The Role of Chemistry in History

Intro | Chemistry | Sources | Affects History | History affects  | Poor Countries | Undesired Effects  | Substitutes | Conclusion

 JMol Image:

Chemical Formula: C₂₀H₂₄N₂O₂

Quinine is soluble in alcohol, ether, chloroform, carbon disulfide, oils, glycerol, and acids; very slightly soluble in water.  Today, it is established that quinine is made of 20 carbon atoms, 24 hydrogen atoms, 2 nitrogen atoms and 2 oxygen atoms: C₂₀H₂₄N₂O₂. The two hexagonal rings represent the quinoline structure which is common to most quinine derivatives such as chloroquine.

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Intro | Chemistry | Sources | Affects History | History affects  | Poor Countries | Undesired Effects  | Substitutes | Conclusion

Quinine, in sum, is one the molecules that have had a tremendous impact on the history of mankind. Although its medicinal properties were known well before, it has been made popular thanks to the campaign of the Jesuits in the 17^th century. The understanding of its chemistry as well as periods of high demands have led to attempts towards its synthetic make up which has only been achieved in 2001. Because of its many side effects and the scarcity of its source, cheaper and better alternatives have been sought after. These substitutes, however, did not completely remove quinine from the list of the leading drugs for the treatment and prevention of the world number one killer disease. After the recent successful synthesis of this potent molecule, there is reason to believe that one day soon, the world may free itself from the malaria disease.

Bibliography: 

1.    Ball, Phillip. “History of science: Quinine steps back in time”. Nature: 2008. www.nature.com.
2. Barton, Patricia & Mills, James H. Drugs and empires: Essays in Modern Imperialism and Intoxication. Palgrave McMillan. New York: 2007.
3. Burreson, Jay & Le Couteur, Penny. Napoleon’s button: 17 molecules that changed history. Jeremy P. Tarcher/Penguin. New York: 2004.
4. Considine, Glenn D. Van Nostrand’s encyclopedia of chemistry. Wiley-Interscience. Hoboken, NJ: 2005.
5. Cotton, Simon. “The Mighty Quinine”. http://www.chm.bris.ac.uk. http://www.chm.bris.ac.uk/motm/quinine/quininev.htm
6. Dagani, Ron. Quinine. Chemical & Engineering News. Washington, DC: 2005. http://envoy.dickinson.edu:2048/login?url=http://proquest.umi.com/pqdweb?did=857229151&sid=3&Fmt=2&clientId=4534&RQT=309&VName=PQD
7. Duran-Reynals. The fever bark tree. Double Day and Company. Garden City: 1946.
8. Frankel, S. Herbert. The economic impact on underdeveloped countries: Essay on international investment and social change. Harvard University Press. Cambridge: 1955.
9. Isaacman, Allen & Roberts, Richard. Cotton, Colonialism, and Social History in Sub-Saharan Africa. Heinemann. Portsmouth, NH: 1995.
10. Keen, Mary. The dark side of the vegetable world. The Spectator. London: 1999. http://envoy.dickinson.edu:2048/login?url=http://proquest.umi.com/pqdwep?did=42416027&sid=1&Fmt=3&clientId=4534&RQT=309&VName=PPQ
11.  Magill, Alan & Panosian Claire. Making Antimalarial Agents Available in the United States. The New England Journal of Medicine. Boston: 2005. http://envoy.dickinson.edu:2048/login?url=http://proquest.umi.com/pqdweb?did=875776471&sid=8&Fmt=3&clientId=4534&RQT=309&VName=PQD
12. Mahar, Dulcy. Homes & Garden of the Northwest. The Orgonian. Portaland, Or: 2003. http://envoy.dickinson.edu:2048/login?url=http://proquest.umi.com/pqdweb?did=489774871&sid=1&Fmt=3&clientId=4534&RQT=309&VName=PQD
13. Rinsky, Rober A. Public Health Reports: Historical Collection 1878-2005. Association of Schools of Public Health. Washington DC: 2005.
14. Werner, Louis. Quinine’s: Feverish tales and trails. Americas. Washington, DC: 2003. http://envoy.dickinson.edu:2048/login?url=http://proquest.umi.com/pqdweb?did=419274271&sid=2&Fmt=4&clientId=4534&RQT=309&VName=PQD
15.  Williams, Stephen. The Fever Trail. African Business. London: 2002. http://envoy.dickinson.edu:2048/login?url=http://proquest.umi.com/pqdweb?did=105869691&sid=1&Fmt=4&clientId=4534&RQT=309&VName=PQD

