CHEBI:247956 - cinchocaine

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ChEBI Name cinchocaine
ChEBI ID CHEBI:247956
Definition A monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally only used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:4500
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Formula C20H29N3O2
Net Charge 0
Average Mass 343.46320
Monoisotopic Mass 343.22598
InChI InChI=1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)
InChIKey PUFQVTATUTYEAL-UHFFFAOYSA-N
SMILES CCCCOc1cc(C(=O)NCCN(CC)CC)c2ccccc2n1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Application(s): topical anaesthetic
A local anesthetic that is used to numb the surface of a body part.
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ChEBI Ontology
Outgoing cinchocaine (CHEBI:247956) has role topical anaesthetic (CHEBI:48425)
cinchocaine (CHEBI:247956) is a aromatic ether (CHEBI:35618)
cinchocaine (CHEBI:247956) is a monocarboxylic acid amide (CHEBI:29347)
cinchocaine (CHEBI:247956) is a tertiary amino compound (CHEBI:50996)
Incoming cinchocaine hydrochloride (CHEBI:59735) has part cinchocaine (CHEBI:247956)
IUPAC Name
2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
INNs Sources
cinchocaine ChEBI
cinchocainum ChemIDplus
cincocainio ChemIDplus
Synonyms Sources
2-butoxy-N-(2-(diethylamino)ethyl)cinchoninamide ChemIDplus
2-butoxy-N-(α-diethylaminoethyl)cinchoninamide ChemIDplus
2-butoxy-N-(β-diethylaminoethyl)cinchoninamide NIST Chemistry WebBook
2-butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide NIST Chemistry WebBook
2-Butoxy-quinoline-4-carboxylic acid (2-diethylamino-ethyl)-amide ChEMBL
2-butoxyquinoline-4-carboxylic acid diethylaminoethylamide ChemIDplus
2-N-butoxy-N-(2-diethylaminoethyl)cinchoninamide ChemIDplus
α-butyloxycinchonic acid-γ-diethylethylenediamine ChemIDplus
α-butyloxycinchoninic acid diethylethylenediamide NIST Chemistry WebBook
α-butyloxycinchoninic acid diethylethylenediamide ChemIDplus
CINCHOCAINE ChEMBL
Dibucaine KEGG COMPOUND
DIBUCAINE ChEMBL
dibucaine ChEMBL
dibucaine base ChemIDplus
N-(2-(diethylamino)ethyl)-2-butoxycinchoninamide ChemIDplus
Manual Xrefs Databases
859 DrugCentral
C07879 KEGG COMPOUND
D00733 KEGG DRUG
DB00527 DrugBank
Dibucaine Wikipedia
HMDB0014668 HMDB
LSM-6018 LINCS
US1825623 Patent
View more database links
Registry Numbers Types Sources
275489 Beilstein Registry Number Beilstein
275489 Reaxys Registry Number Reaxys
85-79-0 CAS Registry Number KEGG COMPOUND
85-79-0 CAS Registry Number NIST Chemistry WebBook
85-79-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
23953476 PubMed citation Europe PMC
2873227 PubMed citation Europe PMC
Last Modified
22 February 2017