lidocaine (CHEBI:6456)

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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

Average Mass

234.33736

Monoisotopic Mass

234.17321

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. Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

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.

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

Last Modified

22 February 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