5360 LINCS
Neostigmine Wikipedia
View more database links
Registry Numbers Types Sources
3615946 Reaxys Registry Number Reaxys
3615946 Beilstein Registry Number ChemIDplus
59-99-4 CAS Registry Number KEGG COMPOUND
59-99-4 CAS Registry Number NIST Chemistry WebBook
59-99-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
7200780 PubMed citation Europe PMC
8584207 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2014-06-10 Neostigmine can be found in blood and urine samples of individuals who have taken this drug.