ChemWiki - User contributions [en]

It:Cocaine

2006-12-08T11:38:05Z

Jk705: /* Uses */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Cocaine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:cocaine structure.bmp]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
title1
title2
43 45 0 0 0 0 0 0 0 0999 V2000
-2.2198 -2.3161 0.6281 N 0 0 0 0 0 0 0 0 0 1
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-0.1399 -0.5349 -0.6491 C 0 0 2 0 0 0 0 0 0 4
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-1.1863 -2.8683 -0.2744 C 0 0 1 0 0 0 0 0 0 6
-3.3057 -3.1895 1.1145 C 0 0 0 0 0 0 0 0 0 7
-2.8864 -1.5497 -1.4560 C 0 0 0 0 0 0 0 0 0 8
-1.9274 -2.7613 -1.6382 C 0 0 0 0 0 0 0 0 0 9
-1.2679 0.6752 1.3467 C 0 0 0 0 0 0 0 0 0 10
-2.0082 1.7286 1.7877 O 0 0 0 0 0 0 0 0 0 11
-3.0344 2.3799 1.1039 C 0 0 0 0 0 0 0 0 0 12
-0.3116 0.3611 2.0570 O 0 0 0 0 0 0 0 0 0 13
0.9608 0.2619 -0.3139 O 0 0 0 0 0 0 0 0 0 14
2.0434 0.5040 -1.0993 C 0 0 0 0 0 0 0 0 0 15
3.0969 1.4166 -0.6178 C 0 0 0 0 0 0 0 0 0 16
4.2546 1.6500 -1.3863 C 0 0 0 0 0 0 0 0 0 17
5.2557 2.5209 -0.9239 C 0 0 0 0 0 0 0 0 0 18
5.1089 3.1688 0.3131 C 0 0 0 0 0 0 0 0 0 19
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-1.7731 0.8477 -0.6932 H 0 0 0 0 0 0 0 0 0 24
0.8420 -2.4515 -0.9398 H 0 0 0 0 0 0 0 0 0 25
0.5542 -2.0526 0.7546 H 0 0 0 0 0 0 0 0 0 26
-0.9673 -3.9096 -0.0361 H 0 0 0 0 0 0 0 0 0 27
-3.7996 -2.7013 1.9569 H 0 0 0 0 0 0 0 0 0 28
-2.8896 -4.1366 1.4611 H 0 0 0 0 0 0 0 0 0 29
-4.0503 -3.3844 0.3476 H 0 0 0 0 0 0 0 0 0 30
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-3.8200 1.6760 0.8305 H 0 0 0 0 0 0 0 0 0 36
-2.6421 2.8604 0.2069 H 0 0 0 0 0 0 0 0 0 37
2.1598 -0.0545 -2.1917 O 0 0 0 0 0 0 0 0 0 38
4.3818 1.1736 -2.3149 H 0 0 0 0 0 0 0 0 0 39
6.1155 2.6878 -1.5048 H 0 0 0 0 0 0 0 0 0 40
5.8571 3.8204 0.6593 H 0 0 0 0 0 0 0 0 0 41
3.8447 3.4267 2.0117 H 0 0 0 0 0 0 0 0 0 42
2.1034 1.9164 1.2136 H 0 0 0 0 0 0 0 0 0 43
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M END</inlineContents>
</jmolApplet>
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|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Systematic Name]]
| colspan="2"| 2beta-carbomethyoxy-3beta-benzoxytropane
|-
| [[Alternative Chemical Names]]
| colspan="3"| [1R-(exo,exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic |acid methyl ester, 3beta-hydroxy-1alphaH, 5alphaH-tropane-2beta-carboxylic acid methyl ester |benzoate, l-cocaine, beta-cocaine, benzoylmethyl-ecgonine, ecgonine methyl ester benzoate
|-
| [[Chemical formula|Molecular formula]]
| colspan="2" | C<sub>17</sub>H<sub>21</sub>NO<sub>4
|-
| [[Molecular Weight]]
| colspan="2" | 303.36
|-
| [[Melting Points]]
| colspan="2" | 98C(monoclinic tablets)/195C(Hydchloride)/58-63C(nitrate dihydrate)
|-
| [[Appearance]]
| colspan="2" | Crystalline, granular or powder
|-
| [[Taste]]
| colspan="2" | Saline, bitter - numbs mouth area
|-
| {{chembox header}} colspan="3"|
|}

