CHEBI:15854 - quinine

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ChEBI Name quinine
ChEBI ID CHEBI:15854
Definition A cinchona alkaloid that is cinchonidine in which the hydrogen at the 6-position of the quinoline ring is substituted by methoxy.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:15001, CHEBI:127176, CHEBI:355947, CHEBI:8723, CHEBI:602929, CHEBI:569215, CHEBI:26499
Supplier Information eMolecules:3322300, ZINC000003324905
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Formula C20H24N2O2
Net Charge 0
Average Mass 324.41680
Monoisotopic Mass 324.18378
InChI InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1
InChIKey LOUPRKONTZGTKE-WZBLMQSHSA-N
SMILES [H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)c1ccnc2ccc(OC)cc12
Roles Classification
Biological Role(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
muscle relaxant
A drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis.
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ChEBI Ontology
Outgoing quinine (CHEBI:15854) has parent hydride (8S)-cinchonan (CHEBI:59138)
quinine (CHEBI:15854) has role antimalarial (CHEBI:38068)
quinine (CHEBI:15854) has role muscle relaxant (CHEBI:51371)
quinine (CHEBI:15854) has role non-narcotic analgesic (CHEBI:35481)
quinine (CHEBI:15854) is a cinchona alkaloid (CHEBI:51323)
quinine (CHEBI:15854) is conjugate base of quinine(1+) (CHEBI:137041)
Incoming 3-hydroxyquinine (CHEBI:17685) has functional parent quinine (CHEBI:15854)
quinine sulfate (CHEBI:52250) has part quinine (CHEBI:15854)
quinine(1+) (CHEBI:137041) is conjugate acid of quinine (CHEBI:15854)
quininyl group (CHEBI:52903) is substituent group from quinine (CHEBI:15854)
IUPAC Name
(9R)-6'-methoxy-8α-cinchonan-9-ol
Synonyms Sources
(−)-quinine ChemIDplus
(-)-Quinine KEGG COMPOUND
(8S,9R)-quinine NIST Chemistry WebBook
(R)-(−)-quinine ChEBI
(R)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol ChEBI
6'-methoxycinchonidine ChEBI
Chinin ChemIDplus
chinine ChEBI
chininum ChEBI
quinina ChEBI
quinine ChEMBL
Quinine KEGG COMPOUND
Manual Xrefs Databases
4523 DrugCentral
C00002193 KNApSAcK
C06526 KEGG COMPOUND
D08460 KEGG DRUG
DB00468 DrugBank
Quinine Wikipedia
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Registry Numbers Types Sources
130-95-0 CAS Registry Number ChemIDplus
130-95-0 CAS Registry Number NIST Chemistry WebBook
91867 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017
General Comment
2011-03-18 Obtained from the bark of Cinchona species, quinine was the first effective anti-malarial. Other uses include treatment of certain muscular disorders, such as nocturnal leg cramps and congenital myotonia, and giving the characteristic bitter taste to tonic water.