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Intro | Chemistry | Sources | Affects History | History affects  | Poor Countries | Undesired Effects  | Substitutes | Conclusion

Over the past few decades, chloroquine-resistant strains of the malaria parasite have spread very rapidly. This has reduced the effectiveness of chloroquine and other quinine related drugs.

Drugs like fansidar, and mefloquine are often used as substitutes.

These drugs, however, are highly toxic with, sometimes, allarming side effects.

Therefore, quinine still remains one of the leading drugs for the treatment and prevention of malaria.

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Intro | Chemistry | Sources | Affects History | History affects  | Poor Countries | Undesired Effects  | Substitutes | Conclusion

Quinine may be harmful if wrongly used and/or depending on the tolerability of the patient.

• Certain patients may vomit after ingesting malaria tablets 

• If accidentally injected in nerves, it can paralyze

• It is extremely toxic in overdose

• In the U.S. it is classified as a Category X teratogen by the Food and Drugs Adminsitration: It can cause birth defects if taken by pregnant woman

• It can be itchy

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Intro | Chemistry | Sources | Affects History | History affects  | Poor Countries | Undesired Effects  | Substitutes | Conclusion

Breeding place for mosquitoes

• Malaria is number one killer in many developping countires

• Every year hundreds of millions suffer from malaria and 2 to 3 million of them die, mainly in Africa.

Adavantages of Quinine:

• Quinine still being used in many developping countries as treatment against malaria

• It is accessible and affordable, but not always reliable.

• In many countries they have a lot of fake pills.

Disadvantages:

• The quinine molecule has been instrumental in the exploitation of many developping countries.

• The bark of the cinchona tree has brought barely any economic benefit to the indigenous people of the Andes.

 “Outsiders benefited from the the quinine molecule, exploiting a unique resource of a less developped country for their own advsantage”.

Napoleon’s Buttons: p.348-349.

• Without quinine, most of today’s developping countries would not have been colonized and exploited for so long.
• Finally, despite the existence of quinine and other drugs, malaria still is rife in poor countries.
• There are conditions which facilitate the reproduction of the mosquitoes.
• With such favorable conditions for its development, the parasite develops resitant forms to antimalarial drugs.

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Intro | Chemistry | Sources | Affects History | History affects  | Poor Countries | Undesired Effects  | Substitutes | Conclusion

 The Jesuit Powder:

• Before 1655, each time a papal conclave was held in Rome a number of the cardinals would die from malaria.

• In 1633,  a number of the Jesuit order in Peru began using the Cinchona bark to treat and prevent malaria.

• In 1940 Father Bartolome Tafur took some of the bark with him to Rome and words of  its miraculous effects were spread out very quickly.

• In the 1955 papal conclave, thanks to the cinchonal bark, no cardinal died.

• The Cinchona bark became then known as the Jesuit’s powder, as the Jesuits started importing large amounts and selling it through Europe.

• It became very popular from that time on.

World War II:

• During World War II, there was high demand for quinine.

• Extensive research led to the discovery of a derivative of quinine: chloroquine.

• Both quinine and chloroquine have the quinoline structure.

