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Quinine

Quinine

Quinine is an alkaloid found in the bark of the cinchona tree. Quinine has been used to treat malaria (a recurring disease marked by severe chills and fever) since the early 1600s. It was the best chemotherapeutic (chemical therapeutic) agent available to combat the disease until the 1920s. Malaria treatment by quinine marked the first successful use of a chemical compound to treat an infectious disease.

The Discovery of Quinine

Quinine has been referred to as "Jesuits' bark," "cardinal's bark," and "sacred bark." Its name stems from its use in 1630 by Jesuit missionaries in the Andes (a mountain range in western South America). A legend suggests earlier use by the native population. According to the legend, an Indian with a high fever was lost in an Andean jungle. When he drank from a pool of stagnant (standing) water, he found it tasted bitter. Realizing it had been contaminated by the surrounding quina-quina trees he thought he was poisoned. But his fever abated, and thereafter his village used extracts made from quina-quina bark to treat fevers.

The legend of quinine's discovery accepted in Europe involves the Countess of Chinchon, who had visited Peru. While in Peru the countess contracted a fever which was cured by the bark of a tree. Returning to Spain with the bark, she introduced quinine to Europe in 1638. In 1742 Swedish botanist Carol Linnaeus (1707-1778) called the tree "Cinchona" in her honor. The legend is a bit faulty. In fact, the Countess never had malaria and died in Colombia before reaching Spain.

Synthesizing Quinine

Malaria is a lethal disease worldwide. Because it is so widespread, the potential value of quinine inspired research into its synthesis. In 1820 French chemist Pierre-Joseph Pelletier (1788-1842) and Joseph-Bienaime Caventou (1795-1877) isolated quinine from cinchona bark. In 1908, P. Rabe theorized the correct chemical structure of quinine. This structure was not confirmed, however, until 1944 when American chemist Robert Burns Woodward (1917-1989; 1965 Nobel Prize winner in chemistry) and William von Eggers Doering first successfully synthesized the chemical. This was an amazing achievement of synthetic organic chemistry, but of little commercial value as the cost of the process was too high to be practical.

In the beginning of the twentieth century most of the naturally produced quinine originated in Java, now part of Indonesia. During World War I (1914-1918), Germany was cut off from supplies of quinine and developed the synthetic substitute Atabrine. By 1942 when the United States entered World War II (1939-1945), the Javanese plantations were controlled by Japan. American soldiers fighting in North Africa and the South Pacific islands were devastated by malaria. White pills taken from captured Italian soldiers were sent back to the United States. They were found to be the synthetic antimalarial drug chloroquine. The drug was manufactured by the same German lab as Atabrine. The United States was then able to synthesize several tons of its own before the end of the war.

Today, both chloroquine and Atabrine are used to prevent malaria. There are areas of the world, however, where malaria parasites have developed a resistance to synthetic drugs. Vietnam is one of those areas. For those cases, quinine is still effective in malaria treatment.

[See also Chemotherapy ]

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quinine

quinine (kwī´nīn´, kwĬnēn´), white crystalline alkaloid with a bitter taste. Before the development of more effective synthetic drugs such as quinacrine, chloroquine, and primaquine, quinine was the specific agent in the treatment of malaria. Almost insoluble in water, it dissolves readily in alcohol and other organic solvents. It is derived from the bark, called quina quina by the indigenous people of Peru, of several species of Cinchona and is used in the form of a salt, especially the sulfate. By the middle of the 17th cent. Jesuit missionaries had brought cinchona bark to Europe from South America, and quinine was isolated in 1820 by the French chemists J. B. Caventou and P. J. Pelletier; chemical synthesis was achieved in 1944 by R. B. Woodward and W. E. Doering, American chemists.

Certain strains of the malarial parasite Plasmodium falciparum have now developed a resistance to chloroquine, and quinine is again the preferred drug in some regions. Quinine also has been used medicinally to allay fever and pain, to induce uterine contractions during labor, and as a sclerosing, or hardening, agent in the treatment of varicose veins. It is added to soft drinks called tonics, which are often mixed with alcoholic beverages. Excessive dosage or continuous use of quinine may cause cinchonism, characterized by ringing in the ears, headache, dizziness, changes in blood pressure, and even death.

