Description
Quinine is an alkaloid derived from the bark of the cinchona tree, acts as an anti-malaria agent. Quinine is a potassium channel inhibitor that inhibits WT mouse Slo3 (KCa5.1) channel currents evoked by voltage pulses to +100 mV with an IC50 of 169 μM.
Synonyms
(R)-[(2S,4S,5R)-1-Aza-5-vinylbicyclo[2.2.2]oct-2-yl](6-methoxyquinolin-4-yl)methanol
IUPAC Name
(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Molecular Formula
C20H24N2O2
Canonical 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
InChI Key
LOUPRKONTZGTKE-WZBLMQSHSA-N
Melting Point
173-175 °C (lit.)
Solubility
In water, 500 mg/L at 15 deg C;1 g dissolves in: 1900 mL water, 760 mL boiling water;1 g dissolves in: 80 mL benzene (18 mL at 50 deg C), 1.2 mL chloroform, 250 mL dry ether, 20 mL glycerol, 0.8 mL alcohol, 1900 mL of 10% ammonia water; almost insoluble in petroleum ether;Soluble in ether, chloroform, carbon disulfide, glycerol, alkalies, and acids (with formation of salts);Sol in pyrimidine;3.34e-01 g/L;
Application
Quinine occurs in the dried stems or rootbarks of cinchona (Cinchona ledgerianaMoens). It is used in the treatment of malaria.It is also used as an analgesic and antipyreticagent.A quinolinemethanol from the bark of the Cinchona tree; the laevorotatory stereoisomer of quinidine. Formulated as the sulfate, bisulfate or ethylcarbonate for oral use and as the dihydrochloride for parenteral administration. The salts are highly soluble in water.Falciparum malaria (alone or in combination with tetracycline, doxycycline, clindamycin or pyrimethamine-sulfadoxine) Babesiosis (in combination with clindamycin) It is particularly used in cerebral malaria if chloroquine resistance is suspected (Ch. 62). It is not recommended for treatment of uncomplicated falciparum malaria.
Storage
Keep in dark place. Inert atmosphere. Room temperature.
Color/Form
Triboluminescent, orthorhombic needles from absolute alcohol;Bulky, white, amorphous powder or crystalline alkaloid;CRYSTALS TURN BROWN ON EXPOSURE TO AIR;
Covalently-Bonded Unit Count
1
Decomposition
When heated to decomposition it emits toxic fumes of /nitrogen oxides/.;
Defined Atom Stereocenter Count
4
Hydrogen Bond Acceptor Count
4
Hydrogen Bond Donor Count
1
Isomeric SMILES
COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O
Monoisotopic Mass
324.183778013
Octanol Water Partition Coefficient
3.44 (LogP);log Kow = 3.44;2.6;
Other Experimental
Sublimes in high vacuum at 170-180 deg C blue fluorescence is especially strong in dilute sulfuric acid;MAX ABSORPTION (WATER): 347.5 NM (LOG E= 3.74) /HYDRATE/;Quinine sulfate occurs as fine, needle-like, white crystals which are usually lusterless and make a light and readily compressible mass; the drug has a persistent, very bitter taste. Quinine sulfate has solubilities of approximately 2 mg/mL in water and 8.3 mg/mL in alcohol at 25 deg C. /Quinine sulfate/;Microcrystalline powder; mp: 57 deg C; efflorescent; loses one water molecule in air, two water molecules over sulfuric acid; anhydrous at 125 deg C /Quinine trihydrate/;Very bitter crystals or crystalline powder; efflorescent on exposure to air and darkens on exposure to light. One gram dissolves in 9 mL water, 0.7 mL boiling water, 23 mL alcohol, 0.7 mL alcohol at 60 deg C, 625 mL chloroform, 2500 mL ether, 15 mL glycerol; pH: 3.5 /Bisulfate heptahydrate/;Bitter, silky needles. Effloresces on expsoure to warm air. Does not lose all its water below 120 deg C. One gram dissolves in 16 mL water, in 0.5 mL boiling water, in 1.0 mL alcohol, in about 7.0 mL glycerol, in about 1 ml chloroform, in about 350 mL ether. pH (1% aqueous solution): 6.0-7.0. Bitterness threshold 1:30000 /Quinine hydrochloride dihydrate/;Dull needles or rods, making a light and readily compressible mass. Becomes brownish on exposure to light. Loses its water of crystalization at about 100 deg C. Specific optical rotation: -220 deg at 16 deg C/D (5% solution in about 0.5N HCl). One gram dissolves in 810 mL water, 32 mL boiling water, 120 mL alcohol, 10 mL alcohol at 78 deg C. Slightly soluble in chloroform, ether but freely soluble in a mixture of 2 volumes chloroform and 1 volume absolute alcohol. Aqueous solutions are neutral to litmus, pH of saturated solution 6.2 /Quinine sulfate dihydrate/;Henry's Law constant = 8.58X10-16 atm-cu m/mol at 25 deg C (est);Hydroxl radical reaction rate constant = 1.60X10-10 cu cm/molec sec at 25 deg C (est);Ozone radical reaction rate constant = 1.20X10-17 cu cm/molec sec at 25 deg C (est);
pH
9.0 (0.5g/l, H2O, 20°C)
Physical Description
Solid;
Refractive Index
1.625 (15°C)
Shipping
Can be shipped at room temperature, where not in use may vary.
Source
PlantsRubiaceaeCinchona succirubra Pav. ex Klotzsch
Stability
Stable under normal temperatures and pressures. May discolor on exposure to light.
Storage Conditions
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store below 40°C.
Topological Polar Surface Area
45.6 Ų
Vapor Pressure
1.54X10-10 mm Hg at 25 deg C (est);
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