ChemWiki - User contributions [en]

It:Caffeine

2006-11-21T11:56:59Z

Sv205:

==Introduction==
Caffeine is one of the most widely used central nervous system stimulant. Caffeine is present in coffee, tea, chocolate, soft drinks (eg. red bull, coca-cola). Its effects (vary from person to person and are affected by the body size, and tolerance) include: reduced drowsiness, improved attention span, and faster blood circulation. When used in large doses and over a long period of time a 'dependancy' may arise, a person may even suffer from withdrawal symptoms if they stop taking it.

==Spectra==
Below are the <sup>13</sup>C NMR and the IR spectra of caffeine
[[Image:Caffeine_NMR1.jpg|thumb|left|200|<sup>13</sup>C NMR]]
[[Image:Caffeine_IR.jpg|thumb|right|200|IR]]

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Caffeine'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Caffeine.gif]]
|-
| [[Chemical name]]
| ''1,3,7-trimethyl-2,6-dioxopurine
|-
| [[CAS nummber]]
| 58-08-2
|-
| [[Chemical formula]]
| {{{formula|C<sub>8</sub>H<sub>10</sub>N<sub>4</sub>O<sub>2</sub>
|-
| [[Molecular mass]]
| {{{mol_mass|194.1926 g/mol
|-
| [[Melting point]]
| 238 °C
|-
| [[Boiling point]]
| 178 °C
|-
| [[Water Solubility]]
| 1-5g/100 ml at 23 C
| 1g/5.5 ml at 88 C
|-
| [[Density]]
| 1.23
|-
| [[Comments]]
| White solid, usually powder or needle-like
| Light sensitive
|-
|}

==Synthesis==
Emil Fischer was the first person to synthesise caffeine, in 1895 however his real objective was to study purines in general. The synthesis of caffeine is not an industrially used process as its extraction from coffee beans or even tea leaves is a much more cost effective process and yields 99.5% pure caffeine. A possible way to synthesis caffeine artificially, from Uracil is shown below. The first step is to methylate the uracil, there are 3 alternate ways in which this can be done the yield however is fairly poor with 10% for method 1, 20% for method 2 and 60% for method 3, the subsequent steps involve nitration, reduction (of the nitro- group), and a ring forming reaction, to form theophylline, and an another methylation to for caffeine.

[[Image:Caffsyn1.jpg|thumb|left|400|Step 1]]
[[Image:Caffsyn2.gif|thumb|left|400|Steps 2-6]]

==Metabolism==

Caffeine is completely absorbed by the stomach and small intestine within 45 minutes of ingestion. After ingestion it is taken to all the tissues in the body and is eliminated by first oreder kinetics.
The half-life of caffeine: the time required for the body to eliminate one-half of the total amount of caffeine consumed at a given time. It varies widely among individuals according to such factors such as age, liver function, pregnancy and the level of enzymes present in the liver needed for caffeine breakdown. In healthy adults, caffeine's half-life is approximately 3-4 hours. In women taking oral contraceptives this is increased to 5-10 hours, and in pregnant women the half-life is approximately 9-11 hours.

Caffeine is matabolised in the liver by the cytochrome P450 oxidase enzyme system, into three metabolic dimethylxanthines.
*Paraxanthine (84%) – Has the effect of increasing lipolysis, leading to elevated glycerol and free fatty acid levels in the blood plasma.
*Theobromine (12%) – Dilates blood vessels and increases urine volume. Theobromine is also the principal alkaloid in cocoa, and therefore chocolate.
*Theophylline (4%) – Relaxes smooth muscles of the bronchi, and is used to treat asthma. The therapeutic dose of theophylline, however, is many times greater than the levels attained from caffeine metabolism.

paraxanthine
<jmol>
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<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Tue Nov 21 11:42:09 GMT Standard Time 2006
ATOM 1 O1 MOL 1 11.959 13.788 0.003 1.00 0.00
ATOM 2 C2 MOL 1 12.065 12.554 0.001 1.00 0.00
ATOM 3 C3 MOL 1 13.350 11.903 0.000 1.00 0.00
ATOM 4 N4 MOL 1 10.933 11.727 -0.001 1.00 0.00
ATOM 5 C5 MOL 1 13.488 10.603 0.000 1.00 0.00
ATOM 6 N6 MOL 1 14.591 12.442 0.000 1.00 0.00
ATOM 7 C7 MOL 1 9.620 12.302 -0.007 1.00 0.00
ATOM 8 C8 MOL 1 11.097 10.308 0.002 1.00 0.00
ATOM 9 N9 MOL 1 12.400 9.739 0.002 1.00 0.00
ATOM 10 N10 MOL 1 14.865 10.274 -0.002 1.00 0.00
ATOM 11 C11 MOL 1 14.914 13.842 0.003 1.00 0.00
ATOM 12 C12 MOL 1 15.524 11.381 -0.002 1.00 0.00
ATOM 13 O13 MOL 1 10.102 9.571 0.003 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>

Theorombine
<jmol>
<jmolApplet>
<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Tue Nov 21 11:49:33 GMT Standard Time 2006
ATOM 1 C1 MOL 1 12.056 15.417 0.008 1.00 0.00
ATOM 2 N2 MOL 1 12.208 13.956 0.001 1.00 0.00
ATOM 3 C3 MOL 1 13.490 13.356 -0.003 1.00 0.00
ATOM 4 C4 MOL 1 11.053 13.083 0.001 1.00 0.00
ATOM 5 C5 MOL 1 13.649 12.058 -0.003 1.00 0.00
ATOM 6 N6 MOL 1 14.753 13.991 -0.007 1.00 0.00
ATOM 7 O7 MOL 1 9.913 13.565 0.003 1.00 0.00
ATOM 8 N8 MOL 1 11.233 11.665 -0.002 1.00 0.00
ATOM 9 C9 MOL 1 12.537 11.123 -0.003 1.00 0.00
ATOM 10 N10 MOL 1 14.981 11.819 -0.001 1.00 0.00
ATOM 11 C11 MOL 1 15.648 13.065 -0.008 1.00 0.00
ATOM 12 O12 MOL 1 12.720 9.898 -0.007 1.00 0.00
ATOM 13 C13 MOL 1 15.617 10.532 0.023 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>

Theophylline
<jmol>
<jmolApplet>
<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Tue Nov 21 11:54:14 GMT Standard Time 2006
ATOM 1 O1 MOL 1 12.035 15.254 0.008 1.00 0.00
ATOM 2 C2 MOL 1 12.096 14.019 0.004 1.00 0.00
ATOM 3 C3 MOL 1 13.363 13.331 0.001 1.00 0.00
ATOM 4 N4 MOL 1 10.934 13.230 -0.001 1.00 0.00
ATOM 5 C5 MOL 1 13.451 12.029 0.001 1.00 0.00
ATOM 6 N6 MOL 1 14.623 13.860 -0.001 1.00 0.00
ATOM 7 C7 MOL 1 9.640 13.849 -0.007 1.00 0.00
ATOM 8 C8 MOL 1 11.052 11.811 -0.000 1.00 0.00
ATOM 9 N9 MOL 1 12.333 11.206 0.003 1.00 0.00
ATOM 10 N10 MOL 1 14.793 11.651 -0.003 1.00 0.00
ATOM 11 C11 MOL 1 15.496 12.729 -0.005 1.00 0.00
ATOM 12 O12 MOL 1 10.037 11.107 -0.004 1.00 0.00
ATOM 13 C13 MOL 1 12.471 9.778 0.008 1.00 0.00
TER</inlineContents>
</jmolApplet>
</jmol>

==Extraction==
The main methods to extract caffeine are:

1. Methylene Chloride/Ethyl Acetate Processing
The raw materials (eg. coffee beans) are softened by steam or hot water, and then methylene chloride or ethyl acetate is added which bonds with the caffeine molecules.

2. CO<sub>2</sub> processing
This method involves 'pressure cooking' the raw ingredients with supercritical carbon dioxide, at a high temperature and pressure, the small CO<sub>2</sub> molecules extract the relatively small caffeine molecules, whilst the larger oils and flavouring compounds remain untouched. This makes this method popular for decaffeination of coffee.

3. Water extraction
Water extraction is similar to the methylene chloride/ ethyl acetate process, however instead of adding chemicals the raw materials are left to soak in hot water for longer, to allow the caffeine to diffuse into the water. The water is then passed through a carbon filter which removes the caffeine in the water, but as with the previous method does not affect the flavourings. The water is then passed back to the raw ingredients to allow reabsorption of these flavours.

==Effects==
Caffeine is used recreationally to help stay awake, while in medicine it is used to reduce headaches, as a cardiac stimulant, and also to increase urine production. The reason that caffeine reduces drownsiness is because it binds to the adenosine receptors of the nervous system (adenosine causes drowsiness), and therefore prevents adenosine from doing so. Caffeine also constricts the vessels for blood flow to the brain, and therefore increases its activity.
This increased activity is percieved by the pituitary gland as a sign of danger or emergency, and it releases adrenaline, which makes the heart beat faster, pupils to dilate, and the liver to release sugars (and therefore energy). Caffeine has also got an effect on dopamine release in the brain, which 'activates the pleasure center' of the brain.

==References==
1. Synthetic communications [0039-7911] Zajac yr:2003 vol:33 iss:19 pg:3291

2. [http://www.howstuffworks.com]

It:Caffeine

2006-11-21T11:52:56Z

Sv205:

==Introduction==
Caffeine is one of the most widely used central nervous system stimulant. Caffeine is present in coffee, tea, chocolate, soft drinks (eg. red bull, coca-cola). Its effects (vary from person to person and are affected by the body size, and tolerance) include: reduced drowsiness, improved attention span, and faster blood circulation. When used in large doses and over a long period of time a 'dependancy' may arise, a person may even suffer from withdrawal symptoms if they stop taking it.

==Spectra==
Below are the <sup>13</sup>C NMR and the IR spectra of caffeine
[[Image:Caffeine_NMR1.jpg|thumb|left|200|<sup>13</sup>C NMR]]
[[Image:Caffeine_IR.jpg|thumb|right|200|IR]]

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Caffeine'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Caffeine.gif]]
|-
| [[Chemical name]]
| ''1,3,7-trimethyl-2,6-dioxopurine
|-
| [[CAS nummber]]
| 58-08-2
|-
| [[Chemical formula]]
| {{{formula|C<sub>8</sub>H<sub>10</sub>N<sub>4</sub>O<sub>2</sub>
|-
| [[Molecular mass]]
| {{{mol_mass|194.1926 g/mol
|-
| [[Melting point]]
| 238 °C
|-
| [[Boiling point]]
| 178 °C
|-
| [[Water Solubility]]
| 1-5g/100 ml at 23 C
| 1g/5.5 ml at 88 C
|-
| [[Density]]
| 1.23
|-
| [[Comments]]
| White solid, usually powder or needle-like
| Light sensitive
|-
|}

==Synthesis==
Emil Fischer was the first person to synthesise caffeine, in 1895 however his real objective was to study purines in general. The synthesis of caffeine is not an industrially used process as its extraction from coffee beans or even tea leaves is a much more cost effective process and yields 99.5% pure caffeine. A possible way to synthesis caffeine artificially, from Uracil is shown below. The first step is to methylate the uracil, there are 3 alternate ways in which this can be done the yield however is fairly poor with 10% for method 1, 20% for method 2 and 60% for method 3, the subsequent steps involve nitration, reduction (of the nitro- group), and a ring forming reaction, to form theophylline, and an another methylation to for caffeine.

[[Image:Caffsyn1.jpg|thumb|left|400|Step 1]]
[[Image:Caffsyn2.gif|thumb|left|400|Steps 2-6]]

==Metabolism==

Caffeine is completely absorbed by the stomach and small intestine within 45 minutes of ingestion. After ingestion it is taken to all the tissues in the body and is eliminated by first oreder kinetics.
The half-life of caffeine: the time required for the body to eliminate one-half of the total amount of caffeine consumed at a given time. It varies widely among individuals according to such factors such as age, liver function, pregnancy and the level of enzymes present in the liver needed for caffeine breakdown. In healthy adults, caffeine's half-life is approximately 3-4 hours. In women taking oral contraceptives this is increased to 5-10 hours, and in pregnant women the half-life is approximately 9-11 hours.

Caffeine is matabolised in the liver by the cytochrome P450 oxidase enzyme system, into three metabolic dimethylxanthines.
*Paraxanthine (84%) – Has the effect of increasing lipolysis, leading to elevated glycerol and free fatty acid levels in the blood plasma.
*Theobromine (12%) – Dilates blood vessels and increases urine volume. Theobromine is also the principal alkaloid in cocoa, and therefore chocolate.
*Theophylline (4%) – Relaxes smooth muscles of the bronchi, and is used to treat asthma. The therapeutic dose of theophylline, however, is many times greater than the levels attained from caffeine metabolism.

paraxanthine
<jmol>
<jmolApplet>
<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Tue Nov 21 11:42:09 GMT Standard Time 2006
ATOM 1 O1 MOL 1 11.959 13.788 0.003 1.00 0.00
ATOM 2 C2 MOL 1 12.065 12.554 0.001 1.00 0.00
ATOM 3 C3 MOL 1 13.350 11.903 0.000 1.00 0.00
ATOM 4 N4 MOL 1 10.933 11.727 -0.001 1.00 0.00
ATOM 5 C5 MOL 1 13.488 10.603 0.000 1.00 0.00
ATOM 6 N6 MOL 1 14.591 12.442 0.000 1.00 0.00
ATOM 7 C7 MOL 1 9.620 12.302 -0.007 1.00 0.00
ATOM 8 C8 MOL 1 11.097 10.308 0.002 1.00 0.00
ATOM 9 N9 MOL 1 12.400 9.739 0.002 1.00 0.00
ATOM 10 N10 MOL 1 14.865 10.274 -0.002 1.00 0.00
ATOM 11 C11 MOL 1 14.914 13.842 0.003 1.00 0.00
ATOM 12 C12 MOL 1 15.524 11.381 -0.002 1.00 0.00
ATOM 13 O13 MOL 1 10.102 9.571 0.003 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>

Theorombine
<jmol>
<jmolApplet>
<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Tue Nov 21 11:49:33 GMT Standard Time 2006
ATOM 1 C1 MOL 1 12.056 15.417 0.008 1.00 0.00
ATOM 2 N2 MOL 1 12.208 13.956 0.001 1.00 0.00
ATOM 3 C3 MOL 1 13.490 13.356 -0.003 1.00 0.00
ATOM 4 C4 MOL 1 11.053 13.083 0.001 1.00 0.00
ATOM 5 C5 MOL 1 13.649 12.058 -0.003 1.00 0.00
ATOM 6 N6 MOL 1 14.753 13.991 -0.007 1.00 0.00
ATOM 7 O7 MOL 1 9.913 13.565 0.003 1.00 0.00
ATOM 8 N8 MOL 1 11.233 11.665 -0.002 1.00 0.00
ATOM 9 C9 MOL 1 12.537 11.123 -0.003 1.00 0.00
ATOM 10 N10 MOL 1 14.981 11.819 -0.001 1.00 0.00
ATOM 11 C11 MOL 1 15.648 13.065 -0.008 1.00 0.00
ATOM 12 O12 MOL 1 12.720 9.898 -0.007 1.00 0.00
ATOM 13 C13 MOL 1 15.617 10.532 0.023 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>

==Extraction==
The main methods to extract caffeine are:

1. Methylene Chloride/Ethyl Acetate Processing
The raw materials (eg. coffee beans) are softened by steam or hot water, and then methylene chloride or ethyl acetate is added which bonds with the caffeine molecules.

2. CO<sub>2</sub> processing
This method involves 'pressure cooking' the raw ingredients with supercritical carbon dioxide, at a high temperature and pressure, the small CO<sub>2</sub> molecules extract the relatively small caffeine molecules, whilst the larger oils and flavouring compounds remain untouched. This makes this method popular for decaffeination of coffee.

3. Water extraction
Water extraction is similar to the methylene chloride/ ethyl acetate process, however instead of adding chemicals the raw materials are left to soak in hot water for longer, to allow the caffeine to diffuse into the water. The water is then passed through a carbon filter which removes the caffeine in the water, but as with the previous method does not affect the flavourings. The water is then passed back to the raw ingredients to allow reabsorption of these flavours.

==Effects==
Caffeine is used recreationally to help stay awake, while in medicine it is used to reduce headaches, as a cardiac stimulant, and also to increase urine production. The reason that caffeine reduces drownsiness is because it binds to the adenosine receptors of the nervous system (adenosine causes drowsiness), and therefore prevents adenosine from doing so. Caffeine also constricts the vessels for blood flow to the brain, and therefore increases its activity.
This increased activity is percieved by the pituitary gland as a sign of danger or emergency, and it releases adrenaline, which makes the heart beat faster, pupils to dilate, and the liver to release sugars (and therefore energy). Caffeine has also got an effect on dopamine release in the brain, which 'activates the pleasure center' of the brain.

==References==
1. Synthetic communications [0039-7911] Zajac yr:2003 vol:33 iss:19 pg:3291

2. [http://www.howstuffworks.com]

It:Caffeine

2006-11-21T11:48:14Z

Sv205:

==Introduction==
Caffeine is one of the most widely used central nervous system stimulant. Caffeine is present in coffee, tea, chocolate, soft drinks (eg. red bull, coca-cola). Its effects (vary from person to person and are affected by the body size, and tolerance) include: reduced drowsiness, improved attention span, and faster blood circulation. When used in large doses and over a long period of time a 'dependancy' may arise, a person may even suffer from withdrawal symptoms if they stop taking it.

