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Various existing preparations include the hydrochloride , dihydrochloride, sulfate , bisulfate and gluconate. In the United States, quinine sulfate is commercially available in mg tablets under the brand name Qualaquin. All quinine salts may be given orally or intravenously IV ; quinine gluconate may also be given intramuscularly IM or rectally PR.
No injectable preparation of quinine is licensed in the US; quinidine is used instead. Quinine is a flavor component of tonic water and bitter lemon drink mixers. On the soda gun behind many bars, tonic water is designated by the letter "Q" representing quinine. According to tradition, the bitter taste of anti- malarial quinine tonic led British colonials in India to mix it with gin , thus creating the gin and tonic cocktail, which is still popular today. In Spain, quinine "Peruvian bark" is sometimes blended into sweet Malaga wine , which is then called "Malaga Quina".
In Italy, the traditional flavoured wine Barolo Chinato is infused with quinine and local herbs and is served as a digestif. In Canada and Italy, quinine is an ingredient in the carbonated chinotto beverages Brio and San Pellegrino. In Scotland, the company A. Barr uses quinine as an ingredient in the carbonated and caffeinated beverage Irn-Bru. In Denmark, it is used as an ingredient in the carbonated sports drink Faxe Kondi made by Royal Unibrew.
Quinine and quinidine are used as the chiral moiety for the ligands used in Sharpless asymmetric dihydroxylation as well as for numerous other chiral catalyst backbones. Because of its relatively constant and well-known fluorescence quantum yield , quinine is used in photochemistry as a common fluorescence standard. Because of the narrow difference between its therapeutic and toxic effects, quinine is a common cause of drug-induced disorders, including thrombocytopenia and thrombotic microangiopathy. Quinine can cause hemolysis in G6PD deficiency an inherited deficiency , but this risk is small and the physician should not hesitate to use quinine in people with G6PD deficiency when there is no alternative.
Some people who have developed TTP due to quinine have gone on to develop kidney failure. The most common adverse effects involve a group of symptoms called cinchonism , which can include headache, vasodilation and sweating, nausea, tinnitus , hearing impairment, vertigo or dizziness, blurred vision, and disturbance in color perception.
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Quinine ethyl carbonate is tasteless and odourless, [31] but is available commercially only in Japan. Blood glucose, electrolyte and cardiac monitoring are not necessary when quinine is given by mouth. Quinine is theorized to be toxic to the malarial pathogen, Plasmodium falciparum , by interfering with the parasite's ability to dissolve and metabolize hemoglobin.
This model involves the inhibition of hemozoin biocrystallization in Heme Detoxification pathway, which facilitates the aggregation of cytotoxic heme. Free cytotoxic heme accumulates in the parasites, causing their deaths. Cinchona trees remain the only economically practical source of quinine. However, under wartime pressure, research towards its synthetic production was undertaken. A formal chemical synthesis was accomplished in by American chemists R.
Woodward and W. The first synthetic organic dye , mauveine , was discovered by William Henry Perkin in while he was attempting to synthesize quinine. In the first step of quinine biosynthesis, the enzyme strictosidine synthase catalyzes a stereoselective Pictet—Spengler reaction between tryptamine and secologanin to yield strictosidine. Hydrolysis and decarboxylation would initially remove one carbon from the iridoid portion and produce corynantheal. Then the tryptamine side-chain were cleaved adjacent to the nitrogen, and this nitrogen was then bonded to the acetaldehyde function to yield cinchonaminal.
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Ring opening in the indole heterocyclic ring could generate new amine and keto functions. The new quinoline heterocycle would then be formed by combining this amine with the aldehyde produced in the tryptamine side-chain cleavage, giving cinchonidinone. For the last step, hydroxylation and methylation gives quinine. Quinine was used as a muscle relaxant by the Quechua , who are indigenous to Peru , Bolivia and Ecuador , to halt shivering due to low temperatures.
The Jesuit were the first to bring cinchona to Europe. A popular story of how it was brought to Europe by the Countess of Chinchon was debunked by medical historian Alec Haggis around Malaria was responsible for the deaths of several popes , many cardinals and countless common Roman citizens. Most of the priests trained in Rome had seen malaria victims and were familiar with the shivering brought on by the febrile phase of the disease. The Jesuit brother Agostino Salumbrino — , [47] an apothecary by training who lived in Lima , observed the Quechua using the bark of the cinchona tree for that purpose.
While its effect in treating malaria and malaria-induced shivering was unrelated to its effect in controlling shivering from rigors , it was a successful medicine against malaria. At the first opportunity, Salumbrino sent a small quantity to Rome for testing as a malaria treatment.
The form of quinine most effective in treating malaria was found by Charles Marie de La Condamine in Prior to , the bark was first dried, ground to a fine powder, and then mixed into a liquid commonly wine which was then drunk. Large-scale use of quinine as a malaria prophylaxis started around In Paul Briquet published a brief history and discussion of the literature on "quinquina".
Quinine played a significant role in the colonization of Africa by Europeans. Quinine had been said to be the prime reason Africa ceased to be known as the "white man's grave". A historian has stated, "it was quinine's efficacy that gave colonists fresh opportunities to swarm into the Gold Coast , Nigeria and other parts of west Africa". To maintain their monopoly on cinchona bark, Peru and surrounding countries began outlawing the export of cinchona seeds and saplings in the early 19th century.
The Dutch government persisted in its attempts to smuggle the seeds, and in the late 19th century the Dutch grew the plants in Indonesian plantations. Soon they became the main suppliers of the plant, and in they set up the Kina Bureau, a cartel of cinchona producers charged with controlling price and production. The US had obtained four million cinchona seeds from the Philippines and began operating cinchona plantations in Costa Rica.
Additionally, they began harvesting wild cinchona bark during the Cinchona Missions. Such supplies came too late.