Cocaine is made from an alkaloid extracted from the Erythroxylon coca plant - a shrub indigenous to the Andean area of South America. It is also possible to synthesise it in a lab from basic starting materials, but it involves more than a dozen steps and yields prove to be miserably low, hence the reliance upon the coca plant for large scale production.

===Merck Index Entry===

2515. Coca. Erythroxylon; cuca; hayo; ipado. Dried leaves of Erythroxylon coca Lam., Erythroxylaceae. Habit. Bolivia, Brazil, Peru, cultivated in Java. Constit. 0.5-1% alkaloids in the South American, 1.5-2.5% in the Javanese leaves. In the former, the major alkaloid is cocaine; in the latter, there is very little cocaine, the alkaloids, consisting chiefly of ecgonine derivatives such as benzoyl ecgonine, methyl ecgonine, etc. The Java leaves also contain small quantities of tropococaine which is apparently absent in the South American leaves. Other "cocaine" alkaloids present are truxillococaine, isatropylcocaine or cocamine, cocaicine.[http://www.merckindex.com Merck Index]

===Synthetic Route===

[[image:Cocaine Synthetic Route.gif]]

===Uses===

Cocaine is a stimulant, a vasoconstrictor and can be used as a local anaesthetic. The anaesthetic action works by blocking sensory impulses and the effect is maintained by the constriction of blood vessels. It is also useful during operations as it reduces bleeding (because of vasoconstriction).

Cocaine hydrochloride (4 and 10%) solution is used mainly as a topical local anesthetic for the upper respiratory tract. The vasoconstrictor and local anesthetic properties of cocaine cause anesthesia and mucosal shrinkage. It constricts blood vessels and reduces blood flow, and is used to reduce bleeding of the mucous membranes in the oral, laryngeal, and nasal cavities.[http://www.deadiversion.usdoj.gov/drugs_concern/cocaine/cocaine.htm DEA]

Cocaine has been used for centuries in South America as it allows you to work for extended periods of time without experiencing fatigue or hunger. When used to achieve these effects the drug is taken orally, as there isn’t a large effect when administered this way and so little behavioural alterations.

Recreational users usually inhale the drug in powder form (by ‘snorting’). This is the preferred way to take the drug as the effects are felt within a quarter of an hour and can last up to about an hour depending on the quantity and type of cocaine taken. Cocaine is also injected directly into the blood stream which reduces the time it takes for the effect to set in as the cocaine doesn't need to be absorbed. Cocaine can cause the user to feel in a state of ‘euphoria’. This is achieved by the body blocking the dopamine transporter protein, this means when dopamine is released it cannot be taken up again so there is build up of it in the brain.

===Chemistry of Cocaine===

The cocaine that is snorted, injected or otherwise introduced directly into the blood stream is an ester of benzoic acid and Ecgonine, an amino alcohol. This is similar in structure to many other local anaesthetics.

===Crack Cocaine===

Crack cocaine, or simply 'crack' as its known, is the free-base form of cocaine, and is made by preparing an aqueous solution of cocaine hydrochloride and adding ammonia to alkalinize the solution and precipitate the cocaine in its alkaloid form. This form can be smoked, because it vapourises before decomposing, and is popular because of the rapid on effect (3-7 seconds) and more intense sensations. However, these effects last only up to 20 minutes and cause much faster addiction as a result than regular cocaine use.