==Spectra==
Below are the <sup>13</sup>C NMR and the IR spectra of caffeine
[[Image:Caffeine_NMR1.jpg|thumb|left|200|<sup>13</sup>C NMR]]
[[Image:Caffeine_IR.jpg|thumb|right|200|IR]]

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Caffeine'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Caffeine.gif]]
|-
| [[Chemical name]]
| ''1,3,7-trimethyl-2,6-dioxopurine
|-
| [[CAS nummber]]
| 58-08-2
|-
| [[Chemical formula]]
| {{{formula|C<sub>8</sub>H<sub>10</sub>N<sub>4</sub>O<sub>2</sub>
|-
| [[Molecular mass]]
| {{{mol_mass|194.1926 g/mol
|-
| [[Melting point]]
| 238 °C
|-
| [[Boiling point]]
| 178 °C
|-
| [[Water Solubility]]
| 1-5g/100 ml at 23 C
| 1g/5.5 ml at 88 C
|-
| [[Density]]
| 1.23
|-
| [[Comments]]
| White solid, usually powder or needle-like
| Light sensitive
|-
|}

==Synthesis==
Emil Fischer was the first person to synthesise caffeine, in 1895 however his real objective was to study purines in general. The synthesis of caffeine is not an industrially used process as its extraction from coffee beans or even tea leaves is a much more cost effective process and yields 99.5% pure caffeine. A possible way to synthesis caffeine artificially, from Uracil is shown below. The first step is to methylate the uracil, there are 3 alternate ways in which this can be done the yield however is fairly poor with 10% for method 1, 20% for method 2 and 60% for method 3, the subsequent steps involve nitration, reduction (of the nitro- group), and a ring forming reaction, to form theophylline, and an another methylation to for caffeine.

[[Image:Caffsyn1.jpg|thumb|left|400|Step 1]]
[[Image:Caffsyn2.gif|thumb|left|400|Steps 2-6]]

==Metabolism==

Caffeine is completely absorbed by the stomach and small intestine within 45 minutes of ingestion. After ingestion it is taken to all the tissues in the body and is eliminated by first oreder kinetics.
The half-life of caffeine: the time required for the body to eliminate one-half of the total amount of caffeine consumed at a given time. It varies widely among individuals according to such factors such as age, liver function, pregnancy and the level of enzymes present in the liver needed for caffeine breakdown. In healthy adults, caffeine's half-life is approximately 3-4 hours. In women taking oral contraceptives this is increased to 5-10 hours, and in pregnant women the half-life is approximately 9-11 hours.

Caffeine is matabolised in the liver by the cytochrome P450 oxidase enzyme system, into three metabolic dimethylxanthines.
*Paraxanthine (84%) – Has the effect of increasing lipolysis, leading to elevated glycerol and free fatty acid levels in the blood plasma.
*Theobromine (12%) – Dilates blood vessels and increases urine volume. Theobromine is also the principal alkaloid in cocoa, and therefore chocolate.
*Theophylline (4%) – Relaxes smooth muscles of the bronchi, and is used to treat asthma. The therapeutic dose of theophylline, however, is many times greater than the levels attained from caffeine metabolism.

paraxanthine
<jmol>
<jmolApplet>
<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Tue Nov 21 11:42:09 GMT Standard Time 2006
ATOM 1 O1 MOL 1 11.959 13.788 0.003 1.00 0.00
ATOM 2 C2 MOL 1 12.065 12.554 0.001 1.00 0.00
ATOM 3 C3 MOL 1 13.350 11.903 0.000 1.00 0.00
ATOM 4 N4 MOL 1 10.933 11.727 -0.001 1.00 0.00
ATOM 5 C5 MOL 1 13.488 10.603 0.000 1.00 0.00
ATOM 6 N6 MOL 1 14.591 12.442 0.000 1.00 0.00
ATOM 7 C7 MOL 1 9.620 12.302 -0.007 1.00 0.00
ATOM 8 C8 MOL 1 11.097 10.308 0.002 1.00 0.00
ATOM 9 N9 MOL 1 12.400 9.739 0.002 1.00 0.00
ATOM 10 N10 MOL 1 14.865 10.274 -0.002 1.00 0.00
ATOM 11 C11 MOL 1 14.914 13.842 0.003 1.00 0.00
ATOM 12 C12 MOL 1 15.524 11.381 -0.002 1.00 0.00
ATOM 13 O13 MOL 1 10.102 9.571 0.003 1.00 0.00
TER
</inlineContents>

</jmolApplet>
</jmol>

==Extraction==
The main methods to extract caffeine are:

1. Methylene Chloride/Ethyl Acetate Processing
The raw materials (eg. coffee beans) are softened by steam or hot water, and then methylene chloride or ethyl acetate is added which bonds with the caffeine molecules.

2. CO<sub>2</sub> processing
This method involves 'pressure cooking' the raw ingredients with supercritical carbon dioxide, at a high temperature and pressure, the small CO<sub>2</sub> molecules extract the relatively small caffeine molecules, whilst the larger oils and flavouring compounds remain untouched. This makes this method popular for decaffeination of coffee.

3. Water extraction
Water extraction is similar to the methylene chloride/ ethyl acetate process, however instead of adding chemicals the raw materials are left to soak in hot water for longer, to allow the caffeine to diffuse into the water. The water is then passed through a carbon filter which removes the caffeine in the water, but as with the previous method does not affect the flavourings. The water is then passed back to the raw ingredients to allow reabsorption of these flavours.

==Effects==
Caffeine is used recreationally to help stay awake, while in medicine it is used to reduce headaches, as a cardiac stimulant, and also to increase urine production. The reason that caffeine reduces drownsiness is because it binds to the adenosine receptors of the nervous system (adenosine causes drowsiness), and therefore prevents adenosine from doing so. Caffeine also constricts the vessels for blood flow to the brain, and therefore increases its activity.
This increased activity is percieved by the pituitary gland as a sign of danger or emergency, and it releases adrenaline, which makes the heart beat faster, pupils to dilate, and the liver to release sugars (and therefore energy). Caffeine has also got an effect on dopamine release in the brain, which 'activates the pleasure center' of the brain.

==References==
1. Synthetic communications [0039-7911] Zajac yr:2003 vol:33 iss:19 pg:3291

2. [http://www.howstuffworks.com]

It:Caffeine

2006-11-20T15:09:52Z

Sv205:

It:Fullerene

2006-11-20T14:37:27Z

Sv205:

==Introduction==

The fullerenes were discovered in 1985 by researchers at Rice University, are a family of carbon allotropes named after Buckminster Fuller. They are molecules composed entirely of carbon, in the form of a hollow sphere or tube. Fullerenes are very similar in structure to graphite, which is composed of a sheet of linked hexagonal rings, but they contain pentagonal rings that prevent the sheet from being planar.

It:Morphine

2006-10-27T13:48:38Z

Sv205: /* References and External Links */

==Introduction to Morphine==

{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.

|colspan="5"|[[Image:poppy2.GIF]]
|-
|}

==Structure of Morphine==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|
<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|[[Image:200px-Morphine-2D-skeletal.GIF]]
|-
|}

== Properties of Morphine ==

{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data'''
|-
| IUPAC Name
| align="center"|7,8-didehydro-
4,5-epoxy-17-methylmorphinan-3,6-diol
|-
| Chemical formula
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub>
|-
| Molar Mass
| align="center"|285.4 g/mol
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''
|-
| Bioavailability
| align="center"|... ~30%
|-
| Protein binding
| align="center"|... 30–40%
|-
| Metabolism
| align="center"|... Hepatic 90%
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''
|-
| Pregnancy cat.
| align="center"| C(AU) C(US)
|-
| Legal status
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only
|-
| Dependence Liability
| align="center"| Extremely High
|-
| Routes
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV
|-
|}

==Uses==

Morphine is used legally:

*analgesic in hospital settings for
*Pain after surgery
*Pain associated with trauma
*In the relief of severe chronic pain
*Cancer pain
*Pain from kidney stones
*Back pain
*In epidural anesthesia
*As an antitussive for severe cough
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS)
*To relieve breathlessness in patients in respiratory failure

==Pharmacology of Morphine==

Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.

{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|align="left" colspan="3" bgcolor="white"|
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 11:48:06 GMT Standard Time 2006
ATOM 1 O1 MOL 1 18.255 13.156 0.573 1.00 0.00
ATOM 2 C2 MOL 1 17.569 14.167 -0.163 1.00 0.00
ATOM 3 C3 MOL 1 16.417 14.732 0.663 1.00 0.00
ATOM 4 C4 MOL 1 18.496 15.366 -0.471 1.00 0.00
ATOM 5 C5 MOL 1 17.015 13.567 -1.482 1.00 0.00
ATOM 6 C6 MOL 1 15.693 15.779 0.018 1.00 0.00
ATOM 7 C7 MOL 1 15.307 13.777 1.020 1.00 0.00
ATOM 8 C8 MOL 1 16.942 15.313 2.010 1.00 0.00
ATOM 9 C9 MOL 1 17.646 16.451 -1.361 1.00 0.00
ATOM 10 N10 MOL 1 19.019 15.899 0.861 1.00 0.00
ATOM 11 C11 MOL 1 15.959 12.473 -1.196 1.00 0.00
ATOM 12 C12 MOL 1 14.403 15.799 0.518 1.00 0.00
ATOM 13 C13 MOL 1 16.179 16.645 -0.862 1.00 0.00
ATOM 14 O14 MOL 1 14.159 14.689 1.403 1.00 0.00
ATOM 15 C15 MOL 1 14.899 12.986 -0.210 1.00 0.00
ATOM 16 C16 MOL 1 17.969 16.420 1.747 1.00 0.00
ATOM 17 C17 MOL 1 20.056 16.927 0.663 1.00 0.00
ATOM 18 C18 MOL 1 13.566 16.775 0.184 1.00 0.00
ATOM 19 C19 MOL 1 15.281 17.721 -1.321 1.00 0.00
ATOM 20 O20 MOL 1 13.720 12.646 -0.346 1.00 0.00
ATOM 21 C21 MOL 1 21.259 16.286 0.008 1.00 0.00
ATOM 22 O22 MOL 1 12.278 16.816 0.702 1.00 0.00
ATOM 23 C23 MOL 1 14.040 17.798 -0.803 1.00 0.00
ATOM 24 C24 MOL 1 22.410 16.944 -0.094 1.00 0.00
ATOM 25 H25 MOL 1 19.357 15.031 -1.060 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 11:49:10 GMT Standard Time 2006
ATOM 1 O1 MOL 1 17.558 13.998 -0.496 1.00 0.00
ATOM 2 C2 MOL 1 17.076 15.115 0.248 1.00 0.00
ATOM 3 C3 MOL 1 17.258 16.394 -0.557 1.00 0.00
ATOM 4 C4 MOL 1 15.561 15.011 0.531 1.00 0.00
ATOM 5 C5 MOL 1 17.860 15.228 1.589 1.00 0.00
ATOM 6 C6 MOL 1 16.778 17.574 0.073 1.00 0.00
ATOM 7 C7 MOL 1 18.653 16.799 -0.879 1.00 0.00
ATOM 8 C8 MOL 1 16.508 16.294 -1.921 1.00 0.00
ATOM 9 C9 MOL 1 15.127 16.315 1.434 1.00 0.00
ATOM 10 N10 MOL 1 14.843 14.899 -0.812 1.00 0.00
ATOM 11 C11 MOL 1 19.354 15.543 1.336 1.00 0.00
ATOM 12 C12 MOL 1 17.493 18.660 -0.426 1.00 0.00
ATOM 13 C13 MOL 1 15.791 17.648 0.954 1.00 0.00
ATOM 14 O14 MOL 1 18.548 18.231 -1.333 1.00 0.00
ATOM 15 C15 MOL 1 19.467 16.754 0.400 1.00 0.00
ATOM 16 C16 MOL 1 15.014 16.064 -1.686 1.00 0.00
ATOM 17 C17 MOL 1 13.406 14.609 -0.651 1.00 0.00
ATOM 18 C18 MOL 1 17.129 19.900 -0.114 1.00 0.00
ATOM 19 C19 MOL 1 15.387 18.995 1.400 1.00 0.00
ATOM 20 O20 MOL 1 20.317 17.624 0.613 1.00 0.00
ATOM 21 C21 MOL 1 13.178 13.073 -0.836 1.00 0.00
ATOM 22 O22 MOL 1 17.801 20.995 -0.638 1.00 0.00
ATOM 23 C23 MOL 1 16.014 20.069 0.881 1.00 0.00
ATOM 24 C24 MOL 1 11.870 12.702 -0.129 1.00 0.00
ATOM 25 C25 MOL 1 13.234 12.318 0.500 1.00 0.00
ATOM 26 H26 MOL 1 19.132 16.101 -1.579 1.00 0.00
ATOM 27 H27 MOL 1 15.339 14.101 1.101 1.00 0.00
TER</inlineContents>
</jmolApplet>
</jmol>
|-
|align="left" colspan="3" bgcolor="white"|Naloxone
|Naltrexone
|-
|}

Both naloxone and naltrexone are competitive antagonists at the μ- and κ-opioid receptors, and to a lesser extent at δ-opioid receptors. The blockade of these receptors is what prevents the opiods such as morphine, from combining with these receptor sites thus preventing the side effects usually caused by morphine.

==Derrivatives of Morphine==

Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:
<br>
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]
|[[Image:codeine.gif]]
|[[Image:heroin.gif]]
|-
|align="left" colspan="3" bgcolor="white"|Morphine
|Codeine
|Heroin
|-
|align="left" colspan="3" bgcolor="white"|
|
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>
REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 14:36:05 GMT Standard Time 2006
ATOM 1 O1 MOL 1 12.755 17.484 0.278 1.00 0.00
ATOM 2 C2 MOL 1 14.165 17.279 0.259 1.00 0.00
ATOM 3 C3 MOL 1 14.598 16.294 -0.907 1.00 0.00
ATOM 4 C4 MOL 1 14.783 17.091 1.590 1.00 0.00
ATOM 5 C5 MOL 1 16.085 15.955 -0.655 1.00 0.00
ATOM 6 O6 MOL 1 13.944 14.927 -0.976 1.00 0.00
ATOM 7 C7 MOL 1 16.137 17.074 1.556 1.00 0.00
ATOM 8 C8 MOL 1 15.986 14.685 0.099 1.00 0.00
ATOM 9 C9 MOL 1 16.902 16.950 0.154 1.00 0.00
ATOM 10 C10 MOL 1 16.709 15.628 -2.040 1.00 0.00
ATOM 11 C11 MOL 1 14.759 14.077 -0.164 1.00 0.00
ATOM 12 C12 MOL 1 16.917 14.157 0.888 1.00 0.00
ATOM 13 C13 MOL 1 18.319 16.318 0.340 1.00 0.00
ATOM 14 C14 MOL 1 18.152 15.134 -1.868 1.00 0.00
ATOM 15 C15 MOL 1 14.483 12.853 0.325 1.00 0.00
ATOM 16 C16 MOL 1 18.177 14.972 1.210 1.00 0.00
ATOM 17 C17 MOL 1 16.666 12.844 1.470 1.00 0.00
ATOM 18 N18 MOL 1 18.922 16.087 -1.029 1.00 0.00
ATOM 19 O19 MOL 1 13.263 12.126 0.120 1.00 0.00
ATOM 20 C20 MOL 1 15.521 12.211 1.182 1.00 0.00
ATOM 21 C21 MOL 1 20.289 15.567 -0.871 1.00 0.00
ATOM 22 C22 MOL 1 12.251 12.761 -0.671 1.00 0.00
ATOM 23 H23 MOL 1 16.955 17.909 -0.379 1.00 0.00
ATOM 24 H24 MOL 1 14.357 16.925 -1.773 1.00 0.00
ATOM 25 H25 MOL 1 18.981 17.000 0.892 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>
REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 14:36:49 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.380 10.913 -0.058 1.00 0.00
ATOM 2 C2 MOL 1 22.712 10.864 -0.568 1.00 0.00
ATOM 3 C3 MOL 1 20.932 12.266 -0.071 1.00 0.00
ATOM 4 C4 MOL 1 23.445 9.558 -0.647 1.00 0.00
ATOM 5 O5 MOL 1 23.307 11.901 -0.901 1.00 0.00
ATOM 6 C6 MOL 1 19.783 12.581 0.994 1.00 0.00
ATOM 7 C7 MOL 1 20.757 12.864 -1.427 1.00 0.00
ATOM 8 C8 MOL 1 19.419 14.067 0.744 1.00 0.00
ATOM 9 O9 MOL 1 18.395 11.892 1.004 1.00 0.00
ATOM 10 C10 MOL 1 20.623 14.207 -1.407 1.00 0.00
ATOM 11 C11 MOL 1 18.168 13.977 -0.025 1.00 0.00
ATOM 12 C12 MOL 1 20.420 14.937 -0.012 1.00 0.00
ATOM 13 C13 MOL 1 19.051 14.641 2.138 1.00 0.00
ATOM 14 C14 MOL 1 17.546 12.770 0.237 1.00 0.00
ATOM 15 C15 MOL 1 17.644 14.930 -0.793 1.00 0.00
ATOM 16 C16 MOL 1 19.772 16.333 -0.179 1.00 0.00
ATOM 17 C17 MOL 1 18.538 16.078 2.002 1.00 0.00
ATOM 18 C18 MOL 1 16.298 12.542 -0.183 1.00 0.00
ATOM 19 C19 MOL 1 18.462 16.189 -1.090 1.00 0.00
ATOM 20 C20 MOL 1 16.318 14.720 -1.345 1.00 0.00
ATOM 21 N21 MOL 1 19.493 16.889 1.202 1.00 0.00
ATOM 22 O22 MOL 1 15.642 11.319 0.166 1.00 0.00
ATOM 23 C23 MOL 1 15.656 13.605 -1.022 1.00 0.00
ATOM 24 C24 MOL 1 18.950 18.247 1.075 1.00 0.00
ATOM 25 C25 MOL 1 14.263 11.150 -0.231 1.00 0.00
ATOM 26 C26 MOL 1 13.567 9.867 0.115 1.00 0.00
ATOM 27 O27 MOL 1 13.607 12.019 -0.820 1.00 0.00
ATOM 28 H28 MOL 1 21.358 14.995 0.556 1.00 0.00
ATOM 29 H29 MOL 1 20.362 12.366 1.900 1.00 0.00
ATOM 30 H30 MOL 1 20.458 17.021 -0.692 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|-
|}
<br>
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br>
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br>
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.

