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Quinine

CAT: 0013-GTR19163883-02Size: 1 gDry Ice: NoHazardous: No
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Description
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. (In Vitro) :Quinine (150 μM, 30 min) inhibits the proliferation and cytostatic effects of DENV (Dengue virus) in human hepatocarcinoma HepG2 cell line.Quinine (37.5-150 μM, 24 hours) significantly reduces viral DENV RNA and protein levels in a dose-dependent manner in human hepatocarcinoma HepG2 cell line. (In Vivo) :Quinine (oral gavage, 12 or 15 mg/kg, every week, 16 weeks) has some tumor suppressing effect on skin cancer in Swiss albino mice.Quinine (oral gavage, 10 mg/kg, everyday, 8 weeks) causes a decrease in the antioxidant defense system of rat testicular tissue such as SOD, CAT and GSH enzyme activity in male adult albino rats.
CAS Number
130-95-0
Product Name Alternative
NSC 192949
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
Soluble in Water
Smiles
COC1=CC2=C (C=CN=C2C=C1) C (C3CC4CCN3CC4C=C) O
Molecular Formula
C20H24N2O2
Molecular Weight
324.42
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
(R) -[ (2S,4S,5R) -5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]- (6-methoxyquinolin-4-yl) methanol

Chemical Information

Quinine

Quinine is a cinchona alkaloid that is cinchonidine in which the hydrogen at the 6-position of the quinoline ring is substituted by methoxy. It has a role as a non-narcotic analgesic, an antimalarial and a muscle relaxant. It is a conjugate base of a quinine(1+). It derives from a hydride of an (8S)-cinchonan.

CAS Number130-95-0
PubChem CID3034034
IUPAC Name(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Molecular FormulaC20H24N2O2
Molecular Weight324.4
XLogP2.9
Topological Polar Surface Area45.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Heavy Atom Count24
Formal Charge0
Complexity457
SMILES
COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O
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
Chemical Structure
2D Structure
2D structure of Quinine
CAS: 130-95-0
CID: 3034034
Formula: C20H24N2O2
MW: 324.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight324.4
XLogP32.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass324.183778013
Monoisotopic Mass324.183778013
Topological Polar Surface Area45.6 Ų
Heavy Atom Count24
Formal Charge0
Complexity457
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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