===Pharmacology of Cocaine===

Once in the blood stream, cocaine has a 'double whammy' effect on the mind. Firstly, it stimulates the release of dopamine and norepinephrine, and then it inhibits their inhibitors, so the feelings, as described by Freud, of "euphoria, a perceived increase in self control, greater work capacity, perceived long-lasting mental or physical work without fatigue, perceived ability to forego food and sleep" - which he later described as the "perfect illusion" - are all caused by a massive excess of these 'happy' chemicals. This is also what causes the depressive 'come down' experienced by users. The body maintains a carefull balance of dopamine and norepinephrine, so when cocaine disrupts the balance, the body immediately attempts to restore order by releasing more and more inhibitors, which cocaine blocks. This means so long as there is cocaine in the blood stream, the user is on a high, however, as soon as the cocaine has been metabolised, a massive excess of inhibitors is released, causing a lack of dopamine and norepinephrine - leading to a depressive state of mind. This is also how addiction is caused. If cocaine is used very regularly, even for a short period of time, the body and mind adapt to functioning under high dopamine concentrations, so when these return to normal, with no cocaine, the user needs to bring them back up to function properly.

The half-life of cocaine in blood plasma is about 90 minutes. It gets metabolised to benzoylecgonine and ecgonine methyl esterby by plasma esterase and liver enzymes, especially cholinesterase, which is crucial to its breakdown, and a tiny number of deaths have been caused by individuals with hereditary cholinesterase deficiency taking cocaine.

===Cocaine and Alcohol===

When there is alcohol and cocaine present in the blood stream, as is usually the case, the two form an even more potent stimulant - cocaethylene, an ethyl homologue of cocaine. Having an almost identical pharmacological profile to cocaine, and almost identical effects, the primary reason for its greater stimulation is its increased half-life - 150 minutes.

=====Cocaine, Cocaethylene and other important Metabolites=====
[[image:cocaethylene.jpg]]
[http://www.forensicmed.co.uk/pharmacology.htm]

===Cocaine, Freud and others===

The first people to use cocaine where the indiginous people of parts of South America, as thats where the coca plant grows naturally. Large amounts of archeological evidence suggests that the drug was initially only used by the upper social classes and religious figures, as it was thought to have mystical powers. However, from the Incan period onwards (1450s) the drug was used by labourers, soldiers and pretty much everyone for its ability to make people work tirelessly and with little food - hence its comical name 'Columbian marching powder'.

At the end of the nineteenth century, the great psychologist and father of psychoanalysis and dream interpretation, Sigmund Freud, was an avid user of the drug, and around this time he wrote most of his theories on dreams and psychoanalysis. Many others around that time, and much later, until its recent outlawing, would've enjoyed cocaine products. Queen Victoria, Winston Churchill and many others could've enjoyed cocaine bubble gum, proper coca-cola, cocaine tootache drops and many others.

===Interesting Cocaine Anekdotes, Myths etc.===

Cocaine is very stable, and binds to the ink in banknotes, so almost all the banknotes in circulation, bar the newest ones, will have traces of cocaine on them, so most people handle cocaine every day!
Most dogs that are used to search for cocaine are turned into addicts first, so they search for the drugs with an increased vigour and efficiency.
The first cocaine cartel was formed, not in Colombia, but in Amsterdam. Founded in 1910, the Cocaine Manufacturers Syndicate included pharmaceutical giants Merck, Sandoz and Hoffman-LaRoche.
Up until the 1980's, the CIA actively supported and funded cocaine cartels and dealers who were willing to help in the fight against communism.
Coca has been used to measure time and distance, when travellers in ancient South America used to describe journeys in terms the number of coca leaves one chews when making it.
Coca-Cola really did contain cocaine

===Dangers===

Cocaine is cardiotoxic. It can cause: ventricular arrhythmia, angina pectoris and myocardial infarction.

It can also cause seizures, delirium, confusion, paranoia, anorexia (as it suppresses hunger), liver toxicity and probably more. Depending on an individuals sensitivity to the drug.