<br>

==Contraindications==

*Acute Respiratory Depression
*Acute Alcoholism
*Acute pancreatitis (this may be a result of morphine use as well)
*Renal failure (due to accumulation of the metabolite morphine-6-glucuronide)

==Synthesis of Codeine from Morphine==

[[Image:codeine_s.gif|thumb|Synthesis of Codeine]]

==References and External Links==
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine
*Morphine, Molecule of the Month
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]
*Schmitz J, Stotts A, Rhoades H, Grabowski J. "Naltrexone and relapse prevention treatment for cocaine-dependent patients.". Addict Behav 26 (2): 167-80. PMID 11316375.
*Chicago Recovery Alliance's naloxone distrobution project
*Synthesis of codeine from morphine. Ai, Lin; Chen, Xiaoyuan; Zhang, Le. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005)

It:Morphine

2006-10-27T13:48:17Z

Sv205: /* Synthesis of Codeine from Morphine */

It:Morphine

2006-10-27T13:47:01Z

Sv205:

==Introduction to Morphine==

{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.

|colspan="5"|[[Image:poppy2.GIF]]
|-
|}

==Structure of Morphine==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|
<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|[[Image:200px-Morphine-2D-skeletal.GIF]]
|-
|}

== Properties of Morphine ==

{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data'''
|-
| IUPAC Name
| align="center"|7,8-didehydro-
4,5-epoxy-17-methylmorphinan-3,6-diol
|-
| Chemical formula
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub>
|-
| Molar Mass
| align="center"|285.4 g/mol
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''
|-
| Bioavailability
| align="center"|... ~30%
|-
| Protein binding
| align="center"|... 30–40%
|-
| Metabolism
| align="center"|... Hepatic 90%
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''
|-
| Pregnancy cat.
| align="center"| C(AU) C(US)
|-
| Legal status
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only
|-
| Dependence Liability
| align="center"| Extremely High
|-
| Routes
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV
|-
|}

==Uses==

Morphine is used legally:

*analgesic in hospital settings for
*Pain after surgery
*Pain associated with trauma
*In the relief of severe chronic pain
*Cancer pain
*Pain from kidney stones
*Back pain
*In epidural anesthesia
*As an antitussive for severe cough
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS)
*To relieve breathlessness in patients in respiratory failure

==Pharmacology of Morphine==

Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.

{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|align="left" colspan="3" bgcolor="white"|
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 11:48:06 GMT Standard Time 2006
ATOM 1 O1 MOL 1 18.255 13.156 0.573 1.00 0.00
ATOM 2 C2 MOL 1 17.569 14.167 -0.163 1.00 0.00
ATOM 3 C3 MOL 1 16.417 14.732 0.663 1.00 0.00
ATOM 4 C4 MOL 1 18.496 15.366 -0.471 1.00 0.00
ATOM 5 C5 MOL 1 17.015 13.567 -1.482 1.00 0.00
ATOM 6 C6 MOL 1 15.693 15.779 0.018 1.00 0.00
ATOM 7 C7 MOL 1 15.307 13.777 1.020 1.00 0.00
ATOM 8 C8 MOL 1 16.942 15.313 2.010 1.00 0.00
ATOM 9 C9 MOL 1 17.646 16.451 -1.361 1.00 0.00
ATOM 10 N10 MOL 1 19.019 15.899 0.861 1.00 0.00
ATOM 11 C11 MOL 1 15.959 12.473 -1.196 1.00 0.00
ATOM 12 C12 MOL 1 14.403 15.799 0.518 1.00 0.00
ATOM 13 C13 MOL 1 16.179 16.645 -0.862 1.00 0.00
ATOM 14 O14 MOL 1 14.159 14.689 1.403 1.00 0.00
ATOM 15 C15 MOL 1 14.899 12.986 -0.210 1.00 0.00
ATOM 16 C16 MOL 1 17.969 16.420 1.747 1.00 0.00
ATOM 17 C17 MOL 1 20.056 16.927 0.663 1.00 0.00
ATOM 18 C18 MOL 1 13.566 16.775 0.184 1.00 0.00
ATOM 19 C19 MOL 1 15.281 17.721 -1.321 1.00 0.00
ATOM 20 O20 MOL 1 13.720 12.646 -0.346 1.00 0.00
ATOM 21 C21 MOL 1 21.259 16.286 0.008 1.00 0.00
ATOM 22 O22 MOL 1 12.278 16.816 0.702 1.00 0.00
ATOM 23 C23 MOL 1 14.040 17.798 -0.803 1.00 0.00
ATOM 24 C24 MOL 1 22.410 16.944 -0.094 1.00 0.00
ATOM 25 H25 MOL 1 19.357 15.031 -1.060 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 11:49:10 GMT Standard Time 2006
ATOM 1 O1 MOL 1 17.558 13.998 -0.496 1.00 0.00
ATOM 2 C2 MOL 1 17.076 15.115 0.248 1.00 0.00
ATOM 3 C3 MOL 1 17.258 16.394 -0.557 1.00 0.00
ATOM 4 C4 MOL 1 15.561 15.011 0.531 1.00 0.00
ATOM 5 C5 MOL 1 17.860 15.228 1.589 1.00 0.00
ATOM 6 C6 MOL 1 16.778 17.574 0.073 1.00 0.00
ATOM 7 C7 MOL 1 18.653 16.799 -0.879 1.00 0.00
ATOM 8 C8 MOL 1 16.508 16.294 -1.921 1.00 0.00
ATOM 9 C9 MOL 1 15.127 16.315 1.434 1.00 0.00
ATOM 10 N10 MOL 1 14.843 14.899 -0.812 1.00 0.00
ATOM 11 C11 MOL 1 19.354 15.543 1.336 1.00 0.00
ATOM 12 C12 MOL 1 17.493 18.660 -0.426 1.00 0.00
ATOM 13 C13 MOL 1 15.791 17.648 0.954 1.00 0.00
ATOM 14 O14 MOL 1 18.548 18.231 -1.333 1.00 0.00
ATOM 15 C15 MOL 1 19.467 16.754 0.400 1.00 0.00
ATOM 16 C16 MOL 1 15.014 16.064 -1.686 1.00 0.00
ATOM 17 C17 MOL 1 13.406 14.609 -0.651 1.00 0.00
ATOM 18 C18 MOL 1 17.129 19.900 -0.114 1.00 0.00
ATOM 19 C19 MOL 1 15.387 18.995 1.400 1.00 0.00
ATOM 20 O20 MOL 1 20.317 17.624 0.613 1.00 0.00
ATOM 21 C21 MOL 1 13.178 13.073 -0.836 1.00 0.00
ATOM 22 O22 MOL 1 17.801 20.995 -0.638 1.00 0.00
ATOM 23 C23 MOL 1 16.014 20.069 0.881 1.00 0.00
ATOM 24 C24 MOL 1 11.870 12.702 -0.129 1.00 0.00
ATOM 25 C25 MOL 1 13.234 12.318 0.500 1.00 0.00
ATOM 26 H26 MOL 1 19.132 16.101 -1.579 1.00 0.00
ATOM 27 H27 MOL 1 15.339 14.101 1.101 1.00 0.00
TER</inlineContents>
</jmolApplet>
</jmol>
|-
|align="left" colspan="3" bgcolor="white"|Naloxone
|Naltrexone
|-
|}

Both naloxone and naltrexone are competitive antagonists at the μ- and κ-opioid receptors, and to a lesser extent at δ-opioid receptors. The blockade of these receptors is what prevents the opiods such as morphine, from combining with these receptor sites thus preventing the side effects usually caused by morphine.

==Derrivatives of Morphine==

Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:
<br>
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]
|[[Image:codeine.gif]]
|[[Image:heroin.gif]]
|-
|align="left" colspan="3" bgcolor="white"|Morphine
|Codeine
|Heroin
|-
|align="left" colspan="3" bgcolor="white"|
|
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>
REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 14:36:05 GMT Standard Time 2006
ATOM 1 O1 MOL 1 12.755 17.484 0.278 1.00 0.00
ATOM 2 C2 MOL 1 14.165 17.279 0.259 1.00 0.00
ATOM 3 C3 MOL 1 14.598 16.294 -0.907 1.00 0.00
ATOM 4 C4 MOL 1 14.783 17.091 1.590 1.00 0.00
ATOM 5 C5 MOL 1 16.085 15.955 -0.655 1.00 0.00
ATOM 6 O6 MOL 1 13.944 14.927 -0.976 1.00 0.00
ATOM 7 C7 MOL 1 16.137 17.074 1.556 1.00 0.00
ATOM 8 C8 MOL 1 15.986 14.685 0.099 1.00 0.00
ATOM 9 C9 MOL 1 16.902 16.950 0.154 1.00 0.00
ATOM 10 C10 MOL 1 16.709 15.628 -2.040 1.00 0.00
ATOM 11 C11 MOL 1 14.759 14.077 -0.164 1.00 0.00
ATOM 12 C12 MOL 1 16.917 14.157 0.888 1.00 0.00
ATOM 13 C13 MOL 1 18.319 16.318 0.340 1.00 0.00
ATOM 14 C14 MOL 1 18.152 15.134 -1.868 1.00 0.00
ATOM 15 C15 MOL 1 14.483 12.853 0.325 1.00 0.00
ATOM 16 C16 MOL 1 18.177 14.972 1.210 1.00 0.00
ATOM 17 C17 MOL 1 16.666 12.844 1.470 1.00 0.00
ATOM 18 N18 MOL 1 18.922 16.087 -1.029 1.00 0.00
ATOM 19 O19 MOL 1 13.263 12.126 0.120 1.00 0.00
ATOM 20 C20 MOL 1 15.521 12.211 1.182 1.00 0.00
ATOM 21 C21 MOL 1 20.289 15.567 -0.871 1.00 0.00
ATOM 22 C22 MOL 1 12.251 12.761 -0.671 1.00 0.00
ATOM 23 H23 MOL 1 16.955 17.909 -0.379 1.00 0.00
ATOM 24 H24 MOL 1 14.357 16.925 -1.773 1.00 0.00
ATOM 25 H25 MOL 1 18.981 17.000 0.892 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>
REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 14:36:49 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.380 10.913 -0.058 1.00 0.00
ATOM 2 C2 MOL 1 22.712 10.864 -0.568 1.00 0.00
ATOM 3 C3 MOL 1 20.932 12.266 -0.071 1.00 0.00
ATOM 4 C4 MOL 1 23.445 9.558 -0.647 1.00 0.00
ATOM 5 O5 MOL 1 23.307 11.901 -0.901 1.00 0.00
ATOM 6 C6 MOL 1 19.783 12.581 0.994 1.00 0.00
ATOM 7 C7 MOL 1 20.757 12.864 -1.427 1.00 0.00
ATOM 8 C8 MOL 1 19.419 14.067 0.744 1.00 0.00
ATOM 9 O9 MOL 1 18.395 11.892 1.004 1.00 0.00
ATOM 10 C10 MOL 1 20.623 14.207 -1.407 1.00 0.00
ATOM 11 C11 MOL 1 18.168 13.977 -0.025 1.00 0.00
ATOM 12 C12 MOL 1 20.420 14.937 -0.012 1.00 0.00
ATOM 13 C13 MOL 1 19.051 14.641 2.138 1.00 0.00
ATOM 14 C14 MOL 1 17.546 12.770 0.237 1.00 0.00
ATOM 15 C15 MOL 1 17.644 14.930 -0.793 1.00 0.00
ATOM 16 C16 MOL 1 19.772 16.333 -0.179 1.00 0.00
ATOM 17 C17 MOL 1 18.538 16.078 2.002 1.00 0.00
ATOM 18 C18 MOL 1 16.298 12.542 -0.183 1.00 0.00
ATOM 19 C19 MOL 1 18.462 16.189 -1.090 1.00 0.00
ATOM 20 C20 MOL 1 16.318 14.720 -1.345 1.00 0.00
ATOM 21 N21 MOL 1 19.493 16.889 1.202 1.00 0.00
ATOM 22 O22 MOL 1 15.642 11.319 0.166 1.00 0.00
ATOM 23 C23 MOL 1 15.656 13.605 -1.022 1.00 0.00
ATOM 24 C24 MOL 1 18.950 18.247 1.075 1.00 0.00
ATOM 25 C25 MOL 1 14.263 11.150 -0.231 1.00 0.00
ATOM 26 C26 MOL 1 13.567 9.867 0.115 1.00 0.00
ATOM 27 O27 MOL 1 13.607 12.019 -0.820 1.00 0.00
ATOM 28 H28 MOL 1 21.358 14.995 0.556 1.00 0.00
ATOM 29 H29 MOL 1 20.362 12.366 1.900 1.00 0.00
ATOM 30 H30 MOL 1 20.458 17.021 -0.692 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|-
|}
<br>
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br>
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br>
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.

<br>

==Contraindications==

*Acute Respiratory Depression
*Acute Alcoholism
*Acute pancreatitis (this may be a result of morphine use as well)
*Renal failure (due to accumulation of the metabolite morphine-6-glucuronide)

==Synthesis of Codeine from Morphine==
[[Image:codeine_s.gif|thumb|Synthesis of Codeine]]

==References and External Links==
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine
*Morphine, Molecule of the Month
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]
*Schmitz J, Stotts A, Rhoades H, Grabowski J. "Naltrexone and relapse prevention treatment for cocaine-dependent patients.". Addict Behav 26 (2): 167-80. PMID 11316375.
*Chicago Recovery Alliance's naloxone distrobution project
*Synthesis of codeine from morphine. Ai, Lin; Chen, Xiaoyuan; Zhang, Le. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005)

It:Morphine

2006-10-27T13:43:40Z

Sv205:

==Introduction to Morphine==

{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.

|colspan="5"|[[Image:poppy2.GIF]]
|-
|}

==Structure of Morphine==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|
<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|[[Image:200px-Morphine-2D-skeletal.GIF]]
|-
|}

== Properties of Morphine ==

{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data'''
|-
| IUPAC Name
| align="center"|7,8-didehydro-
4,5-epoxy-17-methylmorphinan-3,6-diol
|-
| Chemical formula
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub>
|-
| Molar Mass
| align="center"|285.4 g/mol
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''
|-
| Bioavailability
| align="center"|... ~30%
|-
| Protein binding
| align="center"|... 30–40%
|-
| Metabolism
| align="center"|... Hepatic 90%
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''
|-
| Pregnancy cat.
| align="center"| C(AU) C(US)
|-
| Legal status
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only
|-
| Dependence Liability
| align="center"| Extremely High
|-
| Routes
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV
|-
|}

==Uses==

Morphine is used legally:

*analgesic in hospital settings for
*Pain after surgery
*Pain associated with trauma
*In the relief of severe chronic pain
*Cancer pain
*Pain from kidney stones
*Back pain
*In epidural anesthesia
*As an antitussive for severe cough
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS)
*To relieve breathlessness in patients in respiratory failure

==Pharmacology of Morphine==

Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.

