Quinine (CED0001330)

Record Information
Version1.0
Creation Date2009-07-21 20:26:58 UTC
Update Date2026-05-14 16:39:44 UTC
Accession NumberCHEM002202
Identification
Common NameQuinine
ClassSmall Molecule
Description
Quinine belongs to the cinchona alkaloids, a class of alkaloids and derivatives within the organic compounds. It has the formula C20H24N2O2 and an average molecular weight of 324.42 g/mol. This exogenous compound is a solid at room temperature. It is categorized as a drug (PMC8778081) and a biological alkaloid (PMC10369409). Quinine is used as an antimalarial (PMC7833388), a non-narcotic analgesic, and a muscle relaxant. Its industrial applications include use as a deodorizer and as a softener and conditioner. In terms of health effects, it is used in the treatment of malaria (PMC11943490, PMC13294913, PMC1492602, PMC7833388) and leishmaniasis (PMC11943490). The compound's protein targets include Hemoglobin subunit alpha (HBA1), Platelet glycoprotein IX (GP9), and Intermediate conductance calcium-activated potassium channel protein 4 (KCNN4). The theorized mechanism of action for quinine is that it is toxic to the malaria parasite by interfering with the parasite's ability to break down and digest hemoglobin, which causes the parasite to starve or build up toxic levels of partially degraded hemoglobin. Quinine is found in 22 recorded sources, including healthcare, pharmaceuticals and veterinary products such as antiprotozoals and drugs for disorders of the musculo-skeletal system. Other sources include food and food processing items like the preparation of wine or sparkling wine, vinegar, malt, wort, and molasses; household cleaning and consumer products such as tobacco pipes and non-electric simulated smoking devices; building and construction materials such as floors; and electrical and electronic equipment including magnets, relays, antennas, and electric hearing aids. The recorded exposure route for quinine is oral.
Contaminant Type
  • Amine
  • Analgesic, Non-Narcotic
  • Antimalarial
  • Drug
  • Ether
  • Food Toxin
  • Metabolite
  • Muscle Relaxant, Central
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Synonyms
ValueSource
(-)-QuinineChEBI
(8S,9R)-QuinineChEBI
(R)-(-)-QuinineChEBI
(R)-(6-Methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanolChEBI
6'-MethoxycinchonidineChEBI
ChininChEBI
ChinineChEBI
ChininumChEBI
QuininaChEBI
MyoquinMeSH
SurquinaMeSH
BiquinateMeSH
QuinimaxMeSH
Quinine bisulfateMeSH
Quinine sulfateMeSH
QuinoctalMeSH
QuinsonMeSH
QuinsulMeSH
Bisulfate, quinineMeSH
Hydrochloride, quinineMeSH
LegatrimMeSH
QuinammMeSH
QuinbisanMeSH
QuinbisulMeSH
Quinine lafranMeSH
Quinine sulphateMeSH
Quinine-odanMeSH
Sulfate, quinineMeSH
Sulphate, quinineMeSH
QuindanMeSH
Quinine hydrochlorideMeSH
StremaMeSH
6'-MethoxycinchonineHMDB
Quinine, anhydrousHMDB
QuinineanhydrousHMDB
Quinoline alkaloidHMDB
Aventis brand OF quinine bisulfateMeSH, HMDB
Fawns and mcallan brand OF quinine sulfateMeSH, HMDB
Foy brand OF quinine sulfateMeSH, HMDB
Plough brand OF quinine sulfateMeSH, HMDB
Fawns and mcallan brand OF quinine bisulfateMeSH, HMDB
Hoechst brand OF quinine sulfateMeSH, HMDB
Lafran brand OF quinine hydrochlorideMeSH, HMDB
Alphapharm brand OF quinine sulfateMeSH, HMDB
Innotech brand OF quinine hydrochlorideMeSH, HMDB
Odan brand OF quinine sulfateMeSH, HMDB
Prosana brand OF quinine bisulfateMeSH, HMDB
Chemical FormulaC20H24N2O2
Average Molecular Mass324.417 g/mol
Monoisotopic Mass324.184 g/mol
CAS Registry Number130-95-0
IUPAC Name(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
Traditional Namequinine
SMILES[H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12
InChI IdentifierInChI=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
InChI KeyLOUPRKONTZGTKE-WZBLMQSHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCinchona alkaloids
Sub ClassNot Available
Direct ParentCinchona alkaloids
Alternative Parents
Substituents
  • Cinchonan-skeleton
  • 4-quinolinemethanol
  • Quinoline
  • Anisole
  • Quinuclidine
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • 1,2-aminoalcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Organic oxygen compound
  • Aromatic alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Applications
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point57°C
Boiling PointNot Available
Solubility500 mg/L (at 15°C)
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP2.82ALOGPS
logP2.51ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)13.89ChemAxon
pKa (Strongest Basic)9.05ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.59 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.69 m³·mol⁻¹ChemAxon
