Editing Quinine (section)

== Uses ==

=== Medical ===
As of 2006, quinine is no longer recommended by the [[World Health Organization]] (WHO) as a first-line treatment for [[malaria]], because there are other substances that are equally effective with fewer side effects. They recommend that it be used only when [[artemisinin#Artemisinin derivatives|artemisinins]] are not available.{{why|reason=Because of increasing malaria resistance to the drug?|date=March 2024}}<ref>{{cite web|author=World Health Organization|title=Guidelines for the treatment of malaria|publisher=World Health Organization|url=http://apps.who.int/malaria/docs/TreatmentGuidelines2006.pdf|year=2006|access-date=10 August 2009|url-status=dead|archive-url=https://web.archive.org/web/20090805225019/http://apps.who.int/malaria/docs/TreatmentGuidelines2006.pdf|archive-date=5 August 2009}}</ref><ref>{{cite journal | vauthors = Dondorp A, Nosten F, Stepniewska K, Day N, White N | title = Artesunate versus quinine for treatment of severe falciparum malaria: a randomised trial | journal = Lancet | volume = 366 | issue = 9487 | pages = 717–725 | year = 2005 | pmid = 16125588 | doi = 10.1016/S0140-6736(05)67176-0 | s2cid = 173027 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Reyburn H, Mtove G, Hendriksen I, von Seidlein L | title = Oral quinine for the treatment of uncomplicated malaria | journal = BMJ | volume = 339 | pages = b2066 | date = July 2009 | pmid = 19622550 | doi = 10.1136/bmj.b2066 | s2cid = 206891479 | url = https://researchonline.lshtm.ac.uk/id/eprint/5019/1/Oral%20quinine%20for%20the%20treatment%20of%20uncomplicated%20malaria%20_%20The%20BMJ.pdf }}</ref><ref>{{cite journal | vauthors = Achan J, Tibenderana JK, Kyabayinze D, Wabwire Mangen F, Kamya MR, Dorsey G, D'Alessandro U, Rosenthal PJ, Talisuna AO | title = Effectiveness of quinine versus artemether-lumefantrine for treating uncomplicated falciparum malaria in Ugandan children: randomised trial | journal = BMJ | volume = 339 | pages = b2763 | date = July 2009 | pmid = 19622553 | pmc = 2714631 | doi = 10.1136/bmj.b2763 }}</ref> Quinine is also used to treat [[Systemic lupus erythematosus|lupus]] and [[arthritis]].

Quinine was frequently prescribed as an [[off-label]] treatment for [[Cramps#Nocturnal leg cramps|leg cramps at night]], but this has become less common since 2010 due to a warning from the US [[Food and Drug Administration]] (FDA) that such practice is associated with life-threatening side effects.<ref name="FDA Safety Communication">{{cite web | url = https://www.fda.gov/drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm218202.htm | title = FDA Drug Safety Communication: New risk management plan and patient Medication Guide for Qualaquin (quinine sulfate) | access-date = 21 February 2011 | date = 7 August 2010 | publisher = U.S. [[Food and Drug Administration]] (FDA) | url-status = live | archive-url = https://web.archive.org/web/20110219065903/https://www.fda.gov/drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm218202.htm | archive-date = 19 February 2011}}</ref><ref name="FDA risks">{{cite web | title=Serious risks associated with using Quinine to prevent or treat nocturnal leg cramps (September 2012) | website=U.S. [[Food and Drug Administration]] (FDA)| date=31 August 2012 | url=https://www.fda.gov/ForHealthProfessionals/LearningActivities/ucm317811.htm | archive-url=https://web.archive.org/web/20161022135438/https://www.fda.gov/ForHealthProfessionals/LearningActivities/ucm317811.htm | archive-date=22 October 2016 | url-status=dead | access-date=19 January 2020}}</ref><ref>{{Cite web|url=https://www.consumerreports.org/cro/2012/04/quinine-for-night-time-leg-cramps-no-longer-recommended/index.htm|title=Quinine for Night-Time Leg Cramps |website=[[Consumer Reports]]|access-date=20 January 2020}}</ref> Quinine can also act as a competitive inhibitor of [[monoamine oxidase]] (MAO), an enzyme that removes neurotransmitters from the brain. As an [[Monoamine oxidase inhibitor|MAO inhibitor]], it has potential to serve as a treatment for individuals with psychological disorders, similar to antidepressants that inhibit MAO.<ref>{{cite journal | vauthors = Mitsui N, Noro T, Kuroyanagi M, Miyase T, Umehara K, Ueno A | title = Monoamine oxidase inhibitors from Cinchonae Cortex | journal = Chemical & Pharmaceutical Bulletin | volume = 37 | issue = 2 | pages = 363–366 | date = February 1989 | pmid = 2743481 | doi = 10.1248/cpb.37.363 | doi-access = free }}</ref>

====Available forms====
Quinine is a basic [[amine]] and is usually provided as a salt. Various existing preparations include the [[hydrochloride]], dihydrochloride, [[sulfate]], bisulfate and [[gluconate]]. In the United States, quinine sulfate is commercially available in 324&nbsp;mg tablets under the brand name Qualaquin.