{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|align="left" colspan="3" bgcolor="white"|
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 11:48:06 GMT Standard Time 2006
ATOM 1 O1 MOL 1 18.255 13.156 0.573 1.00 0.00
ATOM 2 C2 MOL 1 17.569 14.167 -0.163 1.00 0.00
ATOM 3 C3 MOL 1 16.417 14.732 0.663 1.00 0.00
ATOM 4 C4 MOL 1 18.496 15.366 -0.471 1.00 0.00
ATOM 5 C5 MOL 1 17.015 13.567 -1.482 1.00 0.00
ATOM 6 C6 MOL 1 15.693 15.779 0.018 1.00 0.00
ATOM 7 C7 MOL 1 15.307 13.777 1.020 1.00 0.00
ATOM 8 C8 MOL 1 16.942 15.313 2.010 1.00 0.00
ATOM 9 C9 MOL 1 17.646 16.451 -1.361 1.00 0.00
ATOM 10 N10 MOL 1 19.019 15.899 0.861 1.00 0.00
ATOM 11 C11 MOL 1 15.959 12.473 -1.196 1.00 0.00
ATOM 12 C12 MOL 1 14.403 15.799 0.518 1.00 0.00
ATOM 13 C13 MOL 1 16.179 16.645 -0.862 1.00 0.00
ATOM 14 O14 MOL 1 14.159 14.689 1.403 1.00 0.00
ATOM 15 C15 MOL 1 14.899 12.986 -0.210 1.00 0.00
ATOM 16 C16 MOL 1 17.969 16.420 1.747 1.00 0.00
ATOM 17 C17 MOL 1 20.056 16.927 0.663 1.00 0.00
ATOM 18 C18 MOL 1 13.566 16.775 0.184 1.00 0.00
ATOM 19 C19 MOL 1 15.281 17.721 -1.321 1.00 0.00
ATOM 20 O20 MOL 1 13.720 12.646 -0.346 1.00 0.00
ATOM 21 C21 MOL 1 21.259 16.286 0.008 1.00 0.00
ATOM 22 O22 MOL 1 12.278 16.816 0.702 1.00 0.00
ATOM 23 C23 MOL 1 14.040 17.798 -0.803 1.00 0.00
ATOM 24 C24 MOL 1 22.410 16.944 -0.094 1.00 0.00
ATOM 25 H25 MOL 1 19.357 15.031 -1.060 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 11:49:10 GMT Standard Time 2006
ATOM 1 O1 MOL 1 17.558 13.998 -0.496 1.00 0.00
ATOM 2 C2 MOL 1 17.076 15.115 0.248 1.00 0.00
ATOM 3 C3 MOL 1 17.258 16.394 -0.557 1.00 0.00
ATOM 4 C4 MOL 1 15.561 15.011 0.531 1.00 0.00
ATOM 5 C5 MOL 1 17.860 15.228 1.589 1.00 0.00
ATOM 6 C6 MOL 1 16.778 17.574 0.073 1.00 0.00
ATOM 7 C7 MOL 1 18.653 16.799 -0.879 1.00 0.00
ATOM 8 C8 MOL 1 16.508 16.294 -1.921 1.00 0.00
ATOM 9 C9 MOL 1 15.127 16.315 1.434 1.00 0.00
ATOM 10 N10 MOL 1 14.843 14.899 -0.812 1.00 0.00
ATOM 11 C11 MOL 1 19.354 15.543 1.336 1.00 0.00
ATOM 12 C12 MOL 1 17.493 18.660 -0.426 1.00 0.00
ATOM 13 C13 MOL 1 15.791 17.648 0.954 1.00 0.00
ATOM 14 O14 MOL 1 18.548 18.231 -1.333 1.00 0.00
ATOM 15 C15 MOL 1 19.467 16.754 0.400 1.00 0.00
ATOM 16 C16 MOL 1 15.014 16.064 -1.686 1.00 0.00
ATOM 17 C17 MOL 1 13.406 14.609 -0.651 1.00 0.00
ATOM 18 C18 MOL 1 17.129 19.900 -0.114 1.00 0.00
ATOM 19 C19 MOL 1 15.387 18.995 1.400 1.00 0.00
ATOM 20 O20 MOL 1 20.317 17.624 0.613 1.00 0.00
ATOM 21 C21 MOL 1 13.178 13.073 -0.836 1.00 0.00
ATOM 22 O22 MOL 1 17.801 20.995 -0.638 1.00 0.00
ATOM 23 C23 MOL 1 16.014 20.069 0.881 1.00 0.00
ATOM 24 C24 MOL 1 11.870 12.702 -0.129 1.00 0.00
ATOM 25 C25 MOL 1 13.234 12.318 0.500 1.00 0.00
ATOM 26 H26 MOL 1 19.132 16.101 -1.579 1.00 0.00
ATOM 27 H27 MOL 1 15.339 14.101 1.101 1.00 0.00
TER</inlineContents>
</jmolApplet>
</jmol>
|-
|align="left" colspan="3" bgcolor="white"|Naloxone
|Naltrexone
|-
|}

Both naloxone and naltrexone are competitive antagonists at the μ- and κ-opioid receptors, and to a lesser extent at δ-opioid receptors. The blockade of these receptors is what prevents the opiods such as morphine, from combining with these receptor sites thus preventing the side effects usually caused by morphine.

==Derrivatives of Morphine==

Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:
<br>
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]
|[[Image:codeine.gif]]
|[[Image:heroin.gif]]
|-
|align="left" colspan="3" bgcolor="white"|Morphine
|Codeine
|Heroin
|-
|align="left" colspan="3" bgcolor="white"|
|
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>
REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 14:36:05 GMT Standard Time 2006
ATOM 1 O1 MOL 1 12.755 17.484 0.278 1.00 0.00
ATOM 2 C2 MOL 1 14.165 17.279 0.259 1.00 0.00
ATOM 3 C3 MOL 1 14.598 16.294 -0.907 1.00 0.00
ATOM 4 C4 MOL 1 14.783 17.091 1.590 1.00 0.00
ATOM 5 C5 MOL 1 16.085 15.955 -0.655 1.00 0.00
ATOM 6 O6 MOL 1 13.944 14.927 -0.976 1.00 0.00
ATOM 7 C7 MOL 1 16.137 17.074 1.556 1.00 0.00
ATOM 8 C8 MOL 1 15.986 14.685 0.099 1.00 0.00
ATOM 9 C9 MOL 1 16.902 16.950 0.154 1.00 0.00
ATOM 10 C10 MOL 1 16.709 15.628 -2.040 1.00 0.00
ATOM 11 C11 MOL 1 14.759 14.077 -0.164 1.00 0.00
ATOM 12 C12 MOL 1 16.917 14.157 0.888 1.00 0.00
ATOM 13 C13 MOL 1 18.319 16.318 0.340 1.00 0.00
ATOM 14 C14 MOL 1 18.152 15.134 -1.868 1.00 0.00
ATOM 15 C15 MOL 1 14.483 12.853 0.325 1.00 0.00
ATOM 16 C16 MOL 1 18.177 14.972 1.210 1.00 0.00
ATOM 17 C17 MOL 1 16.666 12.844 1.470 1.00 0.00
ATOM 18 N18 MOL 1 18.922 16.087 -1.029 1.00 0.00
ATOM 19 O19 MOL 1 13.263 12.126 0.120 1.00 0.00
ATOM 20 C20 MOL 1 15.521 12.211 1.182 1.00 0.00
ATOM 21 C21 MOL 1 20.289 15.567 -0.871 1.00 0.00
ATOM 22 C22 MOL 1 12.251 12.761 -0.671 1.00 0.00
ATOM 23 H23 MOL 1 16.955 17.909 -0.379 1.00 0.00
ATOM 24 H24 MOL 1 14.357 16.925 -1.773 1.00 0.00
ATOM 25 H25 MOL 1 18.981 17.000 0.892 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>
REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 14:36:49 GMT Standard Time 2006
ATOM 1 O1 MOL 1 21.380 10.913 -0.058 1.00 0.00
ATOM 2 C2 MOL 1 22.712 10.864 -0.568 1.00 0.00
ATOM 3 C3 MOL 1 20.932 12.266 -0.071 1.00 0.00
ATOM 4 C4 MOL 1 23.445 9.558 -0.647 1.00 0.00
ATOM 5 O5 MOL 1 23.307 11.901 -0.901 1.00 0.00
ATOM 6 C6 MOL 1 19.783 12.581 0.994 1.00 0.00
ATOM 7 C7 MOL 1 20.757 12.864 -1.427 1.00 0.00
ATOM 8 C8 MOL 1 19.419 14.067 0.744 1.00 0.00
ATOM 9 O9 MOL 1 18.395 11.892 1.004 1.00 0.00
ATOM 10 C10 MOL 1 20.623 14.207 -1.407 1.00 0.00
ATOM 11 C11 MOL 1 18.168 13.977 -0.025 1.00 0.00
ATOM 12 C12 MOL 1 20.420 14.937 -0.012 1.00 0.00
ATOM 13 C13 MOL 1 19.051 14.641 2.138 1.00 0.00
ATOM 14 C14 MOL 1 17.546 12.770 0.237 1.00 0.00
ATOM 15 C15 MOL 1 17.644 14.930 -0.793 1.00 0.00
ATOM 16 C16 MOL 1 19.772 16.333 -0.179 1.00 0.00
ATOM 17 C17 MOL 1 18.538 16.078 2.002 1.00 0.00
ATOM 18 C18 MOL 1 16.298 12.542 -0.183 1.00 0.00
ATOM 19 C19 MOL 1 18.462 16.189 -1.090 1.00 0.00
ATOM 20 C20 MOL 1 16.318 14.720 -1.345 1.00 0.00
ATOM 21 N21 MOL 1 19.493 16.889 1.202 1.00 0.00
ATOM 22 O22 MOL 1 15.642 11.319 0.166 1.00 0.00
ATOM 23 C23 MOL 1 15.656 13.605 -1.022 1.00 0.00
ATOM 24 C24 MOL 1 18.950 18.247 1.075 1.00 0.00
ATOM 25 C25 MOL 1 14.263 11.150 -0.231 1.00 0.00
ATOM 26 C26 MOL 1 13.567 9.867 0.115 1.00 0.00
ATOM 27 O27 MOL 1 13.607 12.019 -0.820 1.00 0.00
ATOM 28 H28 MOL 1 21.358 14.995 0.556 1.00 0.00
ATOM 29 H29 MOL 1 20.362 12.366 1.900 1.00 0.00
ATOM 30 H30 MOL 1 20.458 17.021 -0.692 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|-
|}
<br>
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br>
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br>
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.

<br>

==Synthesis of Codeine from Morphine==
[[Image:codeine_s.gif|thumb|Synthesis of Codeine]]

==Contraindications==

*Acute Respiratory Depression
*Acute Alcoholism
*Acute pancreatitis (this may be a result of morphine use as well)
*Renal failure (due to accumulation of the metabolite morphine-6-glucuronide)

==References and External Links==
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine
*Morphine, Molecule of the Month
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]
*Schmitz J, Stotts A, Rhoades H, Grabowski J. "Naltrexone and relapse prevention treatment for cocaine-dependent patients.". Addict Behav 26 (2): 167-80. PMID 11316375.
*Chicago Recovery Alliance's naloxone distrobution project
*Synthesis of codeine from morphine. Ai, Lin; Chen, Xiaoyuan; Zhang, Le. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005)

It:Retinal

2006-10-27T10:04:52Z

Sv205:

__toc__

'''Retinal''', also known as retinaldehyde or retinene<sub>1</sub> is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.

== Structure of Cis-Retinal ==

{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" bgcolor="lt blue"|'''2D Structure'''
| align="center" bgcolor="lt blue"|'''3D Structure'''
|-
| [[image:Cis-RetinalSo.gif]]
|<jmol>
<jmolApplet>
<size>350</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 54
CONECT 2 1 3 4 0 NONE 55
CONECT 4 2 5 6 0 NONE 56
CONECT 6 4 7 11 0 NONE 57
CONECT 7 6 8 9 10 NONE 58
CONECT 11 6 12 13 0 NONE 59
CONECT 13 11 14 15 0 NONE 60
CONECT 15 13 16 17 0 NONE 61
CONECT 17 15 18 22 0 NONE 62
CONECT 18 17 19 20 21 NONE 63
CONECT 22 17 23 24 0 NONE 64
CONECT 24 22 25 26 0 NONE 65
CONECT 26 24 41 27 0 NONE 66
CONECT 27 26 28 32 0 NONE 67
CONECT 28 27 29 30 31 NONE 68
CONECT 32 27 33 34 35 NONE 69
CONECT 35 32 36 37 38 NONE 70
CONECT 38 35 39 40 41 NONE 71
CONECT 41 38 26 42 46 NONE 72
CONECT 42 41 43 44 45 NONE 73
CONECT 46 41 47 48 49 NONE 74
END NONE 75
NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|}

== Properties of Cis-Retinal and Trans-Retinal ==

{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="1" bgcolor="lt blue"|
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Cis-Retinal'''
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Trans-Retinal'''
|-
| align="center" colspan="3" bgcolor="white"|'''General properties'''
|-
| Chemical name
| align="center"|(11Z)-retinal
| align="center"|...
|-
| Chemical formula
| align="center"|C<sub>20</sub>H<sub>28</sub>O
| align="center"|C<sub>20</sub>H<sub>28</sub>O
|-
| Molecular mass
| align="center"|284 g/mol
| align="center"|284 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|... °C
| align="center"|... °C
|-
| Boiling point
| align="center"|... °C
| align="center"|... °C
|-
| Appearance
| align="center"|...
| align="center"|...
|-
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous'''
|-
| SMILES
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)
=C(C)CCC1
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=O)
=C(C)CCC1
|-
|}

==Structure of all-trans retinal==
'''2D Structure'''

[[Image:AllTransRetinal.gif]]

==The role of retinal in the vision process==

The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.

[[Image:RetinalConversion.png]]
<br>Compound A 3D Picture

<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; cpk ;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY CRETAL01
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 13.180 7.499 17.803 90.00 95.66 90.00 P 21/n 4
ATOM 1 C1 UNK 0 1 3.279 5.402 15.975 1.00 0.00
ATOM 2 C2 UNK 0 1 4.046 6.337 15.055 1.00 0.00
ATOM 3 C3 UNK 0 1 3.501 7.731 15.036 1.00 0.00
ATOM 4 C4 UNK 0 1 2.048 7.716 14.547 1.00 0.00
ATOM 5 C5 UNK 0 1 1.242 6.570 15.071 1.00 0.00
ATOM 6 C6 UNK 0 1 1.742 5.525 15.720 1.00 0.00
ATOM 7 C7 UNK 0 1 0.960 4.412 16.249 1.00 0.00
ATOM 8 C8 UNK 0 1 -0.096 3.785 15.688 1.00 0.00
ATOM 9 C9 UNK 0 1 -0.891 2.748 16.260 1.00 0.00
ATOM 10 C10 UNK 0 1 -2.039 2.359 15.656 1.00 0.00
ATOM 11 C11 UNK 0 1 -2.995 1.432 16.171 1.00 0.00
ATOM 12 C12 UNK 0 1 -4.118 0.952 15.603 1.00 0.00
ATOM 13 C13 UNK 0 1 -4.579 1.155 14.210 1.00 0.00
ATOM 14 C14 UNK 0 1 -3.772 1.162 13.168 1.00 0.00
ATOM 15 C15 UNK 0 1 -4.144 1.290 11.748 1.00 0.00
ATOM 16 O1 UNK 0 1 -3.417 1.200 10.832 1.00 0.00
ATOM 17 C16 UNK 0 1 -0.251 6.757 14.825 1.00 0.00
ATOM 18 C17 UNK 0 1 3.537 5.722 17.465 1.00 0.00
ATOM 19 C18 UNK 0 1 3.755 3.989 15.704 1.00 0.00
ATOM 20 C19 UNK 0 1 -0.446 2.130 17.555 1.00 0.00
ATOM 21 C20 UNK 0 1 -6.097 1.275 14.125 1.00 0.00
ATOM 22 H1 UNK 0 1 4.961 6.299 15.236 1.00 0.00
ATOM 23 H2 UNK 0 1 4.033 6.074 13.960 1.00 0.00
ATOM 24 H3 UNK 0 1 3.361 8.099 16.086 1.00 0.00
ATOM 25 H4 UNK 0 1 4.112 8.346 14.368 1.00 0.00
ATOM 26 H5 UNK 0 1 1.613 8.609 14.846 1.00 0.00
ATOM 27 H6 UNK 0 1 2.096 8.271 13.429 1.00 0.00
ATOM 28 H7 UNK 0 1 1.167 4.027 17.220 1.00 0.00
ATOM 29 H8 UNK 0 1 -0.283 4.132 14.828 1.00 0.00
ATOM 30 H9 UNK 0 1 -2.166 2.700 14.811 1.00 0.00
ATOM 31 H10 UNK 0 1 -2.959 1.140 17.220 1.00 0.00
ATOM 32 H11 UNK 0 1 -4.766 0.337 16.175 1.00 0.00
ATOM 33 H12 UNK 0 1 -2.863 1.012 13.199 1.00 0.00
ATOM 34 H13 UNK 0 1 -5.051 1.500 11.604 1.00 0.00
ATOM 35 H14 UNK 0 1 -0.500 7.641 14.882 1.00 0.00
ATOM 36 H15 UNK 0 1 -0.354 6.404 13.677 1.00 0.00
ATOM 37 H16 UNK 0 1 -0.828 6.374 15.537 1.00 0.00
ATOM 38 H17 UNK 0 1 4.443 5.482 17.539 1.00 0.00
ATOM 39 H18 UNK 0 1 3.171 6.749 17.876 1.00 0.00
ATOM 40 H19 UNK 0 1 2.971 5.092 18.159 1.00 0.00
ATOM 41 H20 UNK 0 1 3.359 3.330 16.246 1.00 0.00
ATOM 42 H21 UNK 0 1 3.564 3.712 14.704 1.00 0.00
ATOM 43 H22 UNK 0 1 4.832 3.967 15.608 1.00 0.00
ATOM 44 H23 UNK 0 1 0.526 2.025 17.433 1.00 0.00
ATOM 45 H24 UNK 0 1 -0.489 2.700 18.230 1.00 0.00
ATOM 46 H25 UNK 0 1 -1.006 1.387 18.000 1.00 0.00
ATOM 47 H26 UNK 0 1 -6.646 0.300 14.793 1.00 0.00
ATOM 48 H27 UNK 0 1 -6.440 2.100 14.580 1.00 0.00
ATOM 49 H28 UNK 0 1 -6.271 1.320 13.269 1.00 0.00
CONECT 1 2 6 18 19
CONECT 2 1 3 22 23
CONECT 3 2 4 24 25
CONECT 4 3 5 26 27
CONECT 5 4 6 17
CONECT 6 1 5 7
CONECT 7 6 8 28
CONECT 8 7 9 29
CONECT 9 8 10 20
CONECT 10 9 11 30
CONECT 11 10 12 31
CONECT 12 11 13 32
CONECT 13 12 14 21
CONECT 14 13 15 33
CONECT 15 14 16 34
CONECT 16 15
CONECT 17 5 35 36 37
CONECT 18 1 38 39 40
CONECT 19 1 41 42 43
CONECT 20 9 44 45 46
CONECT 21 13 47 48 49
CONECT 22 2
CONECT 23 2
CONECT 24 3
CONECT 25 3
CONECT 26 4
CONECT 27 4
CONECT 28 7
CONECT 29 8
CONECT 30 10
CONECT 31 11
CONECT 32 12
CONECT 33 14
CONECT 34 15
CONECT 35 17
CONECT 36 17
CONECT 37 17
CONECT 38 18
CONECT 39 18
CONECT 40 18
CONECT 41 19
CONECT 42 19
CONECT 43 19
CONECT 44 20
CONECT 45 20
CONECT 46 20
CONECT 47 21
CONECT 48 21
CONECT 49 21
MASTER 0 0 0 0 0 0 0 0 49 0 49 0
END</inlineContents>
</jmolApplet>
</jmol>

