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.

AI overview

Quinine is a medication primarily used to treat malaria and babesiosis, particularly chloroquine-resistant malaria when other treatments aren't available, though it can also be taken by mouth or intravenously. Beyond medicine, quinine is added to beverages like tonic water for its bitter flavor, though its use for leg cramps is discouraged due to serious potential side effects, and resistance to it has developed in some parts of the world.

AI-generated from the Wikipedia summary — may 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

Mass: 324.184

Show 7 more facts

Commons category: Quinine
chemical formula: C₂₀H₂₄N₂O₂
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
melting point: 177
stylized name: quiNINE
median lethal dose (LD50): 1.8

Sources (9)

via Wikidata · CC0

~20 min read

Article

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).