All quinine salts may be given orally or [[Intravenous therapy|intravenous]]ly (IV); quinine gluconate may also be given [[intramuscular injection|intramuscular]]ly (IM) or rectally (PR).<ref name="Barennes1996">{{cite journal | vauthors = Barennes H, Pussard E, Mahaman Sani A, Clavier F, Kahiatani F, Granic G, Henzel D, Ravinet L, Verdier F | title = Efficacy and pharmacokinetics of a new intrarectal quinine formulation in children with Plasmodium falciparum malaria | journal = British Journal of Clinical Pharmacology | volume = 41 | issue = 5 | pages = 389–395 | date = May 1996 | pmid = 8735679 | pmc = 2042609 | doi = 10.1046/j.1365-2125.1996.03246.x }}</ref><ref name="Barennes2006">{{cite journal | vauthors = Barennes H, Balima-Koussoubé T, Nagot N, Charpentier JC, Pussard E | title = Safety and efficacy of rectal compared with intramuscular quinine for the early treatment of moderately severe malaria in children: randomised clinical trial | journal = BMJ | volume = 332 | issue = 7549 | pages = 1055–1059 | date = May 2006 | pmid = 16675812 | pmc = 1458599 | doi = 10.1136/bmj.332.7549.1055 }}</ref> The main problem with rectal administration is that the dose can be expelled before it is completely absorbed; in practice, this is corrected by giving a further half dose. No injectable preparation of quinine is licensed in the US; [[quinidine]] is used instead.<ref>{{cite journal | vauthors = ((Centers for Disease Control and Prevention)) | title = Treatment with quinidine gluconate of persons with severe Plasmodium falciparum infection: discontinuation of parenteral quinine from CDC Drug Service | journal = MMWR. Recommendations and Reports | volume = 40 | issue = RR-4 | pages = 21–23 | date = April 1991 | pmid = 1850497 | url = https://www.cdc.gov/mmwr/preview/mmwrhtml/00043932.htm }}</ref><ref>{{cite journal | vauthors = Magill A, Panosian C | title = Making antimalarial agents available in the United States | journal = The New England Journal of Medicine | volume = 353 | issue = 4 | pages = 335–337 | date = July 2005 | pmid = 16000347 | doi = 10.1056/NEJMp058167 | author-link2 = Claire Panosian | doi-access = free }}</ref>

{| class="wikitable"
|+'''Quinine base in various salts'''
!Name
!Amount equivalent to 100&nbsp;mg quinine base
|-
|Quinine base
|100&nbsp;mg
|-
|Quinine bisulfate
|169&nbsp;mg
|-
|Quinine dihydrochloride
|122&nbsp;mg
|-
|Quinine gluconate
|160&nbsp;mg
|-
|Quinine hydrochloride
|111&nbsp;mg
|-
|Quinine sulfate dihydrate [(quinine)<sub>2</sub>H<sub>2</sub>SO<sub>4</sub>∙2H<sub>2</sub>O]
|121&nbsp;mg
|}

===Beverages===
{{See also|Tonic water}}
[[File:Tonic water uv.jpg|thumb|[[Tonic water]], in normal light and ultraviolet "[[black light]]". The quinine content of tonic water causes it to [[fluorescence|fluoresce]] under black light.]]
Quinine is a flavor component of [[tonic water]] and [[bitter lemon]] [[soft drinks]]. On the [[soda gun]] behind many bars, tonic water is designated by the letter "Q" representing quinine.<ref>{{cite book | vauthors = Charming C |title=Miss Charming's Guide for Hip Bartenders and Wayout Wannabes |page=189 |year=2006 |publisher=Sourcebooks, Inc. |location=USA |isbn=978-1-4022-0804-1 }}</ref>

Tonic water was initially marketed as a means of delivering quinine to consumers in order to offer anti-malarial protection. According to tradition, because of the bitter taste of anti-[[malaria]]l quinine tonic, British colonials in India mixed it with [[gin]] to make it more palatable, thus creating the [[gin and tonic]] cocktail, which is still popular today.<ref>{{cite web | vauthors = Khosla S |title=Gin and Tonic: The fascinating story behind the invention of the classic English cocktail |url=https://www.india.com/lifestyle/gin-and-tonic-the-fascinating-story-behind-the-invention-of-the-classic-english-cocktail-1934782/ |website=India.com |access-date=8 June 2019|date=17 March 2017 }}</ref> While it is possible to drink enough tonic water to temporarily achieve quinine levels that offer anti-malarial protection, it is not a sustainable long-term means of protection.<ref>{{cite journal | vauthors = Meyer CG, Marks F, May J | title = Editorial: Gin tonic revisited | journal = Tropical Medicine & International Health | volume = 9 | issue = 12 | pages = 1239–1240 | date = December 2004 | pmid = 15598254 | doi = 10.1111/j.1365-3156.2004.01357.x | s2cid = 24261782 | doi-access = free }}</ref>