Compound B 3D picture

<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; cpk ;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY TRETAL03
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 14.956 8.277 15.291 90.00 104.92 90.00 P 21/n 4
ATOM 1 O1 UNK 0 1 9.309 3.852 9.139 1.00 0.00
ATOM 2 C1 UNK 0 1 -1.723 -0.739 4.047 1.00 0.00
ATOM 3 C2 UNK 0 1 -0.452 -1.316 3.444 1.00 0.00
ATOM 4 C3 UNK 0 1 -2.519 -1.832 4.761 1.00 0.00
ATOM 5 C4 UNK 0 1 -2.460 -0.197 2.791 1.00 0.00
ATOM 6 C5 UNK 0 1 -3.484 0.764 3.073 1.00 0.00
ATOM 7 C6 UNK 0 1 -3.039 1.904 3.908 1.00 0.00
ATOM 8 C7 UNK 0 1 -2.002 1.579 4.954 1.00 0.00
ATOM 9 C8 UNK 0 1 -1.767 2.692 5.929 1.00 0.00
ATOM 10 C9 UNK 0 1 -1.402 0.397 5.000 1.00 0.00
ATOM 11 C10 UNK 0 1 -0.360 0.092 6.017 1.00 0.00
ATOM 12 C11 UNK 0 1 0.764 0.756 6.175 1.00 0.00
ATOM 13 C12 UNK 0 1 1.826 0.493 7.151 1.00 0.00
ATOM 14 C13 UNK 0 1 1.604 -0.603 8.138 1.00 0.00
ATOM 15 C14 UNK 0 1 2.930 1.234 7.109 1.00 0.00
ATOM 16 C15 UNK 0 1 4.081 1.142 7.980 1.00 0.00
ATOM 17 C16 UNK 0 1 5.145 1.932 7.893 1.00 0.00
ATOM 18 C17 UNK 0 1 6.289 1.962 8.796 1.00 0.00
ATOM 19 C18 UNK 0 1 6.288 1.002 9.940 1.00 0.00
ATOM 20 C19 UNK 0 1 7.263 2.851 8.564 1.00 0.00
ATOM 21 C20 UNK 0 1 8.452 3.036 9.396 1.00 0.00
CONECT 1 21
CONECT 2 3 4 5 10
CONECT 3 2
CONECT 4 2
CONECT 5 2 6
CONECT 6 5 7
CONECT 7 6 8
CONECT 8 7 9 10
CONECT 9 8
CONECT 10 2 8 11
CONECT 11 10 12
CONECT 12 11 13
CONECT 13 12 14 15
CONECT 14 13
CONECT 15 13 16
CONECT 16 15 17
CONECT 17 16 18
CONECT 18 17 19 20
CONECT 19 18
CONECT 20 18 21
CONECT 21 1 20
MASTER 0 0 0 0 0 0 0 0 21 0 21 0
END</inlineContents>
</jmolApplet>
</jmol>

==Synthesis of Rhodopsin==
[[Image:Synthesis_of_rhodopsin.gif]]

==Effects of Bunazosin on ocular circulation and retinal neuronal damage==

By applying bunazosin hydrochloride into a healthy humans, it increases the blood velocity in the optic nerve head(ONH),retina and choroid, without changing either heart rate and blood pressure dramaticallt. This drup also applied to rabit and rat which gave positive results. These shows that bunazosin hydrochloride have improvement effect both in the ocular circulation and a direct neuroprotective effct. Therefore, it may be useful to use bunazosin hydrochloride as a therapeutic drug against retinal diseases which is associated with the ocular circulation.

== References ==

*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH

*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0.
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.
*3.Hara, Hideaki / Ichikawa, Masaki / Oku, Hidehiro / Shimazawa, Masamitsu / Araie, Makoto, Cardiovascular drug reviews, Apr 2005

It:Retinal

2006-10-27T10:03:21Z

Sv205: 3d pictures edit

__toc__

'''Retinal''', also known as retinaldehyde or retinene<sub>1</sub> is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.

== Structure of Cis-Retinal ==

{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" bgcolor="lt blue"|'''2D Structure'''
| align="center" bgcolor="lt blue"|'''3D Structure'''
|-
| [[image:Cis-RetinalSo.gif]]
|<jmol>
<jmolApplet>
<size>350</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 54
CONECT 2 1 3 4 0 NONE 55
CONECT 4 2 5 6 0 NONE 56
CONECT 6 4 7 11 0 NONE 57
CONECT 7 6 8 9 10 NONE 58
CONECT 11 6 12 13 0 NONE 59
CONECT 13 11 14 15 0 NONE 60
CONECT 15 13 16 17 0 NONE 61
CONECT 17 15 18 22 0 NONE 62
CONECT 18 17 19 20 21 NONE 63
CONECT 22 17 23 24 0 NONE 64
CONECT 24 22 25 26 0 NONE 65
CONECT 26 24 41 27 0 NONE 66
CONECT 27 26 28 32 0 NONE 67
CONECT 28 27 29 30 31 NONE 68
CONECT 32 27 33 34 35 NONE 69
CONECT 35 32 36 37 38 NONE 70
CONECT 38 35 39 40 41 NONE 71
CONECT 41 38 26 42 46 NONE 72
CONECT 42 41 43 44 45 NONE 73
CONECT 46 41 47 48 49 NONE 74
END NONE 75
NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|}

== Properties of Cis-Retinal and Trans-Retinal ==

{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="1" bgcolor="lt blue"|
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Cis-Retinal'''
| align="center" colspan="1" bgcolor="lt blue"|'''Properties of Trans-Retinal'''
|-
| align="center" colspan="3" bgcolor="white"|'''General properties'''
|-
| Chemical name
| align="center"|(11Z)-retinal
| align="center"|...
|-
| Chemical formula
| align="center"|C<sub>20</sub>H<sub>28</sub>O
| align="center"|C<sub>20</sub>H<sub>28</sub>O
|-
| Molecular mass
| align="center"|284 g/mol
| align="center"|284 g/mol
|-
| align="center" colspan="3" bgcolor="white"|'''Physical properties'''
|-
| Melting point
| align="center"|... °C
| align="center"|... °C
|-
| Boiling point
| align="center"|... °C
| align="center"|... °C
|-
| Appearance
| align="center"|...
| align="center"|...
|-
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous'''
|-
| SMILES
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)
=C(C)CCC1
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=O)
=C(C)CCC1
|-
|}

==Structure of all-trans retinal==
'''2D Structure'''

[[Image:AllTransRetinal.gif]]

==The role of retinal in the vision process==

The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.

[[Image:RetinalConversion.png]]
<br>Compound A 3D Picture

<jmol>
<jmolApplet>
<size>300</size>
<color>Black</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY CRETAL01
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 13.180 7.499 17.803 90.00 95.66 90.00 P 21/n 4
ATOM 1 C1 UNK 0 1 3.279 5.402 15.975 1.00 0.00
ATOM 2 C2 UNK 0 1 4.046 6.337 15.055 1.00 0.00
ATOM 3 C3 UNK 0 1 3.501 7.731 15.036 1.00 0.00
ATOM 4 C4 UNK 0 1 2.048 7.716 14.547 1.00 0.00
ATOM 5 C5 UNK 0 1 1.242 6.570 15.071 1.00 0.00
ATOM 6 C6 UNK 0 1 1.742 5.525 15.720 1.00 0.00
ATOM 7 C7 UNK 0 1 0.960 4.412 16.249 1.00 0.00
ATOM 8 C8 UNK 0 1 -0.096 3.785 15.688 1.00 0.00
ATOM 9 C9 UNK 0 1 -0.891 2.748 16.260 1.00 0.00
ATOM 10 C10 UNK 0 1 -2.039 2.359 15.656 1.00 0.00
ATOM 11 C11 UNK 0 1 -2.995 1.432 16.171 1.00 0.00
ATOM 12 C12 UNK 0 1 -4.118 0.952 15.603 1.00 0.00
ATOM 13 C13 UNK 0 1 -4.579 1.155 14.210 1.00 0.00
ATOM 14 C14 UNK 0 1 -3.772 1.162 13.168 1.00 0.00
ATOM 15 C15 UNK 0 1 -4.144 1.290 11.748 1.00 0.00
ATOM 16 O1 UNK 0 1 -3.417 1.200 10.832 1.00 0.00
ATOM 17 C16 UNK 0 1 -0.251 6.757 14.825 1.00 0.00
ATOM 18 C17 UNK 0 1 3.537 5.722 17.465 1.00 0.00
ATOM 19 C18 UNK 0 1 3.755 3.989 15.704 1.00 0.00
ATOM 20 C19 UNK 0 1 -0.446 2.130 17.555 1.00 0.00
ATOM 21 C20 UNK 0 1 -6.097 1.275 14.125 1.00 0.00
ATOM 22 H1 UNK 0 1 4.961 6.299 15.236 1.00 0.00
ATOM 23 H2 UNK 0 1 4.033 6.074 13.960 1.00 0.00
ATOM 24 H3 UNK 0 1 3.361 8.099 16.086 1.00 0.00
ATOM 25 H4 UNK 0 1 4.112 8.346 14.368 1.00 0.00
ATOM 26 H5 UNK 0 1 1.613 8.609 14.846 1.00 0.00
ATOM 27 H6 UNK 0 1 2.096 8.271 13.429 1.00 0.00
ATOM 28 H7 UNK 0 1 1.167 4.027 17.220 1.00 0.00
ATOM 29 H8 UNK 0 1 -0.283 4.132 14.828 1.00 0.00
ATOM 30 H9 UNK 0 1 -2.166 2.700 14.811 1.00 0.00
ATOM 31 H10 UNK 0 1 -2.959 1.140 17.220 1.00 0.00
ATOM 32 H11 UNK 0 1 -4.766 0.337 16.175 1.00 0.00
ATOM 33 H12 UNK 0 1 -2.863 1.012 13.199 1.00 0.00
ATOM 34 H13 UNK 0 1 -5.051 1.500 11.604 1.00 0.00
ATOM 35 H14 UNK 0 1 -0.500 7.641 14.882 1.00 0.00
ATOM 36 H15 UNK 0 1 -0.354 6.404 13.677 1.00 0.00
ATOM 37 H16 UNK 0 1 -0.828 6.374 15.537 1.00 0.00
ATOM 38 H17 UNK 0 1 4.443 5.482 17.539 1.00 0.00
ATOM 39 H18 UNK 0 1 3.171 6.749 17.876 1.00 0.00
ATOM 40 H19 UNK 0 1 2.971 5.092 18.159 1.00 0.00
ATOM 41 H20 UNK 0 1 3.359 3.330 16.246 1.00 0.00
ATOM 42 H21 UNK 0 1 3.564 3.712 14.704 1.00 0.00
ATOM 43 H22 UNK 0 1 4.832 3.967 15.608 1.00 0.00
ATOM 44 H23 UNK 0 1 0.526 2.025 17.433 1.00 0.00
ATOM 45 H24 UNK 0 1 -0.489 2.700 18.230 1.00 0.00
ATOM 46 H25 UNK 0 1 -1.006 1.387 18.000 1.00 0.00
ATOM 47 H26 UNK 0 1 -6.646 0.300 14.793 1.00 0.00
ATOM 48 H27 UNK 0 1 -6.440 2.100 14.580 1.00 0.00
ATOM 49 H28 UNK 0 1 -6.271 1.320 13.269 1.00 0.00
CONECT 1 2 6 18 19
CONECT 2 1 3 22 23
CONECT 3 2 4 24 25
CONECT 4 3 5 26 27
CONECT 5 4 6 17
CONECT 6 1 5 7
CONECT 7 6 8 28
CONECT 8 7 9 29
CONECT 9 8 10 20
CONECT 10 9 11 30
CONECT 11 10 12 31
CONECT 12 11 13 32
CONECT 13 12 14 21
CONECT 14 13 15 33
CONECT 15 14 16 34
CONECT 16 15
CONECT 17 5 35 36 37
CONECT 18 1 38 39 40
CONECT 19 1 41 42 43
CONECT 20 9 44 45 46
CONECT 21 13 47 48 49
CONECT 22 2
CONECT 23 2
CONECT 24 3
CONECT 25 3
CONECT 26 4
CONECT 27 4
CONECT 28 7
CONECT 29 8
CONECT 30 10
CONECT 31 11
CONECT 32 12
CONECT 33 14
CONECT 34 15
CONECT 35 17
CONECT 36 17
CONECT 37 17
CONECT 38 18
CONECT 39 18
CONECT 40 18
CONECT 41 19
CONECT 42 19
CONECT 43 19
CONECT 44 20
CONECT 45 20
CONECT 46 20
CONECT 47 21
CONECT 48 21
CONECT 49 21
MASTER 0 0 0 0 0 0 0 0 49 0 49 0
END</inlineContents>
</jmolApplet>
</jmol>

Compound B 3D picture

<jmol>
<jmolApplet>
<size>300</size>
<color>black</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY TRETAL03
COMPND UNNAMED
AUTHOR GENERATED BY CONQUEST
CRYST1 14.956 8.277 15.291 90.00 104.92 90.00 P 21/n 4
ATOM 1 O1 UNK 0 1 9.309 3.852 9.139 1.00 0.00
ATOM 2 C1 UNK 0 1 -1.723 -0.739 4.047 1.00 0.00
ATOM 3 C2 UNK 0 1 -0.452 -1.316 3.444 1.00 0.00
ATOM 4 C3 UNK 0 1 -2.519 -1.832 4.761 1.00 0.00
ATOM 5 C4 UNK 0 1 -2.460 -0.197 2.791 1.00 0.00
ATOM 6 C5 UNK 0 1 -3.484 0.764 3.073 1.00 0.00
ATOM 7 C6 UNK 0 1 -3.039 1.904 3.908 1.00 0.00
ATOM 8 C7 UNK 0 1 -2.002 1.579 4.954 1.00 0.00
ATOM 9 C8 UNK 0 1 -1.767 2.692 5.929 1.00 0.00
ATOM 10 C9 UNK 0 1 -1.402 0.397 5.000 1.00 0.00
ATOM 11 C10 UNK 0 1 -0.360 0.092 6.017 1.00 0.00
ATOM 12 C11 UNK 0 1 0.764 0.756 6.175 1.00 0.00
ATOM 13 C12 UNK 0 1 1.826 0.493 7.151 1.00 0.00
ATOM 14 C13 UNK 0 1 1.604 -0.603 8.138 1.00 0.00
ATOM 15 C14 UNK 0 1 2.930 1.234 7.109 1.00 0.00
ATOM 16 C15 UNK 0 1 4.081 1.142 7.980 1.00 0.00
ATOM 17 C16 UNK 0 1 5.145 1.932 7.893 1.00 0.00
ATOM 18 C17 UNK 0 1 6.289 1.962 8.796 1.00 0.00
ATOM 19 C18 UNK 0 1 6.288 1.002 9.940 1.00 0.00
ATOM 20 C19 UNK 0 1 7.263 2.851 8.564 1.00 0.00
ATOM 21 C20 UNK 0 1 8.452 3.036 9.396 1.00 0.00
CONECT 1 21
CONECT 2 3 4 5 10
CONECT 3 2
CONECT 4 2
CONECT 5 2 6
CONECT 6 5 7
CONECT 7 6 8
CONECT 8 7 9 10
CONECT 9 8
CONECT 10 2 8 11
CONECT 11 10 12
CONECT 12 11 13
CONECT 13 12 14 15
CONECT 14 13
CONECT 15 13 16
CONECT 16 15 17
CONECT 17 16 18
CONECT 18 17 19 20
CONECT 19 18
CONECT 20 18 21
CONECT 21 1 20
MASTER 0 0 0 0 0 0 0 0 21 0 21 0
END</inlineContents>
</jmolApplet>
</jmol>

==Synthesis of Rhodopsin==
[[Image:Synthesis_of_rhodopsin.gif]]

==Effects of Bunazosin on ocular circulation and retinal neuronal damage==

By applying bunazosin hydrochloride into a healthy humans, it increases the blood velocity in the optic nerve head(ONH),retina and choroid, without changing either heart rate and blood pressure dramaticallt. This drup also applied to rabit and rat which gave positive results. These shows that bunazosin hydrochloride have improvement effect both in the ocular circulation and a direct neuroprotective effct. Therefore, it may be useful to use bunazosin hydrochloride as a therapeutic drug against retinal diseases which is associated with the ocular circulation.