See F. Rocco, The Miraculous Fever-Tree (2003).

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quinine

quinine (kwin-een) n. a drug used in the treatment of malaria due to Plasmodium falciparum. Small doses of quinine are used to treat nocturnal leg cramps. It is administered by mouth or injection; large doses can cause severe poisoning (see cinchonism).

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quinine

quinine White, crystalline substance isolated in 1820 from the bark of the cinchona tree. It was once widely used in the treatment of malaria but has been largely replaced by drugs that are less toxic and more effective.

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quinine

qui·nine / ˈkwīˌnīn/ • n. a bitter crystalline compound, C20H24N2O2, present in cinchona bark, used as a tonic and formerly as an antimalarial drug.

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quinine

quinine Bitter alkaloid extracted from the bark of the cinchona tree (Cinchona officinalis), used to treat or prevent malaria and in aperitif wines, bitters, and tonic water.

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quinine

quinine XIX. f. quina bark of cinchona, etc. — Sp. — Quechua kina bark; see -INE3.

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quinine

quinine •gamine • bromine • thiamine •dopamine • amphetamine • histamine •quinine • strychnine • mezzanine •spalpeen • Philippine • lycopene •gangrene • terrene • silkscreen •windscreen • citrine • Dexedrine •putting green • Benzedrine •Irene, polystyrene •widescreen • sight screen •chlorine, chorine, Doreen, Maureen, Noreen, taurine •smokescreen • rood screen •sunscreen • fluorine • helleborine •Gadarene • Hippocrene •glycerine (US glycerin), nitroglycerine (US nitroglycerin) •nectarine • wintergreen • Methedrine •evergreen • wolverine • vaccine •glassine • Essene • Rexine • piscine •epicene • glycine • pyroxene •Palaeocene (US Paleocene) •Pliocene • Miocene • Holocene •damascene • kerosene • Plasticine •Pleistocene

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Quinine

Quinine

History

Uses and manufacture

Resources

Quinine is an alkaloid obtained from the bark of several species of the cinchona tree. Until the development of synthetic drugs, quinine was used as the primary treatment of malaria, a disease that kills over 100 million people a year. The cinchona tree is native to the eastern slopes of the Andes Mountains in South America. Today, the tree is cultivated throughout Central and South America, Indonesia, India, and some areas in Africa. The cinchona tree contains more than 20 alkaloids of which quinine and quinidine are the most important. Quinidine is used to treat cardiac arrhythmias.