Polarizability35.96 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4r-1901000000-8176add5a84f7ae1eb69Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05g0-7947000000-ee233460f7e7fbb00ca7Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ai-7930000000-eb63f68d11153566b027Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00c0-7910000000-c0d16dda8d8a74dd1657Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0059-5945000000-dff1a74853685996f965Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0009000000-4cf6c66b2059468cd1e3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0009000000-d4367d77a81731ba3654Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ai-7930000000-94e16a407d113a547240Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0059-5945000000-ddc4f19918fbae8ffe0cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fc0-6900000000-8bb456f41e7cb82dfcf9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fc0-6900000000-f458cccf839df1d5239bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00c0-7910000000-4b620f5ca762298602e7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-0019000000-0f42379f2989cf204f72Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-0729000000-5a0d8aa890e6c737bf45Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0079-0920000000-70e4fed1a61c38cf53fbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0109000000-e84ce15e838ff8ac33f6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-0229000000-b87ca7a53d952af7505eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0540-0920000000-12d8977ce43e168f8453Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0009000000-2125f5c1412244f91fb3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0109000000-1096d980c779fca1eb3fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dr-0920000000-468db2e8e8941541468cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0019000000-9c5f7ffbd0d69038e6daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0abi-0914000000-92707d10764c62ebe320Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0900000000-9e1ce60a980eb9551f33Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityThe theorized mechanism of action for quinine and related anti-malarial drugs is that these drugs are toxic to the malaria parasite. Specifically, the drugs interfere with the parasite's ability to break down and digest hemoglobin. Consequently, the parasite starves and/or builds up toxic levels of partially degraded hemoglobin in itself.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsFever, rarely hypotension. [wikipedia]
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
230.0Log mg/kg[130:410]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
malariais_treatment_forNot AvailablePMC11943490 , PMC13294913 , PMC1492602 , PMC7833388
leishmaniasisis_treatment_forNot AvailablePMC11943490
Exposure Sources
Source IDSourceSectorReference
368Drugs for disorders of the musculo-skeletal systemHealthcare, pharmaceuticals & veterinary productsNot Available
385AntiprotozoalsHealthcare, pharmaceuticals & veterinary productsNot Available
497FloorsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
534Still Video CamerasElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
601Lawn MowersAgriculture & land managementNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
621Chutes And SlidesRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
648Nitro DyesTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureCytochrome P450 2D4Q64680Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureA-type voltage-gated potassium channel KCND2Q63881Rattus norvegicusPredicted (SEA)0.0778492
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)12.378
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P08183HumansPredicted (SEA)3.34752
Click to view 3D structureCytochrome P450 2D26P10634Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureSolute carrier family 22 member 1Q63089Rattus norvegicusPredicted (SEA)0.0778492
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)190.108
Cholinesterase structureClick to view 3D structureCholinesteraseP06276HumansPredicted (SEA)37.4455
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)50.2906
Click to view 3D structureSolute carrier family 22 member 2O70577Mus musculusPredicted (SEA)0.0778492
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CP22002Rattus norvegicusPredicted (SEA)2.95827
Click to view 3D structureATP-dependent translocase ABCB1P06795Mus musculusPredicted (SEA)2.49118
Sodium channel protein type 5 subunit alpha structureClick to view 3D structureSodium channel protein type 5 subunit alphaQ14524HumansPredicted (SEA)90.3829
Solute carrier family 22 member 2 structureClick to view 3D structureSolute carrier family 22 member 2O15244HumansPredicted (SEA)0.544945
Click to view 3D structurePotassium voltage-gated channel subfamily A member 5P22460HumansPredicted (SEA)2.95827
Click to view 3D structureSolute carrier organic anion transporter family member 1A1P46720Rattus norvegicusPredicted (SEA)7.94062
Click to view 3D structureSolute carrier organic anion transporter family member 1A4O35913Rattus norvegicusPredicted (SEA)0.233548
Click to view 3D structureKappa-type opioid receptorQ2KIP6Bos taurusPredicted (SEA)3.89246