== References ==

*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH

*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0.
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.
*3.Hara, Hideaki / Ichikawa, Masaki / Oku, Hidehiro / Shimazawa, Masamitsu / Araie, Makoto, Cardiovascular drug reviews, Apr 2005

It:Morphine

2006-10-26T11:45:35Z

Sv205: synthesis of codeine

==Introduction to Morphine==

{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.

|colspan="5"|[[Image:poppy2.GIF]]
|-
|}

==Structure of Morphine==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|[[Image:200px-Morphine-2D-skeletal.GIF]]
|-
|}

== Properties of Morphine ==

{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data'''
|-
| IUPAC Name
| align="center"|7,8-didehydro-
4,5-epoxy-17-methylmorphinan-3,6-diol
|-
| Chemical formula
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub>
|-
| Molar Mass
| align="center"|285.4 g/mol
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''
|-
| Bioavailability
| align="center"|... ~30%
|-
| Protein binding
| align="center"|... 30–40%
|-
| Metabolism
| align="center"|... Hepatic 90%
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''
|-
| Pregnancy cat.
| align="center"| C(AU) C(US)
|-
| Legal status
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only
|-
| Dependence Liability
| align="center"| Extremely High
|-
| Routes
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV
|-
|}

==Uses==

Morphine is used legally:

*analgesic in hospital settings for
*Pain after surgery
*Pain associated with trauma
*In the relief of severe chronic pain
*Cancer pain
*Pain from kidney stones
*Back pain
*In epidural anesthesia
*As an antitussive for severe cough
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS)
*To relieve breathlessness in patients in respiratory failure

==Pharmacology of Morphine==

Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.

Naloxone
<jmol>
<jmolApplet>
<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 11:48:06 GMT Standard Time 2006
ATOM 1 O1 MOL 1 18.255 13.156 0.573 1.00 0.00
ATOM 2 C2 MOL 1 17.569 14.167 -0.163 1.00 0.00
ATOM 3 C3 MOL 1 16.417 14.732 0.663 1.00 0.00
ATOM 4 C4 MOL 1 18.496 15.366 -0.471 1.00 0.00
ATOM 5 C5 MOL 1 17.015 13.567 -1.482 1.00 0.00
ATOM 6 C6 MOL 1 15.693 15.779 0.018 1.00 0.00
ATOM 7 C7 MOL 1 15.307 13.777 1.020 1.00 0.00
ATOM 8 C8 MOL 1 16.942 15.313 2.010 1.00 0.00
ATOM 9 C9 MOL 1 17.646 16.451 -1.361 1.00 0.00
ATOM 10 N10 MOL 1 19.019 15.899 0.861 1.00 0.00
ATOM 11 C11 MOL 1 15.959 12.473 -1.196 1.00 0.00
ATOM 12 C12 MOL 1 14.403 15.799 0.518 1.00 0.00
ATOM 13 C13 MOL 1 16.179 16.645 -0.862 1.00 0.00
ATOM 14 O14 MOL 1 14.159 14.689 1.403 1.00 0.00
ATOM 15 C15 MOL 1 14.899 12.986 -0.210 1.00 0.00
ATOM 16 C16 MOL 1 17.969 16.420 1.747 1.00 0.00
ATOM 17 C17 MOL 1 20.056 16.927 0.663 1.00 0.00
ATOM 18 C18 MOL 1 13.566 16.775 0.184 1.00 0.00
ATOM 19 C19 MOL 1 15.281 17.721 -1.321 1.00 0.00
ATOM 20 O20 MOL 1 13.720 12.646 -0.346 1.00 0.00
ATOM 21 C21 MOL 1 21.259 16.286 0.008 1.00 0.00
ATOM 22 O22 MOL 1 12.278 16.816 0.702 1.00 0.00
ATOM 23 C23 MOL 1 14.040 17.798 -0.803 1.00 0.00
ATOM 24 C24 MOL 1 22.410 16.944 -0.094 1.00 0.00
ATOM 25 H25 MOL 1 19.357 15.031 -1.060 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>

Naltrexone
<jmol>
<jmolApplet>
<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 11:49:10 GMT Standard Time 2006
ATOM 1 O1 MOL 1 17.558 13.998 -0.496 1.00 0.00
ATOM 2 C2 MOL 1 17.076 15.115 0.248 1.00 0.00
ATOM 3 C3 MOL 1 17.258 16.394 -0.557 1.00 0.00
ATOM 4 C4 MOL 1 15.561 15.011 0.531 1.00 0.00
ATOM 5 C5 MOL 1 17.860 15.228 1.589 1.00 0.00
ATOM 6 C6 MOL 1 16.778 17.574 0.073 1.00 0.00
ATOM 7 C7 MOL 1 18.653 16.799 -0.879 1.00 0.00
ATOM 8 C8 MOL 1 16.508 16.294 -1.921 1.00 0.00
ATOM 9 C9 MOL 1 15.127 16.315 1.434 1.00 0.00
ATOM 10 N10 MOL 1 14.843 14.899 -0.812 1.00 0.00
ATOM 11 C11 MOL 1 19.354 15.543 1.336 1.00 0.00
ATOM 12 C12 MOL 1 17.493 18.660 -0.426 1.00 0.00
ATOM 13 C13 MOL 1 15.791 17.648 0.954 1.00 0.00
ATOM 14 O14 MOL 1 18.548 18.231 -1.333 1.00 0.00
ATOM 15 C15 MOL 1 19.467 16.754 0.400 1.00 0.00
ATOM 16 C16 MOL 1 15.014 16.064 -1.686 1.00 0.00
ATOM 17 C17 MOL 1 13.406 14.609 -0.651 1.00 0.00
ATOM 18 C18 MOL 1 17.129 19.900 -0.114 1.00 0.00
ATOM 19 C19 MOL 1 15.387 18.995 1.400 1.00 0.00
ATOM 20 O20 MOL 1 20.317 17.624 0.613 1.00 0.00
ATOM 21 C21 MOL 1 13.178 13.073 -0.836 1.00 0.00
ATOM 22 O22 MOL 1 17.801 20.995 -0.638 1.00 0.00
ATOM 23 C23 MOL 1 16.014 20.069 0.881 1.00 0.00
ATOM 24 C24 MOL 1 11.870 12.702 -0.129 1.00 0.00
ATOM 25 C25 MOL 1 13.234 12.318 0.500 1.00 0.00
ATOM 26 H26 MOL 1 19.132 16.101 -1.579 1.00 0.00
ATOM 27 H27 MOL 1 15.339 14.101 1.101 1.00 0.00
TER</inlineContents>
</jmolApplet>
</jmol>

Both naloxone and naltrexone are competitive antagonists at the μ- and κ-opioid receptors, and to a lesser extent at δ-opioid receptors. The blockade of these receptors is what prevents the opiods such as morphine, from combining with these receptor sites thus preventing the side effects usually caused by morphine.

==Derrivatives of Morphine==

Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:
<br>
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]
|[[Image:codeine.gif]]
|[[Image:heroin.gif]]
|-
|align="left" colspan="3" bgcolor="white"|Morphine
|Codeine
|Heroine
|-
|}
<br>
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br>
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br>
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.

<br>

==Synthesis of Codeine from Morphine==
[[Image:codeine_s.gif|thumb|Synthesis of Codeine]]

==References and External Links==
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine
*Morphine, Molecule of the Month
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]
*Schmitz J, Stotts A, Rhoades H, Grabowski J. "Naltrexone and relapse prevention treatment for cocaine-dependent patients.". Addict Behav 26 (2): 167-80. PMID 11316375.
*Chicago Recovery Alliance's naloxone distrobution project

It:Morphine

2006-10-26T11:42:15Z

Sv205: table of properties

==Introduction to Morphine==

{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.

|colspan="5"|[[Image:poppy2.GIF]]
|-
|}

==Structure of Morphine==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|[[Image:200px-Morphine-2D-skeletal.GIF]]
|-
|}

== Properties of Morphine ==

{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data'''
|-
| IUPAC Name
| align="center"|7,8-didehydro-
4,5-epoxy-17-methylmorphinan-3,6-diol
|-
| Chemical formula
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub>
|-
| Molar Mass
| align="center"|285.4 g/mol
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''
|-
| Bioavailability
| align="center"|... ~30%
|-
| Protein binding
| align="center"|... 30–40%
|-
| Metabolism
| align="center"|... Hepatic 90%
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''
|-
| Pregnancy cat.
| align="center"| C(AU) C(US)
|-
| Legal status
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only
|-
| Dependence Liability
| align="center"| Extremely High
|-
| Routes
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV
|-
|}

==Uses==

Morphine is used legally:

*analgesic in hospital settings for
*Pain after surgery
*Pain associated with trauma
*In the relief of severe chronic pain
*Cancer pain
*Pain from kidney stones
*Back pain
*In epidural anesthesia
*As an antitussive for severe cough
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS)
*To relieve breathlessness in patients in respiratory failure

==Pharmacology of Morphine==

Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.

Naloxone
<jmol>
<jmolApplet>
<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 11:48:06 GMT Standard Time 2006
ATOM 1 O1 MOL 1 18.255 13.156 0.573 1.00 0.00
ATOM 2 C2 MOL 1 17.569 14.167 -0.163 1.00 0.00
ATOM 3 C3 MOL 1 16.417 14.732 0.663 1.00 0.00
ATOM 4 C4 MOL 1 18.496 15.366 -0.471 1.00 0.00
ATOM 5 C5 MOL 1 17.015 13.567 -1.482 1.00 0.00
ATOM 6 C6 MOL 1 15.693 15.779 0.018 1.00 0.00
ATOM 7 C7 MOL 1 15.307 13.777 1.020 1.00 0.00
ATOM 8 C8 MOL 1 16.942 15.313 2.010 1.00 0.00
ATOM 9 C9 MOL 1 17.646 16.451 -1.361 1.00 0.00
ATOM 10 N10 MOL 1 19.019 15.899 0.861 1.00 0.00
ATOM 11 C11 MOL 1 15.959 12.473 -1.196 1.00 0.00
ATOM 12 C12 MOL 1 14.403 15.799 0.518 1.00 0.00
ATOM 13 C13 MOL 1 16.179 16.645 -0.862 1.00 0.00
ATOM 14 O14 MOL 1 14.159 14.689 1.403 1.00 0.00
ATOM 15 C15 MOL 1 14.899 12.986 -0.210 1.00 0.00
ATOM 16 C16 MOL 1 17.969 16.420 1.747 1.00 0.00
ATOM 17 C17 MOL 1 20.056 16.927 0.663 1.00 0.00
ATOM 18 C18 MOL 1 13.566 16.775 0.184 1.00 0.00
ATOM 19 C19 MOL 1 15.281 17.721 -1.321 1.00 0.00
ATOM 20 O20 MOL 1 13.720 12.646 -0.346 1.00 0.00
ATOM 21 C21 MOL 1 21.259 16.286 0.008 1.00 0.00
ATOM 22 O22 MOL 1 12.278 16.816 0.702 1.00 0.00
ATOM 23 C23 MOL 1 14.040 17.798 -0.803 1.00 0.00
ATOM 24 C24 MOL 1 22.410 16.944 -0.094 1.00 0.00
ATOM 25 H25 MOL 1 19.357 15.031 -1.060 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>

Naltrexone
<jmol>
<jmolApplet>
<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 11:49:10 GMT Standard Time 2006
ATOM 1 O1 MOL 1 17.558 13.998 -0.496 1.00 0.00
ATOM 2 C2 MOL 1 17.076 15.115 0.248 1.00 0.00
ATOM 3 C3 MOL 1 17.258 16.394 -0.557 1.00 0.00
ATOM 4 C4 MOL 1 15.561 15.011 0.531 1.00 0.00
ATOM 5 C5 MOL 1 17.860 15.228 1.589 1.00 0.00
ATOM 6 C6 MOL 1 16.778 17.574 0.073 1.00 0.00
ATOM 7 C7 MOL 1 18.653 16.799 -0.879 1.00 0.00
ATOM 8 C8 MOL 1 16.508 16.294 -1.921 1.00 0.00
ATOM 9 C9 MOL 1 15.127 16.315 1.434 1.00 0.00
ATOM 10 N10 MOL 1 14.843 14.899 -0.812 1.00 0.00
ATOM 11 C11 MOL 1 19.354 15.543 1.336 1.00 0.00
ATOM 12 C12 MOL 1 17.493 18.660 -0.426 1.00 0.00
ATOM 13 C13 MOL 1 15.791 17.648 0.954 1.00 0.00
ATOM 14 O14 MOL 1 18.548 18.231 -1.333 1.00 0.00
ATOM 15 C15 MOL 1 19.467 16.754 0.400 1.00 0.00
ATOM 16 C16 MOL 1 15.014 16.064 -1.686 1.00 0.00
ATOM 17 C17 MOL 1 13.406 14.609 -0.651 1.00 0.00
ATOM 18 C18 MOL 1 17.129 19.900 -0.114 1.00 0.00
ATOM 19 C19 MOL 1 15.387 18.995 1.400 1.00 0.00
ATOM 20 O20 MOL 1 20.317 17.624 0.613 1.00 0.00
ATOM 21 C21 MOL 1 13.178 13.073 -0.836 1.00 0.00
ATOM 22 O22 MOL 1 17.801 20.995 -0.638 1.00 0.00
ATOM 23 C23 MOL 1 16.014 20.069 0.881 1.00 0.00
ATOM 24 C24 MOL 1 11.870 12.702 -0.129 1.00 0.00
ATOM 25 C25 MOL 1 13.234 12.318 0.500 1.00 0.00
ATOM 26 H26 MOL 1 19.132 16.101 -1.579 1.00 0.00
ATOM 27 H27 MOL 1 15.339 14.101 1.101 1.00 0.00
TER</inlineContents>
</jmolApplet>
</jmol>

Both naloxone and naltrexone are competitive antagonists at the μ- and κ-opioid receptors, and to a lesser extent at δ-opioid receptors. The blockade of these receptors is what prevents the opiods such as morphine, from combining with these receptor sites thus preventing the side effects usually caused by morphine.

==Derrivatives of Morphine==

Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:
<br>
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]
|[[Image:codeine.gif]]
|[[Image:heroin.gif]]
|-
|align="left" colspan="3" bgcolor="white"|Morphine
|Codeine
|Heroine
|-
|}
<br>
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br>
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br>
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.

<br>
Click on the thumbnail to view the enlarged synthesis of codeine from morphine.
[[Image:codeine_s.gif|thumb|Synthesis of Codeine]]

==References and External Links==
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine
*Morphine, Molecule of the Month
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]
*Schmitz J, Stotts A, Rhoades H, Grabowski J. "Naltrexone and relapse prevention treatment for cocaine-dependent patients.". Addict Behav 26 (2): 167-80. PMID 11316375.
*Chicago Recovery Alliance's naloxone distrobution project

It:Morphine

2006-10-26T11:38:08Z

Sv205: /* References and External Links */

==Introduction to Morphine==

{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.

|colspan="5"|[[Image:poppy2.GIF]]
|-
|}

==Structure of Morphine==
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|<jmol>
<jmolApplet>
<size>300</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>
|[[Image:200px-Morphine-2D-skeletal.GIF]]
|-
|}

== Properties of Morphine ==

{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data'''
|-
| Chemical name
| align="center"|7,8-didehydro-
4,5-epoxy-17-methylmorphinan-3,6-diol
|-
| Chemical formula
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub>
|-
| Molar Mass
| align="center"|285.4 g/mol
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''
|-
| Bioavailability
| align="center"|... ~30%
|-
| Protein binding
| align="center"|... 30–40%
|-
| Metabolism
| align="center"|... Hepatic 90%
|-
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''
|-
| Pregnancy cat.
| align="center"| C(AU) C(US)
|-
| Legal status
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only
|-
| Dependence Liability
| align="center"| Extremely High
|-
| Routes
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV
|-
|}

==Uses==

Morphine is used legally:

*analgesic in hospital settings for
*Pain after surgery
*Pain associated with trauma
*In the relief of severe chronic pain
*Cancer pain
*Pain from kidney stones
*Back pain
*In epidural anesthesia
*As an antitussive for severe cough
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS)
*To relieve breathlessness in patients in respiratory failure

==Pharmacology of Morphine==

Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.

Naloxone
<jmol>
<jmolApplet>
<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 11:48:06 GMT Standard Time 2006
ATOM 1 O1 MOL 1 18.255 13.156 0.573 1.00 0.00
ATOM 2 C2 MOL 1 17.569 14.167 -0.163 1.00 0.00
ATOM 3 C3 MOL 1 16.417 14.732 0.663 1.00 0.00
ATOM 4 C4 MOL 1 18.496 15.366 -0.471 1.00 0.00
ATOM 5 C5 MOL 1 17.015 13.567 -1.482 1.00 0.00
ATOM 6 C6 MOL 1 15.693 15.779 0.018 1.00 0.00
ATOM 7 C7 MOL 1 15.307 13.777 1.020 1.00 0.00
ATOM 8 C8 MOL 1 16.942 15.313 2.010 1.00 0.00
ATOM 9 C9 MOL 1 17.646 16.451 -1.361 1.00 0.00
ATOM 10 N10 MOL 1 19.019 15.899 0.861 1.00 0.00
ATOM 11 C11 MOL 1 15.959 12.473 -1.196 1.00 0.00
ATOM 12 C12 MOL 1 14.403 15.799 0.518 1.00 0.00
ATOM 13 C13 MOL 1 16.179 16.645 -0.862 1.00 0.00
ATOM 14 O14 MOL 1 14.159 14.689 1.403 1.00 0.00
ATOM 15 C15 MOL 1 14.899 12.986 -0.210 1.00 0.00
ATOM 16 C16 MOL 1 17.969 16.420 1.747 1.00 0.00
ATOM 17 C17 MOL 1 20.056 16.927 0.663 1.00 0.00
ATOM 18 C18 MOL 1 13.566 16.775 0.184 1.00 0.00
ATOM 19 C19 MOL 1 15.281 17.721 -1.321 1.00 0.00
ATOM 20 O20 MOL 1 13.720 12.646 -0.346 1.00 0.00
ATOM 21 C21 MOL 1 21.259 16.286 0.008 1.00 0.00
ATOM 22 O22 MOL 1 12.278 16.816 0.702 1.00 0.00
ATOM 23 C23 MOL 1 14.040 17.798 -0.803 1.00 0.00
ATOM 24 C24 MOL 1 22.410 16.944 -0.094 1.00 0.00
ATOM 25 H25 MOL 1 19.357 15.031 -1.060 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>

Naltrexone
<jmol>
<jmolApplet>
<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Thu Oct 26 11:49:10 GMT Standard Time 2006
ATOM 1 O1 MOL 1 17.558 13.998 -0.496 1.00 0.00
ATOM 2 C2 MOL 1 17.076 15.115 0.248 1.00 0.00
ATOM 3 C3 MOL 1 17.258 16.394 -0.557 1.00 0.00
ATOM 4 C4 MOL 1 15.561 15.011 0.531 1.00 0.00
ATOM 5 C5 MOL 1 17.860 15.228 1.589 1.00 0.00
ATOM 6 C6 MOL 1 16.778 17.574 0.073 1.00 0.00
ATOM 7 C7 MOL 1 18.653 16.799 -0.879 1.00 0.00
ATOM 8 C8 MOL 1 16.508 16.294 -1.921 1.00 0.00
ATOM 9 C9 MOL 1 15.127 16.315 1.434 1.00 0.00
ATOM 10 N10 MOL 1 14.843 14.899 -0.812 1.00 0.00
ATOM 11 C11 MOL 1 19.354 15.543 1.336 1.00 0.00
ATOM 12 C12 MOL 1 17.493 18.660 -0.426 1.00 0.00
ATOM 13 C13 MOL 1 15.791 17.648 0.954 1.00 0.00
ATOM 14 O14 MOL 1 18.548 18.231 -1.333 1.00 0.00
ATOM 15 C15 MOL 1 19.467 16.754 0.400 1.00 0.00
ATOM 16 C16 MOL 1 15.014 16.064 -1.686 1.00 0.00
ATOM 17 C17 MOL 1 13.406 14.609 -0.651 1.00 0.00
ATOM 18 C18 MOL 1 17.129 19.900 -0.114 1.00 0.00
ATOM 19 C19 MOL 1 15.387 18.995 1.400 1.00 0.00
ATOM 20 O20 MOL 1 20.317 17.624 0.613 1.00 0.00
ATOM 21 C21 MOL 1 13.178 13.073 -0.836 1.00 0.00
ATOM 22 O22 MOL 1 17.801 20.995 -0.638 1.00 0.00
ATOM 23 C23 MOL 1 16.014 20.069 0.881 1.00 0.00
ATOM 24 C24 MOL 1 11.870 12.702 -0.129 1.00 0.00
ATOM 25 C25 MOL 1 13.234 12.318 0.500 1.00 0.00
ATOM 26 H26 MOL 1 19.132 16.101 -1.579 1.00 0.00
ATOM 27 H27 MOL 1 15.339 14.101 1.101 1.00 0.00
TER</inlineContents>
</jmolApplet>
</jmol>

Both naloxone and naltrexone are competitive antagonists at the μ- and κ-opioid receptors, and to a lesser extent at δ-opioid receptors. The blockade of these receptors is what prevents the opiods such as morphine, from combining with these receptor sites thus preventing the side effects usually caused by morphine.

==Derrivatives of Morphine==

Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:
<br>
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]
|[[Image:codeine.gif]]
|[[Image:heroin.gif]]
|-
|align="left" colspan="3" bgcolor="white"|Morphine
|Codeine
|Heroine
|-
|}
<br>
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br>
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br>
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.

<br>
Click on the thumbnail to view the enlarged synthesis of codeine from morphine.
[[Image:codeine_s.gif|thumb|Synthesis of Codeine]]

==References and External Links==
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine
*Morphine, Molecule of the Month
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]
*Schmitz J, Stotts A, Rhoades H, Grabowski J. "Naltrexone and relapse prevention treatment for cocaine-dependent patients.". Addict Behav 26 (2): 167-80. PMID 11316375.
*Chicago Recovery Alliance's naloxone distrobution project

It:Morphine

2006-10-26T11:36:20Z

Sv205: /* Pharmacology of Morphine */

It:Morphine

2006-10-26T11:28:50Z

Sv205: /* Pharmacology of Morphine */

It:Morphine

2006-10-26T10:41:42Z

Sv205: pharmacology

It:Morphine

2006-10-25T13:47:17Z

Sv205: /* Derrivatives of Morphine */

It:Morphine

2006-10-25T13:43:11Z

Sv205:

It:sitagliptin page

2006-10-24T13:32:43Z

Sv205:

==Sitagliptin ( Januvia <sup>tm</sup> )==
'''Brief Definition :'''
Sitagliptin is a relatively new drug (''Approved by FDA 17/10/2006'') used for treating type 2 Diabetes '''Diabetes Mellitus'''.

[[User:Rih05|Rih05]] 19:45, 19 October 2006 (BST)

{{Chem-Data|
| ImageFile = work_icon
| IUPACName = Sitagliptin
| OtherNames = Sitagliptin, Januvia
| Abbreviations =
| Formula =
| MolarMass =
| CASNo =
| Density =
| Solubility =
| MeltingPt =
| BoilingPt =
| pKa =
| pKb =
| IsoelectricPt =
| DeltaHf =
| DeltaHc =
| EINECS =
| PubChem =
| SMILES = C
| InChI =
}}
{{Chem-Data_Properties|
Density = 34
}}

==3D Structure of Sitagliptin==

<jmol>
<jmolApplet>
<size>300</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Tue Oct 24 14:17:29 GMT Standard Time 2006
ATOM 1 C1 MOL 1 24.957 10.890 0.016 1.00 0.00
ATOM 2 F2 MOL 1 26.264 11.134 0.388 1.00 0.00
ATOM 3 F3 MOL 1 24.944 10.366 -1.258 1.00 0.00
ATOM 4 F4 MOL 1 24.365 9.961 0.849 1.00 0.00
ATOM 5 C5 MOL 1 24.174 12.186 0.005 1.00 0.00
ATOM 6 N6 MOL 1 22.802 12.351 -0.016 1.00 0.00
ATOM 7 N7 MOL 1 24.712 13.343 0.019 1.00 0.00
ATOM 8 C8 MOL 1 22.591 13.676 -0.008 1.00 0.00
ATOM 9 C9 MOL 1 21.763 11.357 -0.082 1.00 0.00
ATOM 10 N10 MOL 1 23.710 14.285 0.011 1.00 0.00
ATOM 11 C11 MOL 1 21.250 14.327 -0.014 1.00 0.00
ATOM 12 C12 MOL 1 20.441 11.943 0.520 1.00 0.00
ATOM 13 N13 MOL 1 20.176 13.311 -0.004 1.00 0.00
ATOM 14 C14 MOL 1 18.820 13.806 -0.170 1.00 0.00
ATOM 15 C15 MOL 1 17.591 12.930 0.007 1.00 0.00
ATOM 16 O16 MOL 1 18.664 14.997 -0.458 1.00 0.00
ATOM 17 C17 MOL 1 16.321 13.848 -0.031 1.00 0.00
ATOM 18 C18 MOL 1 15.023 12.995 0.095 1.00 0.00
ATOM 19 N19 MOL 1 16.405 14.808 1.088 1.00 0.00
ATOM 20 C20 MOL 1 13.730 13.831 0.050 1.00 0.00
ATOM 21 C21 MOL 1 12.552 13.207 0.060 1.00 0.00
ATOM 22 C22 MOL 1 13.757 15.304 -0.005 1.00 0.00
ATOM 23 F23 MOL 1 12.509 11.868 0.106 1.00 0.00
ATOM 24 C24 MOL 1 11.299 13.977 0.019 1.00 0.00
ATOM 25 C25 MOL 1 12.621 16.000 -0.036 1.00 0.00
ATOM 26 C26 MOL 1 11.334 15.307 -0.025 1.00 0.00
ATOM 27 F27 MOL 1 12.656 17.338 -0.077 1.00 0.00
ATOM 28 F28 MOL 1 10.190 16.014 -0.062 1.00 0.00
TER</inlineContents>
</jmolApplet>
</jmol>

==2D Structure of Sitagliptin==

[[Image:2d_sitagliptin.GIF]]

File:2d sitagliptin.GIF

2006-10-24T13:30:46Z

Sv205:

It:sitagliptin page

2006-10-24T13:22:37Z

Sv205:

File:Sitagliptin.pdb

2006-10-24T13:13:34Z

Sv205:

It:Morphine

2006-10-24T10:58:47Z

Sv205:

==Introduction to Morphine==

Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects suc as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.

==3D Structure of Morphine==

<jmol>
<jmolApplet>
<size>300</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>

==2D Structure of Morphine==

[[Image:200px-Morphine-2D-skeletal.GIF]]

==Uses==

Morphine is used legally:

*analgesic in hospital settings for
*Pain after surgery
*Pain associated with trauma
*In the relief of severe chronic pain
*Cancer pain
*Pain from kidney stones
*Back pain
*In epidural anesthesia
*As an antitussive for severe cough
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS)
*To relieve breathlessness in patients in respiratory failure

==References and External Links==
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine
*Morphine, Molecule of the Month

It:Morphine

2006-10-24T10:50:24Z

Sv205:

==Introduction to Morphine==

Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects suc as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.

==3D Structure of Morphine==

<jmol>
<jmolApplet>
<size>300</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>

==2D Structure of Morphine==

[[Image:200px-Morphine-2D-skeletal.GIF]]

==References and External Links==
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine
*Morphine, Molecule of the Month

It:Morphine

2006-10-24T10:45:28Z

Sv205:

File:200px-Morphine-2D-skeletal.GIF

2006-10-24T10:43:37Z

Sv205:

File:Morphine.png

2006-10-24T10:25:54Z

Sv205:

File:Morphine 2d.png

2006-10-24T10:23:09Z

Sv205:

It:Morphine

2006-10-24T10:17:40Z

Sv205:

It:Morphine

2006-10-23T15:35:52Z

Sv205: 3d image

==Introduction to Morphine==

Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects suc as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.

==3D Structure of Morphine==

<jmol>
<jmolApplet>
<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>

File:Morphine.pdb

2006-10-23T15:26:05Z

Sv205:

It:Morphine

2006-10-23T15:18:38Z

Sv205: introduction to morphine

It:Methoxsalen

2006-10-23T15:04:49Z

Sv205:

==3D Structure of Methoxsalen==
<jmol>
<jmolApplet>
<size>300</size>
<color>black</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Fri Oct 20 13:03:31 GMT Standard Time 2006
ATOM 1 O1 MOL 1 14.448 14.733 -0.004 1.00 0.00
ATOM 2 C2 MOL 1 13.218 15.463 -0.005 1.00 0.00
ATOM 3 C3 MOL 1 14.316 13.321 -0.005 1.00 0.00
ATOM 4 C4 MOL 1 15.435 12.588 -0.004 1.00 0.00
ATOM 5 C5 MOL 1 13.014 12.603 -0.000 1.00 0.00
ATOM 6 C6 MOL 1 15.358 11.104 -0.005 1.00 0.00
ATOM 7 O7 MOL 1 16.680 13.257 -0.003 1.00 0.00
ATOM 8 C8 MOL 1 12.982 11.296 -0.003 1.00 0.00
ATOM 9 O9 MOL 1 11.700 13.147 0.007 1.00 0.00
ATOM 10 C10 MOL 1 14.176 10.484 -0.006 1.00 0.00
ATOM 11 C11 MOL 1 16.569 10.328 -0.000 1.00 0.00
ATOM 12 C12 MOL 1 17.826 12.419 0.004 1.00 0.00
ATOM 13 C13 MOL 1 11.646 10.851 0.002 1.00 0.00
ATOM 14 C14 MOL 1 10.895 11.955 0.009 1.00 0.00
ATOM 15 C15 MOL 1 17.740 10.951 0.005 1.00 0.00
ATOM 16 O16 MOL 1 18.946 12.942 0.010 1.00 0.00
TER
</inlineContents>
</jmolApplet>
</jmol>

<br>
----
<br>
<font color=red><font size=5>What is Methoxsalen?</font color></font size><br><br>
<font color=brown>''3D structure of Methoxsalen:''</font><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
ATOM 1 C 0 -0.431 2.805 -0.885 0.00 0.00 C+0
ATOM 2 O 0 -0.438 2.207 0.412 0.00 0.00 O+0
ATOM 3 C 0 -0.497 0.861 0.225 0.00 0.00 C+0
ATOM 4 C 0 0.674 0.124 0.113 0.00 0.00 C+0
ATOM 5 C 0 0.612 -1.271 -0.081 0.00 0.00 C+0
ATOM 6 C 0 -0.622 -1.915 -0.162 0.00 0.00 C+0
ATOM 7 C 0 -1.789 -1.170 -0.049 0.00 0.00 C+0
ATOM 8 C 0 -1.731 0.223 0.151 0.00 0.00 C+0
ATOM 9 O 0 -3.003 0.668 0.221 0.00 0.00 O+0
ATOM 10 C 0 -3.875 -0.345 0.080 0.00 0.00 C+0
ATOM 11 C 0 -3.220 -1.501 -0.084 0.00 0.00 C+0
ATOM 12 C 0 1.862 -2.029 -0.197 0.00 0.00 C+0
ATOM 13 C 0 3.034 -1.350 -0.112 0.00 0.00 C+0
ATOM 14 C 0 3.023 0.048 0.083 0.00 0.00 C+0
ATOM 15 O 0 4.083 0.644 0.158 0.00 0.00 O+0
ATOM 16 O 0 1.877 0.737 0.189 0.00 0.00 O+0
ATOM 17 H 0 0.438 2.454 -1.442 0.00 0.00 H+0
ATOM 18 H 0 -1.340 2.528 -1.418 0.00 0.00 H+0
ATOM 19 H 0 -0.384 3.889 -0.786 0.00 0.00 H+0
ATOM 20 H 0 -0.671 -2.984 -0.311 0.00 0.00 H+0
ATOM 21 H 0 -4.950 -0.242 0.100 0.00 0.00 H+0
ATOM 22 H 0 -3.656 -2.480 -0.222 0.00 0.00 H+0
ATOM 23 H 0 1.851 -3.098 -0.346 0.00 0.00 H+0
ATOM 24 H 0 3.973 -1.878 -0.193 0.00 0.00 H+0
CONECT 1 2 17 18 19 NONE 29
CONECT 2 1 3 0 0 NONE 30
CONECT 3 2 8 4 0 NONE 31
CONECT 4 3 16 5 0 NONE 32
CONECT 5 4 6 12 0 NONE 33
CONECT 6 5 7 20 0 NONE 34
CONECT 7 6 11 8 0 NONE 35
CONECT 8 7 3 9 0 NONE 36
CONECT 9 8 10 0 0 NONE 37
CONECT 10 9 11 21 0 NONE 38
CONECT 11 10 7 22 0 NONE 39
CONECT 12 5 13 23 0 NONE 40
CONECT 13 12 14 24 0 NONE 41
CONECT 14 13 15 16 0 NONE 42
CONECT 15 14 0 0 0 NONE 43
CONECT 16 14 4 0 0 NONE 44
END</inlineContents>
</jmolApplet>
</jmol><br>

<font color=brown>''2D structure of Methoxsalen:''</font><br><br>
[[Image:methox.gif|middle|2D structure of Methoxsalen]]
<br><br>

{| border="1"
|+ '''- Physical & Chemical properties<sup>1</sup> -'''
! Chemical name
| 9-methoxy-7H-furo[3,2-g][1]-benzopyran-7-one
|-
! Molecular formular
|C<sub>12</sub>H<sub>8</sub>O<sub>4</sub>
|-
! Molecular weight
| 216.19 g/mol
|-
! State
| Solid
|-
! Appearance
| White to yellow powder
|-
! Solubility
| Clear to very slightly hazy yellow solution at 200mg plus 4ml of chloroform
|-
! Elemental analysis
| 65.3 - 68.0% Carbon
|-
! Purity by gas chromatography
| Not less than 98%
|}
<br>
<font color=brown>''FT NMR of Methoxsalen:''</font><br><br>
[[Image:nmr.JPG|middle|FT NMR of Methoxsalen]]

Methoxsalen is a naturally occurring photoactive substance found in the seeds of the Ammi majus (Umbelliferae) plant. It belongs to a group of compounds known as psoralens or furocoumarins. It is a photoactive substance and produces its effects when exposed to ultraviolet (UVA) light. Methoxsalen causes damage to the DNA of cells, ultimately causing their death<sup>2</sup>.
<br>
<br>
<font color=red><font size=5>What is Methoxsalen used for?</font color></font size><br>
<br>
Methoxsalen is used along with ultraviolet light (found in sunlight and some special lamps) in a treatment called psoralen plus ultraviolet light A (PUVA) to treat vitiligo, a disease in which skin color is lost<sup>3</sup>.<br>
Methoxsalen selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content of DNA correlates with the degree of Methoxsalen-induced cross-linking, meaning after activation it binds preferentially to the guanine and cytosine bases of DNA, leading its cross-linking, thus inhibiting DNA synthesis and function. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed.<br>
It is also a drug that has been clinically proven to decrease smoking by interacting with and blocking the action of a protein that breaks down nicotine<sup>4</sup>. People who have nicotine addiction continue to smoke to maintain high nicotine levels in the brain. Methoxsalen specifically prevents the protein cytochrome P450 2A6 from degrading nicotine. Cytochrome P450 2A6 also breaks down carcinogens found in tobacco to more harmful chemicals that can cause cancer.