===References===

1. http://www.drugfreesport.com/choices/drugs/street/cocaine.html

2. Wikipedia

3. http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/psychedelicchemistry/chapter8.html

It:Cocaine

2006-12-06T15:32:08Z

Jk705:

It:Cocaine

2006-12-06T15:31:07Z

Jk705:

It:Cocaine

2006-12-06T15:27:18Z

Jk705:

It:Cocaine

2006-12-06T15:26:11Z

Jk705:

It:Cyameluric Acid

2006-12-06T15:18:34Z

Jk705:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D Structure of Cyanmeluric Acid
|-
| align="center" colspan="3" bgcolour="#ffffff" | [[Image:Cyanmeluric Acid jaa05.gif]]
|-
! {{chembox header}} colspan="3" |3D structure of Cyanmeluric Acid<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>
HEADER NONAME 20-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Nov-06 0 NONE 4
ATOM 1 O 0 -1.758 -3.611 0.001 0.00 0.00 O-1
ATOM 2 C 0 -1.166 -2.396 0.001 0.00 0.00 C+0
ATOM 3 N 0 0.161 -2.322 0.000 0.00 0.00 N+0
ATOM 4 C 0 0.766 -1.134 0.000 0.00 0.00 C+0
ATOM 5 N 0 0.000 0.000 0.000 0.00 0.00 N+0
ATOM 6 N 0 2.094 -1.016 -0.000 0.00 0.00 N+0
ATOM 7 C 0 2.658 0.188 -0.000 0.00 0.00 C+0
ATOM 8 O 0 4.006 0.283 -0.000 0.00 0.00 O-1
ATOM 9 N 0 1.930 1.300 -0.000 0.00 0.00 N+0
ATOM 10 C 0 0.599 1.231 0.001 0.00 0.00 C+0
ATOM 11 N 0 -0.167 2.321 -0.000 0.00 0.00 N+0
ATOM 12 C 0 -1.492 2.208 0.001 0.00 0.00 C+0
ATOM 13 O 0 -2.248 3.328 -0.000 0.00 0.00 O-1
ATOM 14 N 0 -2.091 1.021 0.001 0.00 0.00 N+0
ATOM 15 C 0 -1.366 -0.097 0.000 0.00 0.00 C+0
ATOM 16 N 0 -1.927 -1.305 -0.004 0.00 0.00 N+0
CONECT 1 2 0 0 0 NONE 21
CONECT 2 1 16 3 0 NONE 22
CONECT 3 2 4 0 0 NONE 23
CONECT 4 3 5 6 0 NONE 24
CONECT 5 4 10 15 0 NONE 25
CONECT 6 4 7 0 0 NONE 26
CONECT 7 6 8 9 0 NONE 27
CONECT 8 7 0 0 0 NONE 28
CONECT 9 7 10 0 0 NONE 29
CONECT 10 9 5 11 0 NONE 30
CONECT 11 10 12 0 0 NONE 31
CONECT 12 11 13 14 0 NONE 32
CONECT 13 12 0 0 0 NONE 33
CONECT 14 12 15 0 0 NONE 34
CONECT 15 14 5 16 0 NONE 35
CONECT 16 15 2 0 0 NONE 36
END NONE 37
</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | Properties
|-
| colspan="1" |IUPAC Systematic Name
| colspan="2"|
|-
| colspan="1" |Molecular formula
| colspan="2" |C<sub>6</sub>N<sub>7</sub>O<sub>3</sub><sup>3-</sup>
|-
| colspan="1" |SMILES String
| colspan="2" |[O-]C1=NC(N23)=NC([O-])=NC2=NC([O-])=NC3=N1
|-
| colspan="1" |Molecular Mass
| colspan="2" |218.11
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |3842474
|-
| colspan="1" |CAS Registry Number
| colspan="2" |42431-24-3
|-
| Melting Point
| colspan="2" |
|-
|colspan="1" |Boiling point
| colspan="2" |
|-
|colspan="1" |Refractive index
| colspan="2" |

|}

===History===
[[Image:Heptazines.bmp]]

The compound showed above is called tri-s-triazine or 1,3,4,6,7,9,9b-Heptaazaphenalene or cyamelurine, if we change three R group with three amino substituents it is called melem. In Melon the heptazine is polymerized with the tri-s-triazine units linked through an amine (NH) link.

