Tmic
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Record Information
Version2.0
Creation Date2009-07-21 20:26:58 UTC
Update Date2014-12-24 20:25:51 UTC
Accession NumberT3D2800
Identification
Common NameQuinine
ClassSmall Molecule
DescriptionQuinine is an alkaloid derived from the bark of the cinchona tree. It is used as an antimalarial drug, and is the active ingredient in extracts of the cinchona that have been used for that purpose since before 1633. Quinine is also a mild antipyretic and analgesic and has been used in common cold preparations for that purpose. It was used commonly and as a bitter and flavoring agent, and is still useful for the treatment of babesiosis. Quinine is also useful in some muscular disorders, especially nocturnal leg cramps and myotonia congenita, because of its direct effects on muscle membrane and sodium channels. The mechanisms of its antimalarial effects are not well understood.
Compound Type
  • Amine
  • Analgesic, Non-Narcotic
  • Antimalarial
  • Drug
  • Ether
  • Food Toxin
  • Metabolite
  • Muscle Relaxant, Central
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
(-)-Quinine
(8S,9R)-Quinine
(R)-(-)-Quinine
(R)-(6-Methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol
6'-Methoxycinchonidine
6'-Methoxycinchonine
Chinin
Chinine
Chininum
Cinkona
Jasoquin
QSM
QUALAQUIN
Quinina
Quinine sulfate
Quinine sulphate
Quinine, Anhydrous
Quinineanhydrous
Quinlup
Quinoline Alkaloid
Qutil
Sulquin
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@@](O)(C1=C2C=C(OC)C=CC2=NC=C1)[C@]1([H])C[C@]2([H])CCN1C[C@]2([H])C=C
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 KeyInChIKey=LOUPRKONTZGTKE-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
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point57°C
Boiling PointNot Available
Solubility500 mg/L (at 15°C)
LogP3.44
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-1901000000-8176add5a84f7ae1eb69View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05g0-7947000000-ee233460f7e7fbb00ca7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0019000000-0f42379f2989cf204f72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0729000000-5a0d8aa890e6c737bf45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-0920000000-70e4fed1a61c38cf53fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0109000000-e84ce15e838ff8ac33f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-0229000000-b87ca7a53d952af7505eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0540-0920000000-12d8977ce43e168f8453View in MoNA
Toxicity Profile
Route of ExposureOral
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.
MetabolismHepatic, over 80% metabolized by the liver. Route of Elimination: Quinine is eliminated primarily via hepatic biotransformation. Approximately 20% of quinine is excreted unchanged in urine. Half Life: Approximately 18 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of malaria and leg cramps. Used as an antipyretic (fever-reducing), antimalarial, analgesic (painkilling), and anti-inflammatory. It is also used as a flavor component of tonic water and bitter lemon.
Minimum Risk LevelNot Available
Health EffectsIt is usual for quinine in therapeutic doses to cause cinchonism; in rare cases, it may even cause death (usually by pulmonary edema). Quinine can worsen hemoglobinuria, myasthenia gravis and optic neuritis. It can cause paralysis if accidentally injected into a nerve, and is extremely toxic in overdose[Wikipedia]
SymptomsFever, rarely hypotension. [wikipedia]
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00468
HMDB IDHMDB14611
PubChem Compound ID3034034
ChEMBL IDCHEMBL387326
ChemSpider ID84989
KEGG IDC06526
UniProt IDNot Available
OMIM ID
ChEBI ID15854
BioCyc ID3-HYDROXYQUININE
CTD IDNot Available
Stitch IDQuinine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkQuinine
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. 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. [8143397 ]
  2. Drugs.com [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBA1
Uniprot ID:
P69905
Molecular Weight:
15257.405 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
General Function:
Protein phosphatase binding
Specific Function:
Forms a voltage-independent potassium channel that is activated by intracellular calcium (PubMed:26148990). Activation is followed by membrane hyperpolarization which promotes calcium influx. Required for maximal calcium influx and proliferation during the reactivation of naive T-cells. The channel is blocked by clotrimazole and charybdotoxin but is insensitive to apamin (PubMed:17157250, PubMed:18796614).
Gene Name:
KCNN4
Uniprot ID:
O15554
Molecular Weight:
47695.12 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
General Function:
Not Available
Specific Function:
The GPIb-V-IX complex functions as the vWF receptor and mediates vWF-dependent platelet adhesion to blood vessels. The adhesion of platelets to injured vascular surfaces in the arterial circulation is a critical initiating event in hemostasis. GP-IX may provide for membrane insertion and orientation of GP-Ib.
Gene Name:
GP9
Uniprot ID:
P14770
Molecular Weight:
19045.87 Da
References
  1. Asvadi P, Ahmadi Z, Chong BH: Drug-induced thrombocytopenia: localization of the binding site of GPIX-specific quinine-dependent antibodies. Blood. 2003 Sep 1;102(5):1670-7. Epub 2003 May 8. [12738668 ]