ChemWiki - User contributions [en]

It07:Cocaine

2007-11-23T12:42:04Z

Ra506: /* Coca Leaf Infusions */

='''Cocaine'''=
<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Cocaine 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:JCE2005p1583fig3.gif|200px]] 
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| methyl (1R,2R,3S,5S)-3- (benzoyloxy)-8-methyl-8-azabicyclo[3.2.1] octane-2-carboxylate <I know this differs from wikipedia. This is correct according to Merck index.>

|-
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C<sub>17</sub>H<sub>21</sub>NO<sub>4
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 303.353 g/mol
|-
| Appearance
| White powder
|-
| CCDC Class
| Alkaloids
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 50-36-2
|-
! {{chembox header}} | Physical Data
|-
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| 1800 mg/mL (20 °C)
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 195 °C (383 °F)
|-
! {{chembox header}} | Pharmacokinetic data
|-
| Bioavailability
| Oral: 33% Nasal: 19%
|-
! {{chembox header}} | Hazards
|-
| MSDS
| [[http://redpoll.pharmacy.ualberta.ca/drugbank/drugBank/drugFile/msds/APRD00080.html External]
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}

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<inlineContents>HEADER CSD ENTRY COCAIN10
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
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CONECT 2 1 3 15 24
CONECT 3 2 4 19 25
CONECT 4 3 5 26 27
CONECT 5 4 6 18 28
CONECT 6 5 7 29 30
CONECT 7 1 6 31 32
CONECT 8 9 19 20
CONECT 9 8 10 14
CONECT 10 9 11 33
CONECT 11 10 12 34
CONECT 12 11 13 35
CONECT 13 12 14 36
CONECT 14 9 13 37
CONECT 15 2 21 22
CONECT 16 22 38 39 40
CONECT 17 18 41 42 43
CONECT 18 1 5 17
CONECT 19 3 8
CONECT 20 8
CONECT 21 15
CONECT 22 15 16
CONECT 23 1
CONECT 24 2
CONECT 25 3
CONECT 26 4
CONECT 27 4
CONECT 28 5
CONECT 29 6
CONECT 30 6
CONECT 31 7
CONECT 32 7
CONECT 33 10
CONECT 34 11
CONECT 35 12
CONECT 36 13
CONECT 37 14
CONECT 38 16
CONECT 39 16
CONECT 40 16
CONECT 41 17
CONECT 42 17
CONECT 43 17
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[[Image:Cocaine1.gif|thumb|right|200|Cocaine]]
[[Image:Screenftir.JPG|thumb|right|300|Infrared Spectrum of Cocaine]]
[[Image:Screen2.JPG|thumb|right|300|Mass Spectrum of Cocaine]]

=History of Cocaine=
Now cocaine is an integral part of the world economy. The active ingredient (an alkaloid) from the coca plant (erythroxylum) was first isolated by a chemist named Albert Niemann. In 1860 he gave the compound the name cocaine.
The drug induces a sense of exhilaration in the user primarily by blocking the reuptake of the neurotransmitter dopamine in the midbrain.
Soon after it was first synthesized, cocaine was available almost everywhere. Sometimes available in powder form, it was also mixed with various other products like wine and cigarettes. Doctors dispensed cocaine as an antidote to morphine addiction. Unfortunately, some patients made a habit of combining them.
Freud described cocaine as a magical drug. He wrote a song of praise in its honor and practiced extensive self-experimentation. To Sherlock Holmes, cocaine was "so transcendentally stimulating and clarifying to the mind that its secondary action is a matter of small moment".