History

South American Indians have been using cinchona bark to treat fevers for many centuries. Spanish conquerors learned of quinines medicinal uses in Peru, at the beginning of the seventeenth century. Use of the powdered Peruvian bark was first recorded in religious writings by the Jesuits in 1633. The Jesuit fathers were the primary exporters and importers of quinine during this time and the bark became known as Jesuit bark. The cinchona tree was named for the wife of the Spanish viceroy to Peru, Countess Anna del Chinchon. A popular story is that the Countess was cured of the ague (a name for malaria the time) in 1638. The use of quinine for fevers was included in medical literature in 1643. Quinine did not gain wide acceptance in the medical community until Charles II was cured of the ague by a London apothecary at the end of the seventeenth century. Quinine was officially recognized in an edition of the London Pharmacopoeia as Cortex Peruanus in 1677. Thus began the quest for quinine. In 1735, Joseph de Jussieu, a French botanist, accompanied the first non-Spanish expedition to South America and collected detailed information about the cinchona trees. Unfortunately, as Jussieu was preparing to return to France, after 30 years of research, someone stole all his work. Charles Marie de la Condamine, leader of Jussieus expedition, tried unsuccessfully to transfer seedlings to Europe. Information about the cinchona tree and its medicinal bark was slow to reach Europe. Scientific studies about quinine were first published by Alexander von Humboldt and Aime Bonpland in the first part of the 18th century. The quinine alkaloid was separated from the powdered bark and named quinine in 1820 by two French doctors. The name quinine comes from the Amerindian word for the cinchona tree, quinaquina, which means bark of barks. As European countries continued extensive colonization in Africa, India, and South America, the need for quinine was great, because of malaria. The Dutch and British cultivated cinchona trees in their East Indian colonies but the quinine content was very low in those species. A British collector, Charles Ledger, obtained some seeds of a relatively potent Bolivian species, Cinchona ledgeriana. England, reluctant to purchase more trees that were possibly low in quinine content, refused to buy the seeds. The Dutch bought the seeds from Ledger, planted them in Java, and came to monopolize the worlds supply of quinine for close to 100 years. During World War II, the Japanese took control of Java. The Dutch took seeds out of Java but had no time to grow new trees to supply troops stationed in the tropics with quinine. The United States sent a group of botanists to Columbia to obtain enough quinine to use throughout the war. In 1944, synthetic quinine was developed by American scientists. Synthetic quinine proved to be very effective against malaria and had fewer side effects, and the need for natural quinine subsided. Over the years, the causative malarial parasite became resistant to synthetic quinine preparations. Interestingly, the parasites have not developed a full resistance to natural quinine.

Uses and manufacture

The chemical composition of quinine is C2OH24N2O2.H2O. Quinine is derived from cinchona bark, and mixed with lime. The bark and lime mixture is extracted with hot paraffin oil, filtered, and shaken with sulfuric acid. This solution is neutralized with sodium carbonate. As the solution cools, quinine sulfate crystallizes out. To obtain pure quinine, the quinine sulfate is treated with ammonia. Crystalline quinine is a white, extremely bitter powder. The powdered bark can also be treated with solvents, such as toluene, or amyl alcohol to extract the quinine. Current biotechnology has developed a method to produce quinine by culturing plant cells. Grown in test tubes that contain a special medium that contains absorbent resins, the cells can be manipulated to release quinine, which is absorbed by the resin and then extracted. This method has high yields but is extremely expensive and fragile.

Medicinally, quinine is best known for its treatment of malaria. Quinine does not cure the disease, but treats the fever and other related symptoms. Pharmacologically, quinine is toxic to many bacteria and one-celled organisms, such as yeast and plasmodia. It also has antipyretic (fever-reducing), analgesic (pain-relieving), and local anesthetic properties. Quinine concentrates in the red blood cells and is thought to interfere with the protein and glucose synthesis of the malaria parasite. With treatment, the parasites disappear from the blood stream. Many malarial victims have a recurrence of the disease because quinine does not kill the parasites living outside the red blood cells. Eventually, the parasites make their way into the blood stream, and the victim has a relapse. Quinine is also used to treat myotonic dystrophy (muscle weakness, usually facial) and muscle cramps associated with early kidney failure. The toxic side effects of quinine, called Cinchonism, include dizziness, tinnitus (ringing in ears), vision disturbances, nausea, and vomiting. Extreme effects of excessive quinine use include blindness and deafness.

Quinine also has nonmedicinal uses, such as in preparations for the treatment of sunburn. It is also used in liqueurs, bitters, and condiments. The best known nonmedicinal use is its addition to tonic water and soft drinks. The addition of quinine to water dates from the days of British rule in India-quinine was added to water as a prevention against malaria. About 40% of the quinine produced is used by the food and drug industry, the rest is used medicinally. In the United States, beverages made with quinine may contain not more than 83 parts per million cinchona alkaloids.

Resources

BOOKS

Gray, J. Man Against Disease-Preventive Medicine. New York: Oxford University Press, 1979.

Lewington, Anna. Plants for People. 2nd ed. London: Eden Project Books, 2004.

Rocco, Fiammetta. Quinine: Malaria and the Quest for a Cure That Changed the World. New York: Harper Perennial, 2004.

