Quinine
| Quinine | |
|---|---|
 
| |
| General | |
| Systematic name | (R)-[(2S,4S,5R)-5-ethenyl- 1-azabicyclo [2.2.2]octan-2-yl]- (6-methoxyquinolin-4-yl)methanol |
| Other names | Qualaquin, Quinate, Quinbisul |
| Molecular formula | C20H24N2O2 |
| Molar mass | 324.417 g/mol |
| Appearance | Solid |
| CAS number | 130-95-0 |
| Properties | |
| Density and phase | [[1.21g/cm3]], Solid |
| Solubility in water | 1 g/1900 ml (25°C) |
| Melting point | Decomposes, 177°C |
| Hazards | |
| MSDS | Material safety data sheet |
| Main hazards | Irritant (skin contact), Hazardous in case of ingestion |
| NFPA 704 |
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| RTECS number | VA6020000 |
| Related compounds | |
| Related | Quindine, Epiquinine, Quinine Sulfate |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Disclaimer and references | |
Quinine is a compound that is sometimes used as an antmialarial drug. When used as a medication, however, it has many potential life-threatening side effects.[1] The chemical formula of quinine is C20H24N2O2 and it appears as a bulky white crystalline. [2] Quinine is also found in tonic water, a carbonated soft drink, and bitter lime and has a bittersweet taste to it. [1] The compound quinine can be extracted from the bark of the cinchona tree, now grown in areas it is not native to, for commercial reasons. [3] Quinine can also be used to treat leg cramps, but it is not FDA approved because of the severe adverse effects. [4]
Properties
Quinine is a bulky, natural white crystalline alkaloid that possesses anti-malarial with analgesic and anti-inflammatory properties.[5] The chemical formula of quinine is C20H24N2O2. The molecular weight of quinine is 324.41676 g/mol. [2] Quinine is also quite a fluorescent compound in a dilute acid solution with a fluorescence emission at 450 nm. [6] The compound quinine has no odor and has a very bitter taste to it. When this compound is heated, it decomposes and emits toxic fumes of nitrogen oxides. [2]
Natural Occurrences and Synthesis
Quinine is naturally gathered from the cinchona or the quinine bark. The bark of the tree is the main part that is used to produce the quinine.[4] The quinine bark was first advertised for sale in England in 1658 and was later more widely recognized because of its effectiveness with malaria. The natural bark of the cinchona is still currently employed in herbal medicine systems around the world. The Cinchona trees grow up to 15-20 meters in height and produce white, pink or yellow flower. These trees are native to the eastern slopes of the Amazonian area of the Andes and they could also be found north of the Andes. Nowadays these quinine producing trees are widely cultivated in other countries for commercial purposes. [3]
The process of the manufacturing of quinine involves the extraction from the bark. Afterwards it is treated carbonate or sodium hydroxide and then extracted into hot mineral oil. Then the compound is purified by re-crystallization. Finally the ground up bark of the cinchona is mixed with lime in hot oil. The resulting solution is then filtered and diluted with sulfuric acid. Then the rest is neutralized with hot sodium carbonate, and while cooling the quinine sulfate crystallizes out. Following this, the sulfate is treated with ammonia, then creating the alkaloid.[2]
Uses
Quinine has many various uses as a medication. Some include the treatment of malaria, leg cramps caused by vascular spasm, internal hemorrhoids, and varicose veins.[7] Quinine is a medication that is used to treat uncomplicated P. falciparum malaria, but no other type of malaria. It is not supposed to be taken to prevent malaria in general, but just to treat one specific type of malaria. [8] Like most medications, quinine can have potentially life-threatening adverse effects when taken. Some of these effects of quinine can cause cinchonism, hypoglycemia, serious hematologic disorders, urticaria, contact dermatitis, and other hypersensitivity reactions. [7] Another serious side effect of quinine includes a decrease in platelets. This is a condition called thrombocytopenia and it can eventually cause serious bleeding or kidney disease. [1]
The compound quinine is also found in tonic water and bitter lemon. The amount of quinine found in these beverages is quite small when compared to the amount in medications. It still is not recommended to drink large amounts of tonic water because of the effects quinine could have. However, if a pregnant woman were to drink a great amount of tonic water every day, the child would have quinine in their urine when born.[1]
History
Quinine was first discovered in the seventeenth century. However natives in South America also used quinine to treat malaria as early as the 1600's. [9] The name of the bark that quinine came from was called "Jesuits' bark". This name stems from the use by Jesuit missionaries in South America. There was also a legend of a native girl treated by the bark to heal her "fever". [10] The most effective form of treatment was found by Charles Marie de la COndamine in 1737. [11]
Video
Short video with a 3D model of quinine.
References
- ↑ 1.0 1.1 1.2 1.3 Perkins, Sharon. List of Foods That Contain Quinine Livestrong. Web. Last updated April 23, 2015.
- ↑ 2.0 2.1 2.2 2.3 Quinine Pub Chem. Web. Last updated January 11 2016 Unknown Author.
- ↑ 3.0 3.1 Taylor, Leslie. Quinine Tropical Plant Database. Web. Last updated December 28, 2012.
- ↑ 4.0 4.1 Bryner, Michelle. What Is Quinine? livescience. Web. Published April 14, 2014.
- ↑ Quinine Science of Cooking. Web. Last accessed January 13, 2016. Unknown Author
- ↑ Sawyer, Donald T.; Heineman, William R.; Beebe,Janice M. Characterization of Quinine and Its Determination Colby.edu. Web. Last accessed January 13, 2016.
- ↑ 7.0 7.1 Quinine Drugs.com. Web. Last accessed January 6, 2016. Unknown Author
- ↑ Coronado, Katie. Quinine (Qualaquin Everyday Health. Web. Latest Update: 10/28/2014
- ↑ Malar, J. Quinine, an old anti-malarial drug in a modern world: role in the treatment of malaria NCBI. Web. Publihed: May 24, 2011
- ↑ A SHORT HISTORY OF THE FEVER TREE Fever-Tree. Web. Last Accessed: January 29, 2016. Unknown Author
- ↑ Pletcher, Kenneth Charles-Marie de La Condamine Encyclopedia Britannica. Web. Last Accessed: January 29, 2016
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