Cyameluric acid is the heptazine derivate with three hydroxyl substituents, it has many possible tautomeric structures. Of the seventeen tautomeric forms, this compound is not a hydroxide but an amide as calculations showed that of the tri-oxo forms was found to be the most stable. The first person to suggest a structure for cyameluric acid was Josef Loschmidt, as far back as 1861. His structure was in fact a meta-cyclophane, but this at a time when cyclic compounds of any type were not widely recognised.

==Discovery of Cyameluric acid==
In 1937 a structure of '''cyameluric acid''', C<sub>6</sub>N<sub>7</sub>(OH)<sub>3</sub>, was proposed by ''Pauling'' and ''Sturdivant''. The structure differed greatly from those of previous scientists. This type of molecule seemed to fascinate Pauling; the last thing he wrote on the chalkboard in his office before his death in 1994 was an azide derivative of cyameluric acid. It has been preserved there to this day by his friends.

In 1850 Henneberg prepared salts of the acid, and in 1933 Professor E. C. Franklin suggested the structure:

[[Image:Franklin.bmp]]

Franklin's research led Pauling and Sturdivant to similar formulations as studied by Franklin; hydromelonic acid is related to cyameluric acid as cyanuric tricyanamide is to cyanuric acid.

The Pauling/Sturdivant structure for cyameluric acid is made up of 3 coplanar rings fused together, with all angles approximately equal to 120°, the structure of the cyamelurate ion is shown in the table on the right. It is a delocalised system, and can be represented in a similar way to ''Kekule's'' structure for benzene, in a conjugated form:

[[Image:Resonance.bmp]]

Infinite structures can be formed in a hydrogen bonding network.

This proposed structure seems to hold the best explanation of properties of cyameluric acid. The resonance forms account for the high stability and the acid strength. This structure also corresponds to the hydrolysis porducts and is therefore the most likely structure. Although there is no report of the crystal structure of cyameluric acid to date.

As cyameluric acid has seventeen tautomers, which is the most stable one? DFT calculations (B3LYP/6-31G*) have been carried out on the these tautomers and find out the C3h trioxo tautomer 258 is the most stable. Some energies and absolute NMR shieldings (GIAO) were calculated for 258 and other tri-s-triazines, including cyamelurine and Pauling mystery molecule.

== Tips==
The heptazine derivate with an azide substituent and two hydroxyl groups is called Linus Pauling's mystery molecule. Two theories attempt to lift the mystery. It is suggested that Pauling failed to solve the double helix structure of DNA before Watson and Crick because he viewed uracil as an amide and not as the tautomeric hydroxy compound. The other theory suggests that Pauling intented to use the compound as a potential spectroscopic label for binding to DNA.

==References==

1. [http://www.arkat-usa.org/ARKIVOC/JOURNAL_CONTENT/manuscripts/2004/EM-917KP%20as%20published%20mainmanuscript.pdf "Theroetical study of cyameluric acid and related compounds"]

2. ''Proceedings of the National Academy of Sciences of the Untied States of America'', Vol. 23, No. 12, pp. 615-620 : '''The Structure of Cyameluric Acid, Hydromelonic Acid, and Related Substance''' - Linus Pauling; J. H. Sturdivant

It:Cocaine

2006-12-06T15:11:31Z

Jk705:

It:Cocaine

2006-12-06T14:48:22Z

Jk705:

It:Cocaine

2006-12-06T14:47:49Z

Jk705:

It:Cocaine

2006-12-06T14:46:46Z

Jk705:

It:Cocaine

2006-12-06T14:08:04Z

Jk705:

It:Cocaine

2006-12-06T14:07:36Z

Jk705:

It:Cocaine

2006-12-06T14:05:52Z

Jk705:

It:Cocaine

2006-12-06T13:57:36Z

Jk705:

It:Cocaine

2006-12-06T12:21:34Z

Jk705:

It:projects

2006-12-06T12:21:10Z

Jk705: /* Supplemental Project Page */

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== 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<br /> 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: H<sub>3</sub>N-BH<sub>3</sub> (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!)]]
|}

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*[[it:Vitamin C|Ascorbic acid: Vitamin C]]
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*[[it:Cocaine|Cocaine]]

it:dichlorodifluromethane

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[[R & S Phrases]]

File:Cocaine.bmp

2006-12-05T12:35:25Z

Jk705:

It:Schrock

2006-11-27T16:17:25Z

Jk705:

==Introduction==
[[Image:Schrock2.jpg|thumb|left|General example, commercially available example<sup>2<sup>]]

'''Richard R. Schrock''' won the 2005 Nobel Prize in Chemistry.

