quinine

Also known as GNF-Pf-506, (R)-(6-methoxy-quinolin-4-yl)-((2S,5S)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol, (-)-quinine, (8S,9R)-quinine, (R)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol, chinine, 6'-methoxycinchonidine, (R)-(-)-quinine

Quinine is a medication used to treat malaria and babesiosis. This includes the treatment of malaria due to Plasmodium falciparum that is resistant to chloroquine when artesunate is not available. While sometimes used for nocturnal leg cramps, quinine is not recommended for this purpose due to the risk of serious side effects. It can be taken by mouth or intravenously. Malaria resistance to quinine occurs in certain areas of the world. Quinine is also used as an ingredient in tonic water and other beverages to impart a bitter taste.

OverviewAI-generated

Quinine is a chemical compound with the formula C₂₀H₂₄N₂O₂. Its IUPAC name is (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol. The substance has a mass of 324.184 and a weight of 324.4. It melts at 177 degrees. The median lethal dose (LD50) is 1.8.

Chemical properties include an xlogp of 2.9 and a tpsa of 45.6. The molecule contains one hydrogen bond donor and four hydrogen bond acceptors, with a charge of 0. The stylized name for the compound is quiNINE.

Quinine is referenced by 943 other encyclopedia articles. A search for quinine in PubMed yields 12445 results.

Synthesized by Vinony from 21 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 441980057
Drug.image: Quinine.svg
Drug.image_class: skin-invert-image
Drug.width: 200
Drug.image2: Quinine-3D-balls.png
Drug.image_class2: bg-transparent
Drug.width2: 180
Drug.pronounce: , or
Drug.tradename: Qualaquin, Quinbisul, others
Drug.MedlinePlus: a682322
Drug.DailyMedID: Quinine
Drug.licence_US: Quinine
Drug.pregnancy_AU: D
Drug.pregnancy_US: N
Drug.legal_AU: S4
Drug.legal_CA: Rx-only

via Wikipedia infobox

Chemical data

Formula: C20H24N2O2
Molecular weight: 324.4 g/mol
IUPAC name: (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
SMILES: COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O
InChIKey: LOUPRKONTZGTKE-WZBLMQSHSA-N
XLogP: 2.9
Polar surface area: 45.6 Å²
H-bond donors: 1
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

12,445 papers

Quinine toxicity.ReviewAdverse drug reactions and acute poisoning reviews · 1986Bateman DN, Dyson EH
Analytics of Quinine and its Derivatives.ReviewCritical reviews in analytical chemistry · 2016Kluska M, Marciniuk-Kluska A, Prukała D et al.DOI: 10.1080/10408347.2014.996700
Quinine for muscle cramps.The Cochrane database of systematic reviews · 2015El-Tawil S, Al Musa T, Valli H et al.DOI: 10.1002/14651858.CD005044.pub3
Quinine, an old anti-malarial drug in a modern world: role in the treatment of malaria.ReviewMalaria journal · 2011Achan J, Talisuna AO, Erhart A et al.DOI: 10.1186/1475-2875-10-144
Quinine.The Indian medical gazette · 1946CHAUDHURI RN
Cinchona bark and quinine as psychiatric treatments in Portugal, 1700-1900.ReviewDie Pharmazie · 2025Semedo MG, Pereira AL, Pita JRDOI: 10.1691/ph.2025.5015
Is quinine effective and safe in leg cramps?ReviewJournal of clinical pharmacology · 1995Mandal AK, Abernathy T, Nelluri SN et al.DOI: 10.1002/j.1552-4604.1995.tb05015.x
Quinine: the rediscovered anti-malarial agent.ReviewThe Central African journal of medicine · 1991Amabeoku GJ

via PubMed

Wikidata facts

Has part: hydrogen
Mass: 324.184
Has use: medication

Show 15 more facts

Commons category: Quinine
natural product of taxon: Cinchona
subject has role: antimalarial
chemical formula: C₂₀H₂₄N₂O₂
topic's main category: Category:Quinine
canonical SMILES: COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O
isomeric SMILES: COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O
significant drug interaction: mefloquine
has characteristic: bitterness
melting point: 177
different from: quinone
found in taxon: Ciliosemina pedunculata
legal status (medicine): boxed warning
stylized name: quiNINE
median lethal dose (LD50): 1.8

Sources (9)

via Wikidata · CC0

~20 min read

Encyclopedic overview

22 sections

Contents

Uses
Medical
Available forms
Beverages
Scientific
Contraindications
Adverse effects
Mechanism of action
Chemistry
Synthesis
Biosynthesis
Catalysis
History
Society and culture
Natural occurrence
{{anchor|Regulation in the US}} Regulation in the US
Abortion
Cutting agent
Other animals
References
Further reading
External links

Common side effects include headache, ringing in the ears, vision issues, and sweating. More severe side effects include deafness, low blood platelets, and an irregular heartbeat. Use can make one more prone to sunburn. While it is unclear if use during pregnancy carries potential for fetal harm, treating malaria during pregnancy with quinine when appropriate is still recommended. Quinine is an alkaloid, a naturally occurring chemical compound. It possesses a quinoline functional group (pyridine fused to benzene).

Excerpted from Wikipedia’s “quinine” article, available under the CC BY-SA 4.0 licence.