ChemWiki - User contributions [en]

It:Quinine

2006-12-08T15:43:29Z

Jf205:

== Overview ==
'''Quinine''' is a widely used compound, the has been utilised for centuries for it's wondrous healing properties and delicious, tonic watery taste. In it's long history, no-one is yet to find a better way of enjoying '''quinine''' without the addition of a dash of gin and slice of lime. Research into '''quinine''' is still ongoing, hoping to unravel it's properties and find a way to exploit the wondrous powers.

== Structure ==

{| class="toccolours" border="1" style="fix: right; clear: left; margin: 1 1 1em 1em; border-collapse: collapse;"
|+ '''Quinine'''
! [[Image:quinine.gif|left|frame|300|Quinine: Your friend and mine]]
|
<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>;
<script>zoom 90; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
title 1
title 2
ATOM 1 C1 MOL 1 14.837 11.528 -0.146 1.00 0.00
ATOM 2 O2 MOL 1 15.046 10.948 -1.441 1.00 0.00
ATOM 3 C3 MOL 1 13.411 12.171 -0.177 1.00 0.00
ATOM 4 C4 MOL 1 16.150 12.284 0.311 1.00 0.00
ATOM 5 C5 MOL 1 12.955 13.632 -0.059 1.00 0.00
ATOM 6 C6 MOL 1 12.453 11.254 -0.277 1.00 0.00
ATOM 7 N7 MOL 1 17.263 11.339 0.387 1.00 0.00
ATOM 8 C8 MOL 1 16.625 13.393 -0.735 1.00 0.00
ATOM 9 C9 MOL 1 11.633 13.867 -0.052 1.00 0.00
ATOM 10 C10 MOL 1 13.862 14.798 0.039 1.00 0.00
ATOM 11 C11 MOL 1 11.057 11.615 -0.267 1.00 0.00
ATOM 12 C12 MOL 1 18.319 12.122 1.176 1.00 0.00
ATOM 13 C13 MOL 1 18.308 10.946 -0.600 1.00 0.00
ATOM 14 C14 MOL 1 18.185 13.590 -0.690 1.00 0.00
ATOM 15 C15 MOL 1 11.115 15.226 0.060 1.00 0.00
ATOM 16 N16 MOL 1 10.703 12.826 -0.153 1.00 0.00
ATOM 17 C17 MOL 1 13.376 16.043 0.127 1.00 0.00
ATOM 18 C18 MOL 1 18.563 13.571 0.746 1.00 0.00
ATOM 19 C19 MOL 1 18.825 12.284 -1.364 1.00 0.00
ATOM 20 C20 MOL 1 11.942 16.258 0.144 1.00 0.00
ATOM 21 O21 MOL 1 14.218 17.169 0.199 1.00 0.00
ATOM 22 C22 MOL 1 20.018 13.868 1.068 1.00 0.00
ATOM 23 C23 MOL 1 15.604 16.827 0.156 1.00 0.00
ATOM 24 C24 MOL 1 20.776 14.626 0.276 1.00 0.00
ATOM 25 H25 MOL 1 16.001 12.672 1.329 1.00 0.00
ATOM 26 H54 MOL 1 14.757 10.923 0.646 1.00 0.00
ATOM 27 H56 MOL 1 15.950 10.521 -1.473 1.00 0.00
ATOM 28 H58 MOL 1 12.708 10.291 -0.360 1.00 0.00
ATOM 29 H60 MOL 1 16.358 13.108 -1.656 1.00 0.00
ATOM 30 H62 MOL 1 16.180 14.261 -0.513 1.00 0.00
ATOM 31 H64 MOL 1 14.851 14.654 0.041 1.00 0.00
ATOM 32 H66 MOL 1 10.361 10.902 -0.351 1.00 0.00
ATOM 33 H68 MOL 1 18.035 12.134 2.135 1.00 0.00
ATOM 34 H70 MOL 1 19.187 11.632 1.091 1.00 0.00
ATOM 35 H72 MOL 1 19.073 10.511 -0.125 1.00 0.00
ATOM 36 H74 MOL 1 17.920 10.306 -1.264 1.00 0.00
ATOM 37 H76 MOL 1 18.483 14.428 -1.147 1.00 0.00
ATOM 38 H78 MOL 1 10.127 15.380 0.074 1.00 0.00
ATOM 39 H80 MOL 1 18.036 14.286 1.206 1.00 0.00
ATOM 40 H82 MOL 1 19.822 12.335 -1.301 1.00 0.00
ATOM 41 H84 MOL 1 18.553 12.241 -2.325 1.00 0.00
ATOM 42 H86 MOL 1 11.576 17.186 0.219 1.00 0.00
ATOM 43 H88 MOL 1 20.420 13.482 1.898 1.00 0.00
ATOM 44 H90 MOL 1 16.156 17.659 0.209 1.00 0.00
ATOM 45 H92 MOL 1 15.804 16.350 -0.701 1.00 0.00
ATOM 46 H94 MOL 1 15.825 16.231 0.928 1.00 0.00
ATOM 47 H96 MOL 1 21.730 14.802 0.517 1.00 0.00
ATOM 48 H98 MOL 1 20.389 15.020 -0.558 1.00 0.00
END</inlineContents>
</jmolApplet>
</jmol>
|- align="center"
| '''2D Structure'''
| '''3D Structure'''
|}