His nobel prize speech can be viewed through the following link:[http://nobelprize.org/nobel_prizes/chemistry/laureates/2005/schrock-lecture.html]

This is an important discovery as the catalysts used before were sensitive to air and moisture, created side reactions and were relatively short-lived.<sup>2</sup> Schrock's discovery of the catalysts using tungsten provided one of the first stable metathesis catalyst.<sup>2<sup>

<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER NONAME 20-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Nov-06 0 NONE 4
ATOM 1 C 0 2.963 -1.542 0.211 0.00 0.00 C+0
ATOM 2 C 0 1.711 -2.418 0.287 0.00 0.00 C+0
ATOM 3 C 0 1.225 -2.737 -1.129 0.00 0.00 C+0
ATOM 4 C 0 2.043 -3.720 1.018 0.00 0.00 C+0
ATOM 5 O 0 0.685 -1.722 0.997 0.00 0.00 O+0
ATOM 6 W 0 0.327 -0.023 -0.017 0.00 0.00 W+0
ATOM 7 N 0 -1.038 0.906 0.803 0.00 0.00 N+0
ATOM 8 C 0 -2.234 0.351 0.930 0.00 0.00 C+0
ATOM 9 C 0 -3.290 1.059 1.560 0.00 0.00 C+0
ATOM 10 C 0 -4.515 0.474 1.682 0.00 0.00 C+0
ATOM 11 C 0 -4.733 -0.808 1.195 0.00 0.00 C+0
ATOM 12 C 0 -3.710 -1.515 0.576 0.00 0.00 C+0
ATOM 13 C 0 -2.475 -0.955 0.432 0.00 0.00 C+0
ATOM 14 O 0 1.989 1.107 -0.037 0.00 0.00 O+0
ATOM 15 C 0 1.961 1.904 1.149 0.00 0.00 C+0
ATOM 16 C 0 1.778 0.998 2.368 0.00 0.00 C+0
ATOM 17 C 0 3.278 2.673 1.277 0.00 0.00 C+0
ATOM 18 C 0 0.798 2.895 1.070 0.00 0.00 C+0
ATOM 19 C 0 -0.176 -0.444 -1.804 0.00 0.00 C+0
ATOM 20 C 0 -0.600 0.653 -2.746 0.00 0.00 C+0
ATOM 21 C 0 -0.395 2.011 -2.072 0.00 0.00 C+0
ATOM 22 C 0 0.243 0.584 -4.021 0.00 0.00 C+0
ATOM 23 C 0 -2.078 0.478 -3.101 0.00 0.00 C+0
ATOM 24 H 0 2.744 -0.644 -0.367 0.00 0.00 H+0
ATOM 25 H 0 3.270 -1.260 1.217 0.00 0.00 H+0
ATOM 26 H 0 3.766 -2.098 -0.272 0.00 0.00 H+0
ATOM 27 H 0 1.773 -3.596 -1.516 0.00 0.00 H+0
ATOM 28 H 0 0.160 -2.967 -1.104 0.00 0.00 H+0
ATOM 29 H 0 1.396 -1.876 -1.774 0.00 0.00 H+0
ATOM 30 H 0 2.389 -3.493 2.026 0.00 0.00 H+0
ATOM 31 H 0 1.151 -4.344 1.072 0.00 0.00 H+0
ATOM 32 H 0 2.826 -4.251 0.476 0.00 0.00 H+0
ATOM 33 H 0 -3.123 2.056 1.940 0.00 0.00 H+0
ATOM 34 H 0 -5.321 1.010 2.162 0.00 0.00 H+0