In France, quinine is an ingredient of an {{lang|fr|[[apéritif]]}} known as {{lang|fr|[[quinquina]]}}, or ''"Cap Corse"'', and the wine-based {{lang|fr|apéritif}} [[Dubonnet]]. In Spain, quinine (also known as "Peruvian bark" for its origin from the native cinchona tree) is sometimes blended into sweet [[Malaga (wine)|Malaga wine]], which is then called ''"Malaga Quina"''. In Italy, the traditional flavoured wine [[Barolo#Barolo Chinato|Barolo Chinato]] is infused with quinine and local herbs, and is served as a {{Lang|fr|[[digestif]]}}. In Britain, the company [[A.G. Barr]] uses quinine as an ingredient in the carbonated and [[caffeinated beverage]] [[Irn-Bru]]. In Uruguay and Argentina, quinine is an ingredient of a [[PepsiCo]] tonic water named [[Paso de los Toros (drink)|Paso de los Toros]]. In Denmark, it is used as an ingredient in the carbonated sports drink [[Faxe Kondi]] made by [[Royal Unibrew]].

As a flavouring agent in drinks, quinine is limited to 83&nbsp;[[Parts per million|ppm]] ({{nowrap|83 mg/L}}) in the United States,<ref>{{cite journal | vauthors = Ballestero JA, Plazas PV, Kracun S, Gómez-Casati ME, Taranda J, Rothlin CV, Katz E, Millar NS, Elgoyhen AB | title = Effects of quinine, quinidine, and chloroquine on alpha9alpha10 nicotinic cholinergic receptors | journal = Molecular Pharmacology | volume = 68 | issue = 3 | pages = 822–829 | date = September 2005 | pmid = 15955868 | doi = 10.1124/mol.105.014431 | s2cid = 26907917 }}</ref><ref>{{cite web |title=21 CFR 172.575 -- Quinine. |url=https://www.ecfr.gov/current/title-21/chapter-I/subchapter-B/part-172/subpart-F/section-172.575 |website=www.ecfr.gov |language=en}}</ref> to 85&nbsp;mg/L in Taiwan,<ref>{{cite web |title=食品添加物使用範圍及限量暨規格標準 |url=https://rc.csmu.edu.tw/var/file/18/1018/img/1581/339191880.pdf |date=2020-04-14|page=104}}</ref> and to 100&nbsp;mg/L in the European Union.<ref>{{cite journal |title=Scientific Opinion on Flavouring Group Evaluation 35, Revision 1 (FGE.35Rev1): Three quinine salts from the Priority list from chemical group 30 |journal=EFSA Journal |date=September 2015 |volume=13 |issue=9 |doi=10.2903/j.efsa.2015.4245|doi-access=free }}</ref><ref>{{cite web|title=COMMISSION IMPLEMENTING REGULATION (EU) No 872/2012|url=http://eur-lex.europa.eu/legal-content/EN/TXT/?qid=1507509835974&uri=CELEX:32012R0872|website=EUR-Lex|publisher=Official Journal of the European Union|access-date=9 October 2017}}</ref>

Direct use of [[cinchona bark]] in beverages is also allowed in the US, with a maximum allowded total cinchona alkaloid level of 83&nbsp;ppm in the finished beverage.<ref>{{cite web |title=21 CFR 172.510 -- Natural flavoring substances and natural substances used in conjunction with flavors. |url=https://www.ecfr.gov/current/title-21/chapter-I/subchapter-B/part-172/subpart-F/section-172.510 |website=www.ecfr.gov |language=en |quote=Cinchona, red, bark}}</ref>

===Scientific===
Quinine (and [[quinidine]]) are used as the [[chirality (chemistry)|chiral]] [[Moiety (chemistry)|moiety]] for the [[ligand]]s 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 (metrology)|standard]].<ref name="books.google.co.in">{{cite book| vauthors = Lakowicz JR |authorlink=Joseph R. Lakowicz|title=Principles of Fluorescence Spectroscopy|url=https://books.google.com/books?id=-PSybuLNxcAC|edition=3rd|year=2006|publisher=Springer Science & Business Media|isbn=978-0-387-46312-4|page=54|chapter=2. Instrumentation for Fluorescence Spectroscopy}}</ref><ref name="Quinine sulfate">{{cite web | vauthors = Prahl S |title=Quinine sulfate |url=https://omlc.org/spectra/PhotochemCAD/html/081.html |website=OMLC |access-date=16 August 2013}}</ref>