==== Description ====
White, crystalline alkaloid with a bitter taste.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chemical header}}|
|-align="center" colspan="1" bgcolor="#ffffff" |
|}

{| class="toccolours" border="1" style="float: center; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|- bgcolor = "#ffffff"
! {{chemical header}}| '''Chemical Data'''
|
|-
| [http://www.iupac.org/dhtml_home.html Systematic (IUPAC) name]
| (2-ethenyl-4-azabicyclo[2.2.2]oct-5-yl)
-(6-methoxyquinolin-4-yl)-methanol
|-
| Molecular formula
|C20H24N2O2
|-
| Molecular mass
| 324.417 g/mol
|-
| Melting point
| 177 °C
|-
| [http://www.cas.org/ CAS number]
| 150-95-0
|-
|}

== Uses of Quinine: A Very Brief History ==
[[Image:quinine.jpg|right|100|Antique quinine bottles]]
An extraction from the bark of the Cinchona tree (found mainly in South America) had been used to treat fever since before the 1600s by the Peruvian Indians before European explorers found that it was also an effective treatment for Malaria. During 1820, on it's introduction in Europe as a treatment for Malaria sufferers that quinine, the active compound in the bark, was first isolated and named quinine. The early cure for malaria in Europe was in fact a healthy dose of gin and tonic.

Use and supply of quinine was continued until 1941, when Japan invaded Java (at that point supplier of 95% of the world's Cinchona bark) and prevented its export. Alternative malaria treatments were hastily developed (chloroquine and mefloquine for example) for treatment of soldiers during the war. In 1957 a global campaign was launched using these new drugs aiming to totally eradicate the malaria parasite. However, it was soon realised that the parasite developed a resistance and drugs became less and less effective. Consequently, interest in quinine has risen considerably since with the aim of developing a more effective treatment.

== Quinine and Malaria ==
As a consequence of the ongoing global threat of malaria, research into cures and ways to prevent the disease spreading is also a continuous process. However, as the bacteria gains resistance to man-made drugs, interest is returning to the use of quinine as an effective cure. Around 400 million people suffer from infection every year. Those particularly effected are those in tropical and subtropical regions.
The disease is caused by protozoan parasites of the genus Plasmodium.
The prasite is primarily carried by female mosquitoes of the Anopheles genus. Young mosquitoes first ingest the malaria parasite by feeding on an the blood of previuosly infected humans. The parasite is then carried in the saliva glands, and is passed on during the next meal. The symptoms of malaria are caused when the bacteria attack the red blood cells.

Quinine is an effective treatment still because if affects the way that the bacteria interacts with haemoglobin in the blood.

== Mechanism of Action ==
[[Image:mechofac.gif|left|frame|300|Quinine in action]]

It is understood that the quinine is effective due to the fact that it is toxic to the malaria parasite, specifically by interfering with the parasite's ability to break down and digest hemoglobin. Consequently, the overall effect is to starve the parasite or alternatively cause the build-up of toxic levels of partially degraded hemoglobin in the parasite. Both have the effect of preventing the parasite from causing problems in the haemoglobin.

== Synthesis of Quinine ==
[[Image:quinsynth.gif|right|frame|300|Borrowed from http://www.chm.bris.ac.uk/webprojects2002/jeffrey/chemsynth.htm]]

Although Woodward and Doering are credited with having found the first synthesis of quinine in 1944, they actually refined a method first discovered in 1918 by Paul Rabe. His process was less effective as it did not consider the stereochemistry of the final product, and as a result a racemic mixture of two enatiomers was produced.
It was in 1960 that a chemist named stork analysed the retrosynthesis of quinine and devised a new method of production. However, it can be seen rom the reaction scheme that boh processes are long and complicated. Neither are used to a huge extent comercially, and whenever possible quinine is still extracted from cinchona bark.

== References ==
http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a682322.html

http://www.rxlist.com/cgi/generic3/quinine.htm

http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00563.txt

http://www.patient.co.uk/showdoc/30002116/

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*[[it:Tetrahydrocannabinol|Tetrahydrocannabinol]]
*[[it:Linalool|Linalool(A component of essential oil)]]
*[[it:Dihydroartemisinin| Dihydroartemisinin, An Active Anti-Malarial]]
*[[it:Acrolein|Acrolein]]
*[[it:Cinnamaldehyde|Cinnamaldehyde: The smell and taste in the spice cinnamon]]
*[[it:Melatonin|Melatonin: The All-Natural Nightcap]]
*[[it:Benzylpiperazine|Benzylpiperazine (BZP): Party Pills]]
*[[it:Vanillin|Vanillin, flavouring used in food]]
*[[it:Gingerol|Gingerol, precursor of Zingerone]]
*[[it:MSG|MSG; because everyone loves the flavour]]
*[[it:DDT|DDT, Pesticide]]
*[[it:Oseltamivir|Oseltamivir, neuraminidase inhibitor]]
*[[it:Caffeine|Caffeine]]
*[[it:Fullerene]]
*[[it:Histrionicotoxin]]
*[[it:limonene]]
*[[it:Capsanthin]]
*[[it:Safrole|Safrole: A formerly popular food and drinks additive]]
*[[it:Adenosine_Triphosphate|Adenosine Triphosphate (ATP), Energy source in muscles]]
*[[it:Aspartame|Aspartame: Artificial sweetener]]
*[[it:Astemizole|Astemizole:non-sedating anti-histamine]]
*[[it:Flucloxacillin|Flucloxacillin:antibiotic]]
*[[it:Quinine|Quinine: A natural remedy]]

== [[Special:Export|Export Pages]] ==

This takes you to an '''Export''' page. A backup of the Projects area can be made (in XML) if you want to keep your own ''snapshot'' of the project pages at any instant. After you Export the page you want (ie '''It:projects''' or '''It:Lignocaine''' for example) the XML encoding of it will appear in your browser Window. You should '''view source''' for this material, copy it to a text editor, and thence save it to disk.

== Overlaps ==

If someone else starts editing a page at the same time as you, the system will detect this and offer alternatives for you to deal with. For example, it may suggest you copy the contents of the page you have been editing and merge it into the other person's page,
so that both the sets of edits are preserved. Read the on-screen instructions carefully!

Another precaution you could take is to keep a copy of the contents of the page you are editing in eg Wordpad (or Word),
make the changes there, and then copy the entire lot to the Wiki page to preview and then save. That way, if your contribution
is overlapped by someone else, you will still have a copy, and you can then resubmit it.
----
--[[User:Rzepa|Rzepa]] 12:25, 19 October 2006 (BST)--[[User:Rzepa|Rzepa]] 08:31, 5 November 2006 (UTC)

== Wiki Utillities ==
Utilities have been written to help the conversion of material from HTML.