=Forms of Cocaine=
===Cocaine Hydrochloride===
This is the typical form of cocaine; a white powder salt of cocaine. It is synthesised from the leaves of one of two species of erythroxylon plants -- erythroxylon coca and erythroxylon novogranatense.Coca leaves are firstly pulverized; mixed with an alkaline material, an organic solvent and water, and then shaken. The water and leaves are subsequently discarded. Sulphuric acid is then mixed with the solution to remove residual components. Baking soda is added and the mixture is dried, creating a white, putty-like substance called "coca paste". Coca paste is almost always converted into powder cocaine. This is accomplished by, first, dissolving coca paste in aqueous hydrochloric acid, potassium salt is then added to separate undesired substances from the mixture. The final step is to add ammonia; powder cocaine precipitates out and is subsequently dried.

===Cocaine Freebase===
As the name suggests; this form of cocaine is the base form of cocaine. Freebase is cocaine hydrochloride that has been reverse-engineered back to it's base state, rendering it smokeable. Freebase cocaine is manufactured by dissolving powdered cocaine in a highly basic solution, such as aqueous ammonia, to remove the hydrochloric acid. Upon addition of ether, or other organic solvents, freebase crystallises out.

===Crack Cocaine===
Crack cocaine is, in principle, cocaine freebase that has not been crystallised out of organic solvents. Powdered cocaine hydrochloride is dissolved in a solution of [http://en.wikipedia.org/wiki/Baking_powder baking soda] and water. When this solution is boiled a solid substance precipitates out. This solid substance is removed and allowed to dry, the resulting dried chunks are crack cocaine.

===Coca Leaves===
For centuries, the large Indian population of Peru have chewed coca leaves. They were enjoyed in a similar way to the modern consumption of coffee and caffeinated products, i.e. they afforded a short burst of energy and stamina.A coca leaf typically contains between 0.1 and 0.9 percent cocaine. If chewed in such form, it rarely results in social or medical problems for the user.

=Detection=
The detection of cocaine, and by extension all illegal drugs, has become more important in the past decades. Cocaine is easily detected in the urine of users. The hydrolysis of cocaine in the liver results in the formation of a detectable metabolite, [http://en.wikipedia.org/wiki/Benzoylecgonine benzoylecgonine]. Benzoylecgonine is subsequently excreted with urea after being processed by the liver.[[Image:Benzoylecgonine3D.png|thumb|right|200|Benzoylecgonine]]

=Methods of Ingestion=
===Insufflation===
This form of ingestion, also known as 'snorting', is the most common method of ingestion in the Western World. Instead of being inhaled, the cocaine merely coats the inside of the sinuses and is subsequently absorbed through the [http://en.wikipedia.org/wiki/Mucous_membrane mucus membranes]. Excess cocaine not absorbed is collected in mucus and swallowed. This is referred to as 'the drip' and can be considered pleasant or unpleasant depending on personal preference. Damage to the inside of the nose can result from constant insufflation of cocaine; due to the cocaine constricting blood vessels and stopping blood flow to the area.
Cocaine is firstly divided into 'lines' before insufflation; with 'tooters' being used to aid ingestion. Tooters can take the form of rolled up banknotes, hollowed-out pens, pointed ends of keys, specialized spoons and cut straws.

===Injection===
Drug injection allows for the quickest and highest levels of cocaine into the system. After injection, cocaine reaches the brain in seconds and can cause, to the uninitiated, such an intense rush that the user vomits uncontrollably.
===Smoking===
This form of ingestion can only be achieved with cocaine freebase or crack cocaine. A 'crack pipe' is usually employed for smoking both forms; ranging from discarded fizzy drink cans to deep sockets.
===Coca Leaf Infusions===
The free and legal commercialization of dried coca leaves as "coca tea" has been actively promoted by the governments of Peru and Bolivia for many years as a drink with medicinal powers.
===Chewing/Eating===
Coca Leaves are normally mixed with a highly alkaline substance, such as lime, and chewed in the mouth. The drug being absorbed through the inner membrane of the cheek. The leaves are chewed with lime so as to temporarily neutralise the acidity of the stomach; cocaine is hydrolysed and rendered inactive in the acidic stomach. Chewing with lime allows for further assimilation through the stomach.

2007-11-20T17:20:54Z

Ra506: General Structure of a Schrock Catalsyt

General Structure of a Schrock Catalsyt

2007-11-20T15:42:34Z

Ra506: Mass Spectrum of Cocaine

Mass Spectrum of Cocaine

2007-11-20T14:44:11Z

Ra506: /* '''Cocaine''' */

File:Cocainems.gif

2007-11-20T14:42:21Z

Ra506: Mass Spectrum of Cocaine

Mass Spectrum of Cocaine

File:Cocaineir.gif

2007-11-20T14:42:02Z

Ra506: FTIR of cocaine

FTIR of cocaine

2007-11-19T13:38:20Z

Ra506: /* 3D Rendition of Vioxx */

It07:Vioxx

2007-11-19T13:37:39Z

Ra506: /* 3D Rendition of Vioxx */

== Vioxx ==

== 3D Rendition of Vioxx ==
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COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 11.374 11.374 22.939 90.00 90.00 90.00 P 41 21 2 8
ATOM 1 S1 UNK 0 1 4.020 -4.370 20.122 1.00 0.00
ATOM 2 O1 UNK 0 1 3.975 3.181 17.067 1.00 0.00
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ATOM 5 O4 UNK 0 1 2.704 -4.479 20.687 1.00 0.00
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CONECT 2 13 14
CONECT 3 13
CONECT 4 1
CONECT 5 1
CONECT 6 7 11 23
CONECT 7 6 8 24
CONECT 8 7 9 25
CONECT 9 8 10 26
CONECT 10 9 11 27
CONECT 11 6 10 12
CONECT 12 11 13 15
CONECT 13 2 3 12
CONECT 14 2 15 35 36
CONECT 15 12 14 16
CONECT 16 15 17 21
CONECT 17 16 18 28
CONECT 18 17 19 29
CONECT 19 1 18 20
CONECT 20 19 21 30
CONECT 21 16 20 31
CONECT 22 1 32 33 34
CONECT 23 6
CONECT 24 7
CONECT 25 8
CONECT 26 9
CONECT 27 10
CONECT 28 17
CONECT 29 18
CONECT 30 20
CONECT 31 21
CONECT 32 22
CONECT 33 22
CONECT 34 22
CONECT 35 14
CONECT 36 14
MASTER 0 0 0 0 0 0 0 0 36 0 36 0
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It07:Vioxx

2007-11-19T13:36:22Z

Ra506: New page: == Vioxx == == 3D Rendition of Vioxx == <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> <inlineCo...

== Vioxx ==

== 3D Rendition of Vioxx ==
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COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
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ATOM 35 H13 UNK 0 1 3.384 2.089 18.631 1.00 0.00
ATOM 36 H14 UNK 0 1 2.577 1.777 17.344 1.00 0.00
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CONECT 2 13 14
CONECT 3 13
CONECT 4 1
CONECT 5 1
CONECT 6 7 11 23
CONECT 7 6 8 24
CONECT 8 7 9 25
CONECT 9 8 10 26
CONECT 10 9 11 27
CONECT 11 6 10 12
CONECT 12 11 13 15
CONECT 13 2 3 12
CONECT 14 2 15 35 36
CONECT 15 12 14 16
CONECT 16 15 17 21
CONECT 17 16 18 28
CONECT 18 17 19 29
CONECT 19 1 18 20
CONECT 20 19 21 30
CONECT 21 16 20 31
CONECT 22 1 32 33 34
CONECT 23 6
CONECT 24 7
CONECT 25 8
CONECT 26 9
CONECT 27 10
CONECT 28 17
CONECT 29 18
CONECT 30 20
CONECT 31 21
CONECT 32 22
CONECT 33 22
CONECT 34 22
CONECT 35 14
CONECT 36 14
MASTER 0 0 0 0 0 0 0 0 36 0 36 0
END

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