CHEBI:8404 - prilocaine

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ChEBI Name prilocaine
ChEBI ID CHEBI:8404
Definition An amino acid amide in which N-propyl-DL-alanine and 2-methylaniline have combined to form the amide bond; used as a local anaesthetic.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:308749
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Formula C13H20N2O
Net Charge 0
Average Mass 220.31070
Monoisotopic Mass 220.158
InChI InChI=1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16)
InChIKey MVFGUOIZUNYYSO-UHFFFAOYSA-N
SMILES CCCNC(C)C(=O)Nc1ccccc1C
Roles Classification
Application(s): anticonvulsant
A drug used to prevent seizures or reduce their severity.
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.
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ChEBI Ontology
Outgoing prilocaine (CHEBI:8404) has role anticonvulsant (CHEBI:35623)
prilocaine (CHEBI:8404) has role local anaesthetic (CHEBI:36333)
prilocaine (CHEBI:8404) is a amino acid amide (CHEBI:22475)
prilocaine (CHEBI:8404) is a monocarboxylic acid amide (CHEBI:29347)
Incoming prilocaine hydrochloride (CHEBI:32053) has part prilocaine (CHEBI:8404)
IUPAC Name
N-(2-methylphenyl)-N2-propylalaninamide
INNs Sources
prilocaina ChemIDplus
prilocainum ChemIDplus
Synonyms Sources
2-(Propylamino)-o-propionotoluidide ChemIDplus
2-Methyl-alpha-propylaminopropionanilide ChemIDplus
alpha-n-Propylamino-2-methylpropionanilide ChemIDplus
N-(2-Methylphenyl)-2-(propylamino)propanamide ChemIDplus
o-Methyl-2-propylaminopropionanilide ChemIDplus
o-Methyl-alpha-propylaminopropionanilide ChemIDplus
prilocaine base ChEBI
Propitocaine ChemIDplus
Manual Xrefs Databases
2265 DrugCentral
C07531 KEGG COMPOUND
D00553 KEGG DRUG
DB00750 DrugBank
GB839943 Patent
LSM-5078 LINCS
Prilocaine Wikipedia
US3160662 Patent
View more database links
Registry Numbers Types Sources
2108498 Beilstein Registry Number Beilstein
721-50-6 CAS Registry Number ChemIDplus
721-50-6 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
26049614 PubMed citation Europe PMC
26199764 PubMed citation Europe PMC
26356490 PubMed citation Europe PMC
9989796 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2010-12-09 Prilocaine has similar anaesthetic potency to lidocaine, but is less toxic. It has a slower onset of action but a slightly longer duration of activity and less vasodilatory activity than lidocaine. A eutectic mixture of prilocaine and lidocaine is used topically for surface anaesthesia of the skin. Prilocaine hydrochloride is used particularly for infiltration anaesthesia in dentistry.