# [http://diberri.dyndns.org/wikipedia/html2wiki/ A HTML2Wiki Converter]

No wiki2html converter suitable for use has yet been identified.
=== Wiki Templates ===

[[Template:DOI]] and [[Template:Doi-inline]] are providea as (protected) templates for your use. Many other templates exist, often to be found on e.g. Wikipedia pages. You may decide one of these is of particular use, or of interest. If so, you can install it on the wiki here for you and others to use. Add below a line that looks like {{template-name|parameter}}, save, and click on the red text to create the new template. If you prefer the task of adding useful templates to that of adding information about molecules, then you will be given full credit for performing this valuable service for others!
--[[User:Rzepa|Rzepa]] 14:41, 20 October 2006 (BST)

----
[[Template:Chem-Data]]

[[Template:Chembox supplement]] - to be linked to from the supplementary section of the table in the template above, for usage see [[Template_talk:chembox_supplement|here]]

[[Template:NFPA_704]] - for notes on how to use, see [[Template_talk:NFPA_704|here]]

[[R & S Phrases]]

It:projects

2006-11-24T11:33:08Z

Jf205: /* Supplemental Project Page */

__FORCETOC__

'''''You MUST use the Edit buttons on the right to edit this content. Do NOT use the Edit button on the top of this page.'''''
== Sandbox (Play-Pen) ==

This is an area where you can play without worrying what you do. Enter it by pressing the [Edit] button '''on the right''' and '''not''' at the top. Go here for a [http://en.wikipedia.org/wiki/Wikipedia:Cheatsheet ''cheat sheet''] summary of how to create a Wiki page. It's a free-for-all in here! Learn how to use a Wiki by coming here! PS This is how to do Greek: Α, α, β Δ, δ
Try copying/pasting some of the [http://www.ch.ic.ac.uk/local/it/lab1.html examples in the course work] into this page. See the effect by selecting '''Show Preview'''. No not use '''Save Page''' so as to leave this area uncluttered for others.
----

