CHEBI:7514 - neostigmine

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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.
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Formula C12H19N2O2
Net Charge +1
Average Mass 223.29150
Monoisotopic Mass 223.145
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.
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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
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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.