Editing Cinchona (section)

==Chemistry==
===Cinchona alkaloids===
[[File:Cinchona alkaloids.svg|thumb|General structure of ''Cinchona'' alkaloids]]
The bark of trees in this genus is the source of a variety of [[alkaloid]]s, the most familiar of which is [[quinine]], an [[antipyretic]] (antifever) agent especially useful in treating malaria.{{sfn|Chisholm|1911}}{{sfn|EA|1920}} For a while the extraction of a mixture of alkaloids from the cinchona bark, known in India as the cinchona febrifuge, was used. The alkaloid mixture or its sulphated form mixed in alcohol and sold as quinetum was however very bitter and caused nausea, among other side effects.<ref>{{cite journal|pmc=5130665|year=1878|title=Cinchona Febrifuge|journal=The Indian Medical Gazette|volume=13|issue=4|pages=107–108|pmid=28997438}}</ref>

Cinchona alkaloids include:
* [[cinchonine]] and [[cinchonidine]] ([[stereoisomer]]s with R<sup>1</sup> = [[Vinyl group|vinyl]], R<sup>2</sup> = [[hydrogen]])
* [[quinine]] and [[quinidine]] ([[stereoisomer]]s with R<sup>1</sup> = vinyl, R<sup>2</sup> = [[methoxy]])
* [[dihydroquinine]] and [[dihydroquinidine]] (stereoisomers with R<sup>1</sup> = [[ethyl group|ethyl]], R<sup>2</sup> = methoxy)

They find use in [[organic chemistry]] as [[organocatalyst]]s in [[asymmetric synthesis]].

===Other chemicals===
Alongside the alkaloids, many cinchona barks contain [[cinchotannic acid]], a particular [[tannin]], which by oxidation rapidly yields a dark-coloured phlobaphene<ref>{{cite book
| chapter-url=http://chestofbooks.com/health/materia-medica-drugs/Textbook-Materia-Medica/Cinchona-Bark-Cortex-Cinchonae-Part-3.html
| chapter=Cinchona Bark (Cortex Cinchonae). Part 3
| title=A Text Book of Materia Medica, Being An Account of the More Important Crude Drugs of Vegetable And Animal Origin
| author= Henry G. Greenish
| asin=B000J31E44
| publisher=J. & A. Churchill
| year=1920
}}
</ref> called red cinchonic,<ref>{{cite book
| chapter-url=http://chestofbooks.com/health/materia-medica-drugs/The-Essentials-Therapeutics/Cinchonaceae-Part-2.html
| title=Essentials of Materia Medica And Therapeutics
| author=Alfred Baring Garrod
| isbn=978-1-4326-8837-0
| chapter=Cinchonaceae. Part 2
| publisher=Kessinger Publishing
| year=2007
}}
</ref> cinchono-fulvic acid, or cinchona red.<ref>{{cite book
| title=Encyclopædia Britannica
| year=1902
| chapter-url=http://www.1902encyclopedia.com/Q/QUI/quinine.html
| edition=10
| chapter=Quinine
| title-link=Encyclopædia Britannica
}}
</ref>

In 1934, efforts to make malaria drugs cheap and effective for use across countries led to the development of a standard called "totaquina" proposed by the Malaria Commission of the [[League of Nations]]. Totaquina required a minimum of 70% crystallizable alkaloids, of which at least 15% was to be quinine with not more than 20% amorphous alkaloids.<ref>{{cite journal|doi=10.1038/145458b0|title=Totaquina|journal=Nature|volume=145|issue=3673|pages=458|year=1940|bibcode=1940Natur.145R.458.|doi-access=free}}</ref><ref>{{cite journal| title=The Preparation, Analysis and Standardisation of Totaquina| author1=Groothoff, A.| author2=Henry, T.A.| journal= Rivista di Malariologia |year=1933 |volume=12 |issue=1 |pages=87–91}}</ref>