== Main Project Page ==
'''Please do not edit this page itself'''. Click on one of the titles to start editing.
{| summary="CIT Project Titles" border="1"
! bgcolor="cyan" |Project Number
! bgcolor="cyan" |General Keywords
|-
| bgcolor="#CCFF00" |01
| bgcolor="#CCFF00" | [[it:Lignocaine|Lignocaine (used in dentistry as a "local")]]
|-
| bgcolor="#CCFF00" |02
| bgcolor="#66FF99" | [[it:Piperine|Piperine (active ingredient of both black and white pepper)]]
|-
| bgcolor="#CCFF00" |03
| bgcolor="#CCFF00" | [[it:Rapamycin|Rapamycin (prevents transplant rejection)]]
|-
| bgcolor="#CCFF00" |04
| bgcolor="#66FF99" | [[it:Gossypol|Gossypol (male birth control)]]
|-
| bgcolor="#CCFF00" |05
| bgcolor="#CCFF00" | [[it:Gentamycin|Gentamicin A (aminoglycoside antibiotic)]]
|-
| bgcolor="#CCFF00" |06
| bgcolor="#66FF99" | [[it:Herceptin|Herceptin (topical anticancer drug)]]
|-
| bgcolor="#CCFF00" |07
| bgcolor="#CCFF00" | [[it:Gingerone|Zingerone (the characteristic smell of ginger)]]
|-
| bgcolor="#CCFF00" |08
| bgcolor="#66FF99" | [[it:Sucralose|Sucralose (non-metabolizable sweetening agent)]]
|-
| bgcolor="#CCFF00" |09
| bgcolor="#CCFF00" | [[it:Bufotoxin|Bufotoxin (active component of the toad ''Bufo vulgaris'')]]
|-
| bgcolor="#CCFF00" |10
| bgcolor="#66FF99" | [[it:Roaccutane|Roaccutane (treatment for severe acne)]]
|-
| bgcolor="#CCFF00" |11
| bgcolor="#CCFF00" | [[it:Sibutramine|Sibutramine (appetite suppresor)]]
|-
| bgcolor="#CCFF00" |12
| bgcolor="#66FF99" | [[it:Anandamide|Anandamide (the "feel-good" factor in chocolate)]]
|-
| bgcolor="#CCFF00" |13
| bgcolor="#CCFF00" | [[it:h3nbh3|Ammonia-borane: H3N-BH3 (Hydrogen storage molecule?)]]
|-
| bgcolor="#CCFF00" |14
| bgcolor="#66FF99" | [[it:Methoxsalen|Methoxsalen (Treatment of psoriasis)]]
|-
| bgcolor="#CCFF00" |15
| bgcolor="#CCFF00" | [[it:Hycocine|Hyoscine (From Mandrake and Witches Henbane, pre-med before surgery)]]
|-
| bgcolor="#CCFF00" |16
| bgcolor="#66FF99" | [[it:Capreomycin|Capreomycin (Drug-resistant TB)]]
|-
| bgcolor="#CCFF00" |17
| bgcolor="#CCFF00" | [[it:wilkinson|Wilkinson's catalyst]]
|-
| bgcolor="#CCFF00" |18
| bgcolor="#66FF99" | [[it:Jacobsen|Jacobsen's epoxidation catalyst]]
|-
| bgcolor="#CCFF00" |19
| bgcolor="#CCFF00" | [[it:Methylaluminoxane|Methylaluminoxane: MAO - hugely important ethylene polymerisation cocatalyst]]
|-
| bgcolor="#CCFF00" |20
| bgcolor="#66FF99" | [[it:Schwartz|Schwartz reagent for the hydrozirconation of alkenes and alkynes]]
|-
| bgcolor="#CCFF00" |21
| bgcolor="#CCFF00" | [[it:Schrock|Schrock metathesis catalyst]]
|-
| bgcolor="#CCFF00" |22
| bgcolor="#66FF99" | [[it:knots|Molecular-scale knots (nanoscale devices)]]
|-
|bgcolor="#CCFF00" |23
| bgcolor="#CCFF00" | [[it:Vioxx|Vioxx (treatment of osteoarthritis symptoms and pain)]]
|-
| bgcolor="#CCFF00" |24
| bgcolor="#66FF99" | [[it:Sertraline|Sertraline HCl (anti-depression)]]
|-
| bgcolor="#CCFF00" |25
| bgcolor="#CCFF00" | [[it:Ceftriaxone|Ceftriaxone (Gonorrhoea)]]
|-
| bgcolor="#CCFF00" |26
| bgcolor="#66FF99" | [[it:Zithromycin|Zithromycin (anti-infective)]]
|-
| bgcolor="#CCFF00" |27
| bgcolor="#CCFF00" | [[it:Lipitor|Lipitor (Cholesterol reducing agent)]]
|-
| bgcolor="#CCFF00" |28
| bgcolor="#66FF99" | [[it:Cyameluric Acid|Cyameluric acid (Linus Pauling's last idea!)]]
|}

== Supplemental Project Page ==

This area is for people who wish to create their own projects if none of the above appeal to them. Click on the '''Edit''' button to the right to open up an editable page,
then add an entry below as follows