Click to view 3D structureSigma intracellular receptor 2Q3MHW7Bos taurusPredicted (SEA)3.89246
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)2935.85
Cyclin-G-associated kinase structureClick to view 3D structureCyclin-G-associated kinaseO14976HumansPredicted (SEA)761.21
Receptor-interacting serine/threonine-protein kinase 2 structureClick to view 3D structureReceptor-interacting serine/threonine-protein kinase 2O43353HumansPredicted (SEA)790.092
Aurora kinase A structureClick to view 3D structureAurora kinase AO14965HumansPredicted (SEA)2660.81
Click to view 3D structureSerine/threonine-protein kinase NLKQ9UBE8HumansPredicted (SEA)601.697
Atypical kinase COQ8A, mitochondrial structureClick to view 3D structureAtypical kinase COQ8A, mitochondrialQ8NI60HumansPredicted (SEA)464.916
Hemoglobin subunit alpha structureClick to view 3D structureHemoglobin subunit alphaP69905HumansKnownThe theorized mechanism of action for quinine and related anti-malarial drugs is that these drugs are toxic to the malaria parasite. Specifically, the drugs interfere with the parasite's ability to break down and digest hemoglobin. Consequently, the parasite starves and/or builds up toxic levels of partially degraded hemoglobin in itself.
Intermediate conductance calcium-activated potassium channel protein 4 structureClick to view 3D structureIntermediate conductance calcium-activated potassium channel protein 4O15554HumansKnownThe theorized mechanism of action for quinine and related anti-malarial drugs is that these drugs are toxic to the malaria parasite. Specifically, the drugs interfere with the parasite's ability to break down and digest hemoglobin. Consequently, the parasite starves and/or builds up toxic levels of partially degraded hemoglobin in itself.
Platelet glycoprotein IX structureClick to view 3D structurePlatelet glycoprotein IXP14770HumansKnownThe theorized mechanism of action for quinine and related anti-malarial drugs is that these drugs are toxic to the malaria parasite. Specifically, the drugs interfere with the parasite's ability to break down and digest hemoglobin. Consequently, the parasite starves and/or builds up toxic levels of partially degraded hemoglobin in itself.
Concentrations
Not Available
External Links
DrugBank IDDB00468
HMDB IDHMDB0014611
FooDB IDFDB002087
Phenol Explorer IDNot Available
KNApSAcK IDC00002193
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkQuinine
Chemspider ID84989
ChEBI ID15854
PubChem Compound ID3034034
Kegg Compound IDC06526
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Tong Sun, Shawn Watson, Wei Lai, Stephan D. Parent, “QUININE SULFATE/BISULFATE SOLID COMPLEX; METHODS OF MAKING; AND METHODS OF USE THEREOF.” U.S. Patent US20090326005, issued December 31, 2009.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10821711
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10891117
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=10937718
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11212126
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11549443
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=11728183
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=11844668
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=11855978
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=12127529
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=12213073
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=12217353
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=12477351
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=12502361
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=12798326
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=12873511
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=14761192
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=15026051
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=15027870
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=15225721
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=15857133
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=16524728
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=16933872
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=17482816
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=17506538
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=17570664
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=17850126
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=18348514
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=18788725
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=2579237
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=2657065
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=7009867
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=8182707
33. Paintaud G, Alvan G, Berninger E, Gustafsson LL, Idrizbegovic E, Karlsson KK, Wakelkamp M: The concentration-effect relationship of quinine-induced hearing impairment. Clin Pharmacol Ther. 1994 Mar;55(3):317-23.