Christine Miner Minderovic

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Quinine

Quinine

Quinine, an extract from the bark of the chinchona tree found in Peru, Ecuador, and Bolivia. Indigenous peoples had long used ground chinchona bark to treat fever and cold and the name quinine comes from the Quechua term "quina" or "quinquina" meaning "bark" or "holy bark". Europeans in seventeenth-century South America came to recognize the native use, and in utilizing it found quinine to be effective in treating malaria. Samples were sent to Europe where chinchona bark's antimalarial value and demand grew. The Jesuits were particularly effective in organizing the early trade, and chinchona bark also came to be known as "Jesuits' bark." Thus quinine became the major antimalarial drug of the eighteenth and nineteenth centuries. Synthetic antimalarial drugs such as Atabrine, so important to the Allies during World War II, lessened but did not eliminate the reliance on quinine. Once quinine was a valuable commodity shipped from Peru to Europe, but its commercial value has been far less significant in world history than its medical value. With quinine, Europeans had a new weapon against the fevers of the tropics. Demographic and settlement patterns for Europeans and indigenous peoples changed as quinine brought malaria under control.

See alsoDiseases; Jesuits; Medicinal Plants; Medicine: Colonial Spanish America.

BIBLIOGRAPHY

Henry Hobhouse, Seeds of Change: Five Plants that Transformed Mankind (1985).

Additional Bibliography

Appel, John Wilton. Francisco José de Caldas: A Scientist at Work in Nueva Granada. Philadelphia: American Philosophical Society, 1994.

Jarcho, Saul, and Francesco Torti. Quinine's Predecessor: Francesco Torti and the Early History of Cinchona. Baltimore, MD: Johns Hopkins University Press, 1993.

Puerto Sarmiento, F. Javier. La ilusión quebrada: Botánica, sanidad y política científica en la España ilustrada. Barcelona: Serbal; Madrid: CSIC, 1988.

Rocco, Fiammetta. The Miraculous Fever Tree: Malaria and the Quest for a Cure that Changed the World. New York: HarperCollins, 2003.

Zárate, Carlos G. Extracción de quina: La configuración del espacio andino-amazónico de fines del siglo XIX. Bogotá: Universidad Nacional de Colombia, Sede Leticia, Instituto Amazónico de Investigaciones, 2001.

                                             John C. Super

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Quinine

Quinine

Quinine is an alkaloid obtained from the bark of several species of the cinchona tree . Until the development of synthetic drugs, quinine was used as the primary treatment of malaria , a disease that kills over 100 million people a year. The cinchona tree is native to the eastern slopes of the Andes Mountains in South America . Today, the tree is cultivated throughout Central and South America, Indonesia, India, and some areas in Africa . The cinchona tree contains more than 20 alkaloids of which quinine and quinidine are the most important. Quinidine is used to treat cardiac arrhythmias.


