CHEBI:3172 - bretylium

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ChEBI Name bretylium
ChEBI ID CHEBI:3172
Definition A quaternary ammonium cation having 2-bromobenzyl, ethyl and two methyl groups attached to the nitrogen. It blocks noradrenaline release from the peripheral sympathetic nervous system, and is used in emergency medicine, cardiology, and other specialties for the acute management of ventricular tachycardia and ventricular fibrillation.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C11H17BrN
Net Charge +1
Average Mass 243.16300
Monoisotopic Mass 242.05389
InChI InChI=1S/C11H17BrN/c1-4-13(2,3)9-10-7-5-6-8-11(10)12/h5-8H,4,9H2,1-3H3/q+1
InChIKey AAQOQKQBGPPFNS-UHFFFAOYSA-N
SMILES CC[N+](C)(C)Cc1ccccc1Br
Roles Classification
Biological Role(s): adrenergic antagonist
An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
Application(s): adrenergic antagonist
An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
anti-arrhythmia drug
A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
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ChEBI Ontology
Outgoing bretylium (CHEBI:3172) has role adrenergic antagonist (CHEBI:37887)
bretylium (CHEBI:3172) has role anti-arrhythmia drug (CHEBI:38070)
bretylium (CHEBI:3172) has role antihypertensive agent (CHEBI:35674)
bretylium (CHEBI:3172) is a quaternary ammonium ion (CHEBI:35267)
Incoming bretylium tosylate (CHEBI:3173) has part bretylium (CHEBI:3172)
IUPAC Name
N-(2-bromobenzyl)-N,N-dimethylethanaminium
Synonyms Sources
(2-bromobenzyl)ethyldimethylaminium ChEBI
2-bromo-N-ethyl-N,N-dimethylbenzenemethanaminium ChEBI
N-ethyl-N,N-dimethyl-2-bromobenzenemethanaminium ChEBI
Manual Xrefs Databases
394 DrugCentral
Bretylium Wikipedia
C06855 KEGG COMPOUND
DB01158 DrugBank
LSM-5607 LINCS
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Registry Numbers Types Sources
4135284 Beilstein Registry Number Beilstein
59-41-6 CAS Registry Number ChemIDplus
Last Modified
22 February 2017