                      Quinine                           

                                                                      Chloroquine

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Introduction to Quinine | Properties of Quinine | A brief History of Quinine | History affects Quinine | Quinine affects History | Quinine and Third World Countries | Undesired Effects of Quinine | Substitutes of Quinine | Conclusion

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Intro | Chemistry | Origin | Affects History | History affects  | Poor Countries | Undesired Effects  | Substitutes | Conclusion

Soldiers taking daily dose of quinine

Colonization:

• Without quinine, the colonization of many African and Asian countries would not have been possible.

• Malaria is very common in these areas and therefore European powers relied heavily on their supplies of quinine to keep them under control.

Gin and Tonic:

• Gin and Tonic was introduced by the Birtish East India Company in India, in the 18th century.

• Tonic water contains quinine and is used to prevent malaria.

• Because tonic water was very bitter, gin was added to make the water more palatable.

• This has become and still is a popular drink

Second World War:

• The discovery of the source of quinine, the Cinchona tree, has created very profitable commerce for countries like Bolivia, Ecuador, Peru and Colombia. They banned the export of the tree in order to monopolize the commerce.

• Species of the tree were eventually smuggled out. In 1861, the Dutch bought a pound of the species known as Cinchona Ledgeriana from an Australian trader named Charles Ledger.

• The species turned to be the most most productive with quinine level as high as 13% compared to the usual 3%. C. Ledgeriana was cultivated in Java.

• In 1940, the quinine molecule tipped the scale of the war as Germany attacked the Netherlands to confiscate the entire European stock of quinine.

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Intro | Chemistry | Sources | Affects History | History affects  | Poor Countries | Undesired Effects  | Substitutes | Conclusion

•  Natural Source: The Cinchona Tree
  • It was not generally known which plant Quinine came from.
  • In 1735, a French botanist discovered the source as Cinchona tree.
  • Harvesting the bark of Chinchona then became major industry.
  • High demand  and low supply drove prices up.
  • Isolating and identifying the molecule became a big research field.

“High in the Andes, between three thousand and nine thousand feet above sea level, there grows a tree whose bark contains an alkaloid molecule, without which the world would be a very different place today”.

Napoleon’s Buttons: P.332

• Synthetic Makeup:

“No matter how much the evidence points to the correctness of a proposed structure, to be absolutely sure it is correct, you have to synthesize the molecule by an independent route”.

Napoleon’s Buttons: P.340

• • Quinine is belived to be first  isolated in 1792, maybe in its impure form.
  • In 1820, French researchers Joseph Pelletier and Joseph Caventou identified and purified quinine.
  • Structure of quinine not fully understood until 2oth century.
  • First attempts to synthetize were unsuccessful.
  • In 1856, English chemist William Perkin combined allyltoluidine with 3 oxygens to make quinine.
  • He thought: 2C₁₀H₁₃N + 3O = C₂₀H₂₄N₂O₂ + H₂O.
  • Instead, he made “mauve” and a lot of “money”.
  • In 1944 Robert Woodward and William Doering of Harvard presumably completed the synthesis of quinine.
  • They were able to convert a quinoline derivative into a molecule that, allegedely, was successfully transformed into quinine in 1918.
  • The report about this earlier work, however, could not be ascertained.
  • Finally, in 2001, Gilbert Stork from Columbia University and coworkers were able to synthesize quinine by going through all the steps themselves

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Intro | Chemistry | Sources | Affects History | History affects  | Poor Countries | Undesired Effects  | Substitutes | Conclusion

Malaria, which comes from the Italian mal aria meaning bad air, is a disease caused by a microscopic parasite transmitted from one patient to another by the anopheles mosquito. References to this disease can be found in written records of China, India and Egypt dating from as far back as thousands of years.  Believed to be perhaps the greatest killer of humanity of all time, malaria remains a big concern especially in third world countries where it claims millions of lives every year. The first effective treatment against this disease is quinine, a natural white crystalline alkaloid extracted from the cinchona bark. Thanks to its medicinal properties, quinine has saved millions of lives and has had a tremendous impact on the history of the world as we know it.

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