*<nowiki> [[it:name_of_project|Descriptive name of intended project]]</nowiki>
*This will produce the effect: [[it:name_of_project|Descriptive name of intended project]]
----
*[[it:sitagliptin_page|Sitagliptin]]
*[[it:Retinal|Retinal, molecule of sight]]
*[[it:Tamoxifen|Tamoxifen, breast cancer treatment]]
*[[it:Morphine|Morphine, painkiller]]
*[[it:Pelargonidin|Pelargonidin, colouring in nature]]
*[[it:Propanil|Propanil, weedkiller]]
*[[it:Ranitidine|Ranitidine, antiulcerative]]
*[[it:chlorphentermine|chlorphentermine, anorectic]]
*[[it:Serotonin|Serotonin, The 'HAPPY' Drug]]
*[[it:Amphidinolide T1|Amphidinolide T1]]
*[[it:Rosiglitazone|Rosiglitazone, drug that is currently used to treat diabetes.]]
*[[it:Furosemide|Furosemide]]
*[[it:Tryptophan|Tryptophan]]
*[[it:methylpentynol|methylpentynol, tranquilliser.]]
*[[it:Ferrocene|Ferrocene]]
*[[it:Scopolamine|Scopolamine, the (Former) Truth Drug]]
*[[it:Camptothecin|Camptothecin,Anti-cancer agent ]]
*[[it:Salmeterol|Salmeterol, an agonist used to treat asthma]]
*[[it:Psilocin|Psilocin]]
*[[it:Epibatidine|Epibatidine]]
*[[it:Beta Carotene|Beta Carotene]]
*[[it:Thyroxine|Thyroxine, the Thyroid Hormone]]
*[[it:Tetrahydrocannabinol|Tetrahydrocannabinol]]
*[[it:Linalool|Linalool(A component of essential oil)]]
*[[it:Dihydroartemisinin| Dihydroartemisinin, An Active Anti-Malarial]]
*[[it:Acrolein|Acrolein]]
*[[it:Cinnamaldehyde|Cinnamaldehyde: The smell and taste in the spice cinnamon]]
*[[it:Melatonin|Melatonin: The All-Natural Nightcap]]
*[[it:Benzylpiperazine|Benzylpiperazine (BZP): Party Pills]]
*[[it:Vanillin|Vanillin, flavouring used in food]]
*[[it:Gingerol|Gingerol, precursor of Zingerone]]
*[[it:MSG|MSG; because everyone loves the flavour]]
*[[it:DDT|DDT, Pesticide]]
*[[it:Oseltamivir|Oseltamivir, neuraminidase inhibitor]]
*[[it:Caffeine|Caffeine]]
*[[it:Fullerene]]
*[[it:Histrionicotoxin]]
*[[it:limonene]]
*[[it:Capsanthin]]
*[[it:Safrole|Safrole: A formerly popular food and drinks additive]]
*[[it:Adenosine_Triphosphate|Adenosine Triphosphate (ATP), Energy source in muscles]]
*[[it:Aspartame|Aspartame: Artificial sweetener]]
*[[it:Astemizole|Astemizole:non-sedating anti-histamine]]
*[[it:Flucloxacillin|Flucloxacillin:antibiotic]]
*[[it:Furosemide|Furosemide: A powerful diuretic]]

== [[Special:Export|Export Pages]] ==

This takes you to an '''Export''' page. A backup of the Projects area can be made (in XML) if you want to keep your own ''snapshot'' of the project pages at any instant. After you Export the page you want (ie '''It:projects''' or '''It:Lignocaine''' for example) the XML encoding of it will appear in your browser Window. You should '''view source''' for this material, copy it to a text editor, and thence save it to disk.

== Overlaps ==

If someone else starts editing a page at the same time as you, the system will detect this and offer alternatives for you to deal with. For example, it may suggest you copy the contents of the page you have been editing and merge it into the other person's page,
so that both the sets of edits are preserved. Read the on-screen instructions carefully!

Another precaution you could take is to keep a copy of the contents of the page you are editing in eg Wordpad (or Word),
make the changes there, and then copy the entire lot to the Wiki page to preview and then save. That way, if your contribution
is overlapped by someone else, you will still have a copy, and you can then resubmit it.
----
--[[User:Rzepa|Rzepa]] 12:25, 19 October 2006 (BST)--[[User:Rzepa|Rzepa]] 08:31, 5 November 2006 (UTC)

== Wiki Utillities ==
Utilities have been written to help the conversion of material from HTML.

# [http://diberri.dyndns.org/wikipedia/html2wiki/ A HTML2Wiki Converter]

No wiki2html converter suitable for use has yet been identified.
=== Wiki Templates ===

[[Template:DOI]] and [[Template:Doi-inline]] are providea as (protected) templates for your use. Many other templates exist, often to be found on e.g. Wikipedia pages. You may decide one of these is of particular use, or of interest. If so, you can install it on the wiki here for you and others to use. Add below a line that looks like {{template-name|parameter}}, save, and click on the red text to create the new template. If you prefer the task of adding useful templates to that of adding information about molecules, then you will be given full credit for performing this valuable service for others!
--[[User:Rzepa|Rzepa]] 14:41, 20 October 2006 (BST)

----
[[Template:Chem-Data]]

[[Template:Chembox supplement]] - to be linked to from the supplementary section of the table in the template above, for usage see [[Template_talk:chembox_supplement|here]]

[[Template:NFPA_704]] - for notes on how to use, see [[Template_talk:NFPA_704|here]]

[[R & S Phrases]]