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Overview of malaria
Malaria is caused by Plasmodium falciparum.
It is transmitted by female Anopheles mosquito from one person to the other.
Others routes of transmission:
- blood transfusion
- organ transplant
- shared use of needles or syringes contaminated with blood
- a mother to her unborn infant before or during delivery ("congenital" malaria).
Overview of malaria
Common signs and symptoms:
- High fever
- Chills
- Headache
- Nausea
- Vomiting
- Body aches
- Anemia
Prevention includes:
- Insecticide bed nets
- Insects repellents
- Long sleeves shirts
- Drugs such as Chloroquine, Atovaquone, and Proguanil.
Overview of malaria
Treatments differ from countries and regions.
Antimalarial medications such as:
- Artemisinin
- Artesunate
- Artemether
- Quinine
Quinine
Molecular Formula: C20H24N2O2
Average mass: 324.417 Da
Monoisotopic mass: 324.183777 Da
Systematic Name: (8α,9R)-6'- Methoxycinchonan-9-ol
Structure includes quinoline and quinuclidine rings
Four asymmetric centers N
OH
H
N
H
H
H3CO
CH2:CH2
9R
8S
34
http://pubs.acs.org/cen/img/83/i25/8325quinine.gif
http://www.malariajournal.com/content/figures/1475-2875-2-26-1.jpg
Quinine: background
• Discovered in 17th century by Jesuits
• Part of plant used
• Properties
• Others uses
• History of its Synthesis
Bark of the cinchona tree
http://www.chemistryviews.org/SpringboardWebApp/userfiles/chem/image/2013/2013_05/Bild2.jpg
Synthesis
• 1817: First isolation of quinine from cinchona tree bark by Pierre Joseph Pelletier and Joseph Caventou.
• 1853: Quinotoxine (or quinicine in older literature) obtained by acid catalyzed isomerization of quinine by Louis Pasteur.
http://en.wikipedia.org/wiki/File:QuininePasteur.png
Synthesis
• 1856: synthesis of quinine by William Henry Perkin
http://en.wikipedia.org/wiki/File:QuininePerkinsAttempt.png
Published in: Karina Ap. F. D. Souza; Paulo A. Porto; J. Chem. Educ. 2012, 89, 58-63.DOI: 10.1021/ed1003542Copyright © 2011 The American Chemical Society and Division of Chemical Education, Inc.
Scheme 4. Smith and Williams’ (2008) Procedure for Conversion of D-Quinotoxine to Quinine
Entry Reducing conditions Temp.(°C)
Isolated yield ofquinine/quinidine
yield ofquinine
1 DIBAL-H benzene 20 72% 33%2 NaBH4, EtOH 0 11% 4%
3 Al powder (new) NaOEt, EtOH
reflux trace trace
4 Al powder (new) NaOEt, EtOH
reflux 30% (1.1:1) 16%
5 Al powder + Al2O3 NaOEt, EtOH
reflux 26% (1.1:1) 14%
6 Al powder (aerated) NaOEt, EtOH
reflux 24% (1.1:1) 13%
7 Al powder MeOH, NaOMe
reflux 8% (1.2:1) 4%
8 Al powder (sonication) NaOEt, EtOH
reflux 22% (1.1:1) 12%
9 Al powder, Na(OiPr), i-PrOH
reflux 32% (1:1.2) 15%
10 Al(Oi-Pr)3, iPrOH reflux 28% 16%
11 LiAlH4, ether −78 45% trace
12 LiAlH4, ether 0 59% trace
13 LiAlH4, ether 20 56% trace
14 LiAlH4, ether 0 40% (1:1.5) 16%
Conditions for reducing quinidinone/quininone to quinine.
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3085927/table/T1/
How does quinine work ?
• Mechanism of action
- Interaction with the organism
- Interaction in body
- Side effects such as nausea, decreased hearing, dizziness, blurred vision, hypoglycemia, death by pulmonary edema, constipation, erectile dysfunction, or diarrhea.
Writing Assignment
My writing assignment will consist of a brochure to educate people on not only malaria and the treatments that are available, but also to raise an awareness of its devastation effects in the places where it exists today.
Works Cited
• Ron Dagani, Chem. Eng. News Archive, 2005, 83 (25), p 106 Publication Date (Print): June 20, 2005
• Karina Ap. F. D. Souza and Paulo A. Porto, “History and Epistemology of Science in the Classroom: The Synthesis of Quinine as a Proposal”, J. Chem. Educ., 2012, 89 (1), pp 58–63
• Bohórquez E, Chua M, Meshnick S. Quinine localizes to a non-acidic compartment within the food vacuole of the malaria parasite Plasmodium falciparum. Malaria Journal [serial online]. October 22, 2012;11:350. Available from: MEDLINE with Full Text, Ipswich, MA. Accessed November 16, 2014.
• Sanchez C, Stein W, Lanzer M. Dissecting the components of quinine accumulation in Plasmodium falciparum. Molecular Microbiology [serial online]. March 2008;67(5):1081-1093. Available from: MEDLINE with Full Text, Ipswich, MA. Accessed November 17, 2014.
• www.malariajournal.com/content/2/1/26 • http://www.chemspider.com/Chemical-Structure.84989.html (accessed 02:49, Oct 28, 2014)
• www.webmd.com/drugs/2/drug-869/quinine-sulfate.../details
• www.ncbi.nlm.nih.gov/... National Center for Biotechnology Information
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