CHEBI:6916 - mexiletine

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ChEBI Name mexiletine
ChEBI ID CHEBI:6916
Definition An aromatic ether which is 2,6-dimethylphenyl ether of 2-aminopropan-1-ol.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:115958
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Formula C11H17NO
Net Charge 0
Average Mass 179.25880
Monoisotopic Mass 179.131
InChI InChI=1S/C11H17NO/c1-8-5-4-6-9(2)11(8)13-7-10(3)12/h4-6,10H,7,12H2,1-3H3
InChIKey VLPIATFUUWWMKC-UHFFFAOYSA-N
SMILES CC(N)COc1c(C)cccc1C
Roles Classification
Application(s): 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.
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ChEBI Ontology
Outgoing mexiletine (CHEBI:6916) has role anti-arrhythmia drug (CHEBI:38070)
mexiletine (CHEBI:6916) is a aromatic ether (CHEBI:35618)
mexiletine (CHEBI:6916) is a primary amino compound (CHEBI:50994)
Incoming mexiletine hydrochloride (CHEBI:6917) has part mexiletine (CHEBI:6916)
IUPAC Name
1-(2,6-dimethylphenoxy)propan-2-amine
INNs Sources
mexiletina ChemIDplus
mexiletine ChemIDplus
mexiletinum ChemIDplus
Synonyms Sources
(±)-1-(2,6-dimethylphenoxy)propan-2-amine ChEBI
(2RS)-1-(2,6-dimethylphenoxy)-2-aminopropane ChEBI
1-(2',6'-dimethylphenoxy)-2-aminopropane NIST Chemistry WebBook
1-(2,6-dimethylphenoxy)-2-propanamine NIST Chemistry WebBook
1-methyl-2-(2,6-xylyloxy)ethanamine NIST Chemistry WebBook
Mexiletine KEGG COMPOUND
Database Links Databases
1794 DrugCentral
C07220 KEGG COMPOUND
D08215 KEGG DRUG
DB00379 DrugBank
FR1551055 Patent
HMDB14523 HMDB
LSM-1700 LINCS
Mexiletine Wikipedia
US3954872 Patent
View more database links
Registry Numbers Types Sources
2092205 Reaxys Registry Number Reaxys
31828-71-4 CAS Registry Number KEGG COMPOUND
31828-71-4 CAS Registry Number ChemIDplus
31828-71-4 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
10883344 PubMed citation Europe PMC
11009230 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comments
2014-07-10 Mexiletine can be found in blood and urine samples of individuals who have taken this drug.
2011-01-11 A class Ib anti-arrhythmic, mexiletine has actions similar to those of lidocaine, to which it is structurally related, but is orally active. Administered as the hydrochloride salt, it is used for the treatment of ventricular arrhythmias. It has a narrow therapeutic ratio; many adverse effects are dose-related and respond to dose reduction.