History

South American Indians have been using cinchona bark to treat fevers for many centuries. Spanish conquerors learned of quinine's medicinal uses in Peru, at the beginning of the seventeenth century. Use of the powdered " Peruvian bark" was first recorded in religious writings by the Jesuits in 1633. The Jesuit fathers were the primary exporters and importers of quinine during this time and the bark became known as " Jesuit bark." The cinchona tree was named for the wife of the Spanish viceroy to Peru, Countess Anna del Chinchón. A popular story is that the Countess was cured of the ague (a name for malaria the time) in 1638. The use of quinine for fevers was included in medical literature in 1643. Quinine did not gain wide acceptance in the medical community until Charles II was cured of the ague by a London apothecary at the end of the seventeenth century. Quinine was officially recognized in an edition of the London Pharmacopoeia as "Cortex Peruanus" in 1677. Thus began the quest for quinine. In 1735, Joseph de Jussieu, a French botanist, accompanied the first non-Spanish expedition to South America and collected detailed information about the cinchona trees. Unfortunately, as Jussieu was preparing to return to France, after 30 years of research, someone stole all his work. Charles Marie de la Condamine, leader of Jussieu's expedition, tried unsuccessfully to transfer seedlings to Europe . Information about the cinchona tree and its medicinal bark was slow to reach Europe. Scientific studies about quinine were first published by Alexander von Humboldt and Aimé Bonpland in the first part of the 18th century. The quinine alkaloid was separated from the powdered bark and named "quinine" in 1820 by two French doctors. The name quinine comes from the Amerindian word for the cinchona tree, quinaquina, which means "bark of barks." As European countries continued extensive colonization in Africa, India, and South America, the need for quinine was great, because of malaria. The Dutch and British cultivated cinchona trees in their East Indian colonies but the quinine content was very low in those species. A British collector, Charles Ledger, obtained some seeds of a relatively potent Bolivian species, Cinchona ledgeriana. England, reluctant to purchase more trees that were possibly low in quinine content, refused to buy the seeds. The Dutch bought the seeds from Ledger, planted them in Java, and came to monopolize the world's supply of quinine for close to 100 years. During World War II, the Japanese took control of Java. The Dutch took seeds out of Java but had no time to grow new trees to supply troops stationed in the tropics with quinine. The United States sent a group of botanists to Columbia to obtain enough quinine to use throughout the war. In 1944, synthetic quinine was developed by American scientists. Synthetic quinine proved to be very effective against malaria and had fewer side effects, and the need for natural quinine subsided. Over the years, the causative malarial parasite became resistant to synthetic quinine preparations. Interestingly, the parasites have not developed a full resistance to natural quinine.

Uses and manufacture

The chemical composition of quinine is C2OH2 4N2O2H2O. Quinine is derived from cinchona bark, and mixed with lime. The bark and lime mixture is extracted with hot paraffin oil, filtered, and shaken with sulfuric acid . This solution is neutralized with sodium carbonate . As the solution cools, quinine sulfate crystallizes out. To obtain pure quinine, the quinine sulfate is treated with ammonia . Crystalline quinine is a white, extremely bitter powder. The powdered bark can also be treated with solvents, such as toluene, or amyl alcohol to extract the quinine. Current biotechnology has developed a method to produce quinine by culturing plant cells. Grown in test tubes that contain a special medium that contains absorbent resins , the cells can be manipulated to release quinine, which is absorbed by the resin and then extracted. This method has high yields but is extremely expensive and fragile.

Medicinally, quinine is best known for its treatment of malaria. Quinine does not cure the disease, but treats the fever and other related symptoms. Pharmacologically, quinine is toxic to many bacteria and one-celled organisms, such as yeast and plasmodia. It also has antipyretic (fever-reducing), analgesic (pain-relieving), and local anesthetic properties. Quinine concentrates in the red blood cells and is thought to interfere with the protein and glucose synthesis of the malaria parasite. With treatment, the parasites disappear from the blood stream. Many malarial victims have a recurrence of the disease because quinine does not kill the parasites living outside the red blood cells. Eventually, the parasites make their way into the blood stream, and the victim has a relapse. Quinine is also used to treat myotonic dystrophy (muscle weakness, usually facial) and muscle cramps associated with early kidney failure. The toxic side effects of quinine, called Cinchonism, include dizziness, tinnitus (ringing in ears), vision disturbances, nausea, and vomiting. Extreme effects of excessive quinine use include blindness and deafness.

Quinine also has nonmedicinal uses, such as in preparations for the treatment of sunburn. It is also used in liqueurs, bitters, and condiments. The best known nonmedicinal use is its addition to tonic water and soft drinks. The addition of quinine to water dates from the days of British rule in India-quinine was added to water as a prevention against malaria. About 40% of the quinine produced is used by the food and drug industry, the rest is used medicinally. In the United States, beverages made with quinine may contain not more than 83 parts per million cinchona alkaloids.


Resources

books

Gray, J. Man Against Disease-Preventive Medicine. New York: Oxford University Press, 1979.

Lewington, Anna. Plants for People. New York: Oxford University Press, 1990.


Christine Miner Minderovic

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