Quinine

• CAS: 130-95-0
• Catalog Number: ACM130950
• Category: Inhibitors
• Molecular Weight: 324.42
• Molecular Formula: C20H24N2O2
• 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
• 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
• Boiling Point: 462.75 °C
• Melting Point: 173-175 °C (lit.)
• Flash Point: 253.7°C
• 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
• 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.
• Active Content: 95%
• 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
• 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
• 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)
• Packaging: 1 kg
• pH: 9.0 (0.5g/l, H2O, 20°C)
• Physical Description: Solid
• Physical State: Solid
• pKa: 8.52
• Refractive Index: 1.625 (15°C)
• Rotatable Bond Count: 4
• 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
• UNII: A7V27PHC7A
• Vapor Pressure: 1.54X10-10 mm Hg at 25 deg C (est)

Custom Q&A

What is the chemical formula of Quinine?

The chemical formula of Quinine is C20H24N2O2.

What is the primary pharmacological mechanism of action of Quinine?

Quinine is a potent schizontocidal agent against all human plasmodial species.

What are the indications for using Quinine?

Quinine is the drug of choice in the treatment of severe and complicated chloroquine-resistant P. falciparum malaria. It is also useful for the treatment of non-severe chloroquine-resistant cases.

What are the side effects commonly associated with Quinine?

The side effects commonly seen at therapeutic concentrations are known as cinchonism, which include ringing in the ears, impairment of hearing, headache, nausea, vertigo, vision changes, and more severe symptoms in acute intoxication.

What are the contraindications for using Quinine?

Quinine should be avoided in patients who are hypersensitive to the drug, as well as in patients with optic neuritis and myasthenia gravis, and those with certain cardiac conditions.

What interactions should be considered when administering Quinine?

Quinine can increase digoxin plasma levels and interact with cimetidine by reducing clearance. It also shares most of the drug interactions seen with quinidine.

What are the preparations of Quinine available for use?

Various preparations of Quinine salts are available, including hydrochloride, dihydrochloride, sulphate, and bisulphate salts.

What are the main uses of Quinine?

Quinine is used for the treatment of malaria caused by Plasmodium falciparum, and it can also be used in combination with other medications for malaria treatment.

What is the pharmacokinetics of Quinine?

Quinine undergoes rapid and complete oral absorption, reaching peak plasma concentration within 1 to 3 hours. It has a plasma protein binding rate of about 70% and a half-life of 7 to 8 hours.

What are some of the potential side effects of using Quinine?

Potential side effects of using Quinine include cinchona reaction, characterized by nausea, vomiting, tinnitus, headache, vision hearing loss, as well as specific reactions like acute hemolysis.