ATOM 35 H 0 -5.708 -1.261 1.298 0.00 0.00 H+0
ATOM 36 H 0 -3.894 -2.512 0.202 0.00 0.00 H+0
ATOM 37 H 0 -1.681 -1.507 -0.049 0.00 0.00 H+0
ATOM 38 H 0 2.649 0.351 2.473 0.00 0.00 H+0
ATOM 39 H 0 1.670 1.610 3.263 0.00 0.00 H+0
ATOM 40 H 0 0.885 0.387 2.236 0.00 0.00 H+0
ATOM 41 H 0 3.408 3.318 0.409 0.00 0.00 H+0
ATOM 42 H 0 3.257 3.280 2.182 0.00 0.00 H+0
ATOM 43 H 0 4.107 1.967 1.333 0.00 0.00 H+0
ATOM 44 H 0 -0.135 2.378 1.296 0.00 0.00 H+0
ATOM 45 H 0 0.953 3.696 1.793 0.00 0.00 H+0
ATOM 46 H 0 0.746 3.316 0.066 0.00 0.00 H+0
ATOM 47 H 0 -0.158 -1.470 -2.142 0.00 0.00 H+0
ATOM 48 H 0 0.658 2.136 -1.818 0.00 0.00 H+0
ATOM 49 H 0 -0.702 2.805 -2.753 0.00 0.00 H+0
ATOM 50 H 0 -0.996 2.060 -1.163 0.00 0.00 H+0
ATOM 51 H 0 0.032 -0.348 -4.546 0.00 0.00 H+0
ATOM 52 H 0 -0.004 1.428 -4.665 0.00 0.00 H+0
ATOM 53 H 0 1.300 0.623 -3.760 0.00 0.00 H+0
ATOM 54 H 0 -2.678 0.527 -2.192 0.00 0.00 H+0
ATOM 55 H 0 -2.384 1.271 -3.782 0.00 0.00 H+0
ATOM 56 H 0 -2.224 -0.490 -3.581 0.00 0.00 H+0
CONECT 1 2 24 25 26 NONE 61
CONECT 2 1 3 4 5 NONE 62
CONECT 3 2 27 28 29 NONE 63
CONECT 4 2 30 31 32 NONE 64
CONECT 5 2 6 0 0 NONE 65
CONECT 6 5 7 14 19 NONE 66
CONECT 7 6 8 0 0 NONE 67
CONECT 8 7 13 9 0 NONE 68
CONECT 9 8 10 33 0 NONE 69
CONECT 10 9 11 34 0 NONE 70
CONECT 11 10 12 35 0 NONE 71
CONECT 12 11 13 36 0 NONE 72
CONECT 13 12 8 37 0 NONE 73
CONECT 14 6 15 0 0 NONE 74
CONECT 15 14 16 17 18 NONE 75
CONECT 16 15 38 39 40 NONE 76
CONECT 17 15 41 42 43 NONE 77
CONECT 18 15 44 45 46 NONE 78
CONECT 19 6 20 47 0 NONE 79
CONECT 20 19 21 22 23 NONE 80
CONECT 21 20 48 49 50 NONE 81
CONECT 22 20 51 52 53 NONE 82
CONECT 23 20 54 55 56 NONE 83
END</inlineContents>
</jmolApplet>
</jmol>

Reference

1.http://www.rsc.org/chemistryworld/restricted/2005/November/prize.asp

It:Cyameluric Acid

2006-11-22T12:53:56Z

Jk705:

File:Franklin.bmp

2006-11-22T12:50:29Z

Jk705:

It:Cyameluric Acid

2006-11-22T12:49:16Z

Jk705:

File:Resonance.bmp

2006-11-22T12:48:02Z

Jk705:

It:Cyameluric Acid

2006-11-22T09:48:19Z

Jk705: /* History */

It:Cyameluric Acid

2006-11-22T09:47:10Z

Jk705:

It:Cyameluric Acid

2006-11-22T09:44:37Z

Jk705: