Quinine

Catalog Number	ACM130950
CAS Number	130-95-0
Structure
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
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
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
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.
Complexity	457
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	4
EC Number	205-003-2
Exact Mass	324.183778013
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
PhysicalState	Solid
Rotatable Bond Count	4
Topological Polar Surface Area	45.6 Ų

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.

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