CHEBI:6456 - lidocaine

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ChEBI Name lidocaine
ChEBI ID CHEBI:6456
Definition The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C14H22N2O
Net Charge 0
Average Mass 234.33736
Monoisotopic Mass 234.173
InChI InChI=1S/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)
InChIKey NNJVILVZKWQKPM-UHFFFAOYSA-N
SMILES CCN(CC)CC(=O)Nc1c(C)cccc1C
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): drug allergen
Any drug which causes the onset of an allergic reaction.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): drug allergen
Any drug which causes the onset of an allergic reaction.
local anaesthetic
Any member of a group of drugs that reversibly inhibit the propagation of signals along nerves. Wide variations in potency, stability, toxicity, water-solubility and duration of action determine the route used for administration, e.g. topical, intravenous, epidural or spinal block.
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 lidocaine (CHEBI:6456) has functional parent glycinamide (CHEBI:42843)
lidocaine (CHEBI:6456) has role anti-arrhythmia drug (CHEBI:38070)
lidocaine (CHEBI:6456) has role drug allergen (CHEBI:88188)
lidocaine (CHEBI:6456) has role environmental contaminant (CHEBI:78298)
lidocaine (CHEBI:6456) has role local anaesthetic (CHEBI:36333)
lidocaine (CHEBI:6456) has role xenobiotic (CHEBI:35703)
lidocaine (CHEBI:6456) is a benzenes (CHEBI:22712)
lidocaine (CHEBI:6456) is a monocarboxylic acid amide (CHEBI:29347)
lidocaine (CHEBI:6456) is a tertiary amino compound (CHEBI:50996)
Incoming lidocaine hydrochloride (CHEBI:50512) has part lidocaine (CHEBI:6456)
IUPAC Name
N-(2,6-dimethylphenyl)-N2,N2-diethylglycinamide
Synonyms Sources
2-(Diethylamino)-2',6'-acetoxylidide ChemIDplus
2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide ChemIDplus
α-diethylamino-2,6-dimethylacetanilide NIST Chemistry WebBook
Lidocaine KEGG DRUG
Brand Name Source
Lidoderm DrugBank
Database Links Databases
1579 DrugCentral
C07073 KEGG COMPOUND
D00358 KEGG DRUG
DB00281 DrugBank
GB706409 Patent
GB758224 Patent
HMDB0014426 HMDB
Lidocaine Wikipedia
LSM-3165 LINCS
US2441498 Patent
View more database links
Registry Numbers Types Sources
137-58-6 CAS Registry Number ChemIDplus
137-58-6 CAS Registry Number NIST Chemistry WebBook
2215784 Beilstein Registry Number Beilstein
2215784 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11106996 PubMed citation Europe PMC
11120381 PubMed citation Europe PMC
11431418 PubMed citation Europe PMC
11692349 PubMed citation Europe PMC
15056998 PubMed citation Europe PMC
16668583 PubMed citation Europe PMC
17214917 PubMed citation Europe PMC
18940244 PubMed citation Europe PMC
Last Modified
22 febrero 2017
General Comments
2010-12-10 Lidocaine is an amide-type local anaesthetic with a rapid onset of action, as well as an anti-arrhythmic, used in the treatment of ventricular arrhythmias, especially after myocardial infarction. It is generally used as the hydrochloride or the hydrochloride monohydrate.
2014-07-14 Lidocaine can be found in blood and urine samples of individuals who have taken this drug.
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag