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 Weight
324.42
Molecular Formula
C20H24N2O2
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
Boiling Point
462.75 °C
Melting Point
173-175 °C (lit.)
Flash Point
253.7°C
Purity
98%
Density
1.13 g/ml
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;
Appearance
Powder
Storage
Keep in dark place. Inert atmosphere. Room temperature.
Assay
0.9999
Color Form
Triboluminescent, orthorhombic needles from absolute alcohol;Bulky, white, amorphous powder or crystalline alkaloid;CRYSTALS TURN BROWN ON EXPOSURE TO AIR;
Complexity
457
Covalently-Bonded Unit Count
1
Decomposition
When heated to decomposition it emits toxic fumes of /nitrogen oxides/.;
Defined Atom Stereocenter Count
4
EC Number
205-003-2
Exact Mass
324.183778013
H-Bond Acceptor
4
H-Bond Donor
1
Heavy Atom Count
24
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
Odor
ODORLESS;
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);
Physical State
Solid
Refractive Index
1.625 (15°C)
Rotatable Bond Count
4
Stability
Stable under normal temperatures and pressures. May discolor on exposure to light.
Topological Polar Surface Area
45.6 Ų
UNII
A7V27PHC7A
Vapor Pressure
1.54X10-10 mm Hg at 25 deg C (est);