<font color=red><font size=5>References</font color></font size><br><br>
1)[http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIAL/M3501 2006 Sigma-Aldrich Co]<br>
2)[http://www.ufscc.ufl.edu/Patient/drug_dictionary.aspx?id=791 University of Florida Shands Cancer Center]<br>
3)[http://www.drugs.com Drugs information online]<br>
4)[http://www.medicalnewstoday.com/medicalnews.php?newsid=28864 Medical News Today]<br>

It:Retinal

2006-10-23T14:59:02Z

Sv205:

__toc__

'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.

== Structure of Cis-Retinal ==

{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" bgcolor="lt blue"|'''2D Structure'''
| align="center" bgcolor="lt blue"|'''3D Structure'''
|-
| [[image:Cis-RetinalSo.gif]]
|<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 54
CONECT 2 1 3 4 0 NONE 55
CONECT 4 2 5 6 0 NONE 56
CONECT 6 4 7 11 0 NONE 57
CONECT 7 6 8 9 10 NONE 58
CONECT 11 6 12 13 0 NONE 59
CONECT 13 11 14 15 0 NONE 60
CONECT 15 13 16 17 0 NONE 61
CONECT 17 15 18 22 0 NONE 62
CONECT 18 17 19 20 21 NONE 63
CONECT 22 17 23 24 0 NONE 64
CONECT 24 22 25 26 0 NONE 65
CONECT 26 24 41 27 0 NONE 66
CONECT 27 26 28 32 0 NONE 67
CONECT 28 27 29 30 31 NONE 68
CONECT 32 27 33 34 35 NONE 69
CONECT 35 32 36 37 38 NONE 70
CONECT 38 35 39 40 41 NONE 71
CONECT 41 38 26 42 46 NONE 72
CONECT 42 41 43 44 45 NONE 73
CONECT 46 41 47 48 49 NONE 74
END NONE 75
NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|}

== Properties of Cis-Retinal ==

{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|(11Z)-retinal
|-
| Chemical formula
| align="center"|C<sub>20</sub>H<sub>28</sub>O
|-
| Molecular mass
| align="center"|284 g/mol
|-
| align="center" colspan="3" bgcolor="white" |'''Physical properties'''
|-
| Melting point
| align="center"|... °C
|-
| Boiling point
| align="center"|... °C
|-
| Appearance
| align="center"|...
|-
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous'''
|-
| SMILES
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1
|-
|}

==Structure of all-trans retinal==
'''2D Structure'''

[[Image:AllTransRetinal.gif]]

==Properties of all-trans retinal==

==The role of retinal in the vision process==

The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.

[[Image:RetinalConversion.png]]

==Synthesis of Rhodopsin==
[[Image:Synthesis_of_rhodopsin.gif]]

== References ==

*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH

*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0.
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.

File:Synthesis of rhodopsin.gif

2006-10-23T14:54:34Z

Sv205:

It:Retinal

2006-10-23T14:54:04Z

Sv205: role of retinal in vision

__toc__

'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.

== Structure of Cis-Retinal ==

{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" bgcolor="lt blue"|'''2D Structure'''
| align="center" bgcolor="lt blue"|'''3D Structure'''
|-
| [[image:Cis-RetinalSo.gif]]
|<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 54
CONECT 2 1 3 4 0 NONE 55
CONECT 4 2 5 6 0 NONE 56
CONECT 6 4 7 11 0 NONE 57
CONECT 7 6 8 9 10 NONE 58
CONECT 11 6 12 13 0 NONE 59
CONECT 13 11 14 15 0 NONE 60
CONECT 15 13 16 17 0 NONE 61
CONECT 17 15 18 22 0 NONE 62
CONECT 18 17 19 20 21 NONE 63
CONECT 22 17 23 24 0 NONE 64
CONECT 24 22 25 26 0 NONE 65
CONECT 26 24 41 27 0 NONE 66
CONECT 27 26 28 32 0 NONE 67
CONECT 28 27 29 30 31 NONE 68
CONECT 32 27 33 34 35 NONE 69
CONECT 35 32 36 37 38 NONE 70
CONECT 38 35 39 40 41 NONE 71
CONECT 41 38 26 42 46 NONE 72
CONECT 42 41 43 44 45 NONE 73
CONECT 46 41 47 48 49 NONE 74
END NONE 75
NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|}

== Properties of Cis-Retinal ==

{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|(11Z)-retinal
|-
| Chemical formula
| align="center"|C<sub>20</sub>H<sub>28</sub>O
|-
| Molecular mass
| align="center"|284 g/mol
|-
| align="center" colspan="3" bgcolor="white" |'''Physical properties'''
|-
| Melting point
| align="center"|... °C
|-
| Boiling point
| align="center"|... °C
|-
| Appearance
| align="center"|...
|-
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous'''
|-
| SMILES
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1
|-
|}

==Structure of all-trans retinal==
'''2D Structure'''

[[Image:AllTransRetinal.gif]]

==Properties of all-trans retinal==

==The role of retinal in the vision process==

The molecule that takes part in the vision process is rhodopsin which consists of 11-cis retinal and protein opsin. Retinal is a Vitamin A derivative. When there is no light present the 11-cis retinal has a bent configuration and is attached to the retinal molecule in a stable arrangement. When light strikes the retina, the retinal molecule absorbs a photon into one of the pi-bonds between the 11th and 12th carbon atoms, hence the 11 cis retinal is transfformed into the all trans retinal.

[[Image:RetinalConversion.png]]

== References ==

*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH

*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0.
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.

It:Retinal

2006-10-23T14:38:06Z

Sv205: added references to scheme from person who stole it off wikipedia

'''Retinal''' (aka: retinaldehyde or retinene<sub>1</sub>) is the most important molecule associated with vision. Retinal changes structure when it is exposed to light, essentially transferring the energy from the light it absorbs to an electrical impulse in the retina of the eye, which is then passed along the optic nerve to the central nervous system to be processed. All vision systems operate in this manner, so Retinal is resposible for all vision. Retinal is a retinine molecule that exists as two different isomers - 11-cis retinal and all-trans retinal.
__toc__
== Structure of Cis-Retinal ==

{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" bgcolor="lt blue"|'''2D Structure'''
| align="center" bgcolor="lt blue"|'''3D Structure'''
|-
| [[image:Cis-RetinalSo.gif]]
|<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 54
CONECT 2 1 3 4 0 NONE 55
CONECT 4 2 5 6 0 NONE 56
CONECT 6 4 7 11 0 NONE 57
CONECT 7 6 8 9 10 NONE 58
CONECT 11 6 12 13 0 NONE 59
CONECT 13 11 14 15 0 NONE 60
CONECT 15 13 16 17 0 NONE 61
CONECT 17 15 18 22 0 NONE 62
CONECT 18 17 19 20 21 NONE 63
CONECT 22 17 23 24 0 NONE 64
CONECT 24 22 25 26 0 NONE 65
CONECT 26 24 41 27 0 NONE 66
CONECT 27 26 28 32 0 NONE 67
CONECT 28 27 29 30 31 NONE 68
CONECT 32 27 33 34 35 NONE 69
CONECT 35 32 36 37 38 NONE 70
CONECT 38 35 39 40 41 NONE 71
CONECT 41 38 26 42 46 NONE 72
CONECT 42 41 43 44 45 NONE 73
CONECT 46 41 47 48 49 NONE 74
END NONE 75
NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|}

== Properties of Cis-Retinal ==

{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|(11Z)-retinal
|-
| Chemical formula
| align="center"|C<sub>20</sub>H<sub>28</sub>O
|-
| Molecular mass
| align="center"|284 g/mol
|-
| align="center" colspan="3" bgcolor="white" |'''Physical properties'''
|-
| Melting point
| align="center"|... °C
|-
| Boiling point
| align="center"|... °C
|-
| Appearance
| align="center"|...
|-
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous'''
|-
| SMILES
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1
|-
|}

==Structure of all-trans retinal==
'''2D Structure'''

[[Image:AllTransRetinal.gif]]

==Properties of all-trans retinal==

==How is Retinal affected by the absorption of light?==

The absorption of light causes the pi-bond to break allowing the molecule to rotate. This allows the retinal molecule to change shape. The new shape of the molecule affects the shape of the protein to which the retinal molecule is attached to. This process occurs via a signal that passes along the optic nerve.

[[Image:RetinalConversion.png]]

== References ==

*Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH

*1.Chang, Raymond (1998). Chemistry, 6th Ed.. New York: McGraw Hill. ISBN 0-07-115221-0.
*2. Feynman, Richard (1985). QED - The Strange Theory of Light and Matter. Princeton, New Jersey: Princeton University Press. ISBN 0691024170.

File:Synthesis,svk.gif

2006-10-23T14:31:09Z

Sv205:

It:Retinal

2006-10-23T13:33:54Z

Sv205:

== Structure of Cis-Retinal ==

{| class="toccolours" border="0" style="fix: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" bgcolor="lt blue"|'''2D Structure'''
| align="center" bgcolor="lt blue"|'''3D Structure'''
|-
| [[image:Cis-RetinalSo.gif]]
|<jmol>
<jmolApplet>
<size>400</size>
<color>white</color>
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER NONAME 20-Oct-06 NONE 1
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 -4.284 3.090 -0.370 0.00 0.00 O+0
ATOM 2 C 0 -4.565 2.093 0.267 0.00 0.00 C+0
ATOM 3 H 0 -5.014 2.185 1.244 0.00 0.00 H+0
ATOM 4 C 0 -4.301 0.826 -0.264 0.00 0.00 C+0
ATOM 5 H 0 -3.848 0.734 -1.240 0.00 0.00 H+0
ATOM 6 C 0 -4.620 -0.304 0.458 0.00 0.00 C+0
ATOM 7 C 0 -5.252 -0.175 1.820 0.00 0.00 C+0
ATOM 8 H 0 -5.510 -1.165 2.196 0.00 0.00 H+0
ATOM 9 H 0 -4.549 0.302 2.503 0.00 0.00 H+0
ATOM 10 H 0 -6.155 0.431 1.745 0.00 0.00 H+0
ATOM 11 C 0 -4.356 -1.571 -0.074 0.00 0.00 C+0
ATOM 12 H 0 -5.156 -2.288 -0.184 0.00 0.00 H+0
ATOM 13 C 0 -3.075 -1.905 -0.455 0.00 0.00 C+0
ATOM 14 H 0 -2.888 -2.841 -0.961 0.00 0.00 H+0
ATOM 15 C 0 -2.013 -1.030 -0.187 0.00 0.00 C+0
ATOM 16 H 0 -2.209 -0.062 0.250 0.00 0.00 H+0
ATOM 17 C 0 -0.732 -1.401 -0.480 0.00 0.00 C+0
ATOM 18 C 0 -0.460 -2.751 -1.091 0.00 0.00 C+0
ATOM 19 H 0 0.617 -2.905 -1.166 0.00 0.00 H+0
ATOM 20 H 0 -0.895 -3.529 -0.463 0.00 0.00 H+0
ATOM 21 H 0 -0.903 -2.796 -2.086 0.00 0.00 H+0
ATOM 22 C 0 0.332 -0.523 -0.212 0.00 0.00 C+0
ATOM 23 H 0 0.148 0.407 0.306 0.00 0.00 H+0
ATOM 24 C 0 1.593 -0.845 -0.603 0.00 0.00 C+0
ATOM 25 H 0 1.769 -1.745 -1.174 0.00 0.00 H+0
ATOM 26 C 0 2.679 0.001 -0.262 0.00 0.00 C+0
ATOM 27 C 0 2.629 1.266 -0.646 0.00 0.00 C+0
ATOM 28 C 0 1.416 1.729 -1.413 0.00 0.00 C+0
ATOM 29 H 0 0.676 2.124 -0.718 0.00 0.00 H+0
ATOM 30 H 0 1.708 2.509 -2.116 0.00 0.00 H+0
ATOM 31 H 0 0.989 0.888 -1.959 0.00 0.00 H+0
ATOM 32 C 0 3.711 2.266 -0.361 0.00 0.00 C+0
ATOM 33 H 0 4.301 2.427 -1.263 0.00 0.00 H+0
ATOM 34 H 0 3.259 3.209 -0.052 0.00 0.00 H+0
ATOM 35 C 0 4.621 1.753 0.756 0.00 0.00 C+0
ATOM 36 H 0 4.080 1.760 1.702 0.00 0.00 H+0
ATOM 37 H 0 5.501 2.391 0.833 0.00 0.00 H+0
ATOM 38 C 0 5.048 0.319 0.417 0.00 0.00 C+0
ATOM 39 H 0 5.449 0.286 -0.595 0.00 0.00 H+0
ATOM 40 H 0 5.809 -0.013 1.124 0.00 0.00 H+0
ATOM 41 C 0 3.817 -0.587 0.519 0.00 0.00 C+0
ATOM 42 C 0 3.414 -0.733 1.988 0.00 0.00 C+0
ATOM 43 H 0 3.178 0.249 2.399 0.00 0.00 H+0
ATOM 44 H 0 2.538 -1.377 2.062 0.00 0.00 H+0
ATOM 45 H 0 4.238 -1.173 2.549 0.00 0.00 H+0
ATOM 46 C 0 4.155 -1.967 -0.050 0.00 0.00 C+0
ATOM 47 H 0 4.922 -2.436 0.566 0.00 0.00 H+0
ATOM 48 H 0 3.260 -2.589 -0.051 0.00 0.00 H+0
ATOM 49 H 0 4.524 -1.859 -1.070 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 54
CONECT 2 1 3 4 0 NONE 55
CONECT 4 2 5 6 0 NONE 56
CONECT 6 4 7 11 0 NONE 57
CONECT 7 6 8 9 10 NONE 58
CONECT 11 6 12 13 0 NONE 59
CONECT 13 11 14 15 0 NONE 60
CONECT 15 13 16 17 0 NONE 61
CONECT 17 15 18 22 0 NONE 62
CONECT 18 17 19 20 21 NONE 63
CONECT 22 17 23 24 0 NONE 64
CONECT 24 22 25 26 0 NONE 65
CONECT 26 24 41 27 0 NONE 66
CONECT 27 26 28 32 0 NONE 67
CONECT 28 27 29 30 31 NONE 68
CONECT 32 27 33 34 35 NONE 69
CONECT 35 32 36 37 38 NONE 70
CONECT 38 35 39 40 41 NONE 71
CONECT 41 38 26 42 46 NONE 72
CONECT 42 41 43 44 45 NONE 73
CONECT 46 41 47 48 49 NONE 74
END NONE 75
NONE 70
</inlineContents>
</jmolApplet>
</jmol>
|}

== Properties of Cis-Retinal ==

{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
|-
| align="center" colspan="3" bgcolor="lt blue"|'''General properties'''
|-
| Chemical name
| align="center"|(11Z)-retinal
|-
| Chemical formula
| align="center"|C<sub>20</sub>H<sub>28</sub>O
|-
| Molecular mass
| align="center"|284 g/mol
|-
| align="center" colspan="3" bgcolor="white" |'''General properties'''
|-
| Melting point
| align="center"|... °C
|-
| Boiling point
| align="center"|...
|-
| align="center" colspan="3" bgcolor="white" |'''Miscelleneous'''
|-
| SMILES
| align="center"|CC1(C)C(/C=C/C(C)=C/C=C\C(C)=C\C=O)=C(C)CCC1
|-
|}

==How is Retinal affected by the absorption of light?==

The absorption of light causes the pi-bond to break allowing the molecule to rotate. This allows the retinal molecule to change shape. The new shape of the molecule affects the shape of the protein to which the retinal molecule is attached to. This process occurs via a signal that passes along the optic nerve.

== References ==

1. Beilstein Data: Copyright (c) 1988-2006, Beilstein institut zur Foerderung der Chemischen Wissenschaften licensed to Beilstein GmBH and MDL information systems GmbH

It:Methoxsalen

2006-10-20T12:11:09Z

Sv205:

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<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>REMARK MSI WebLab Viewer PDB file
REMARK Created: Fri Oct 20 13:03:31 GMT Standard Time 2006
ATOM 1 O1 MOL 1 14.448 14.733 -0.004 1.00 0.00
ATOM 2 C2 MOL 1 13.218 15.463 -0.005 1.00 0.00
ATOM 3 C3 MOL 1 14.316 13.321 -0.005 1.00 0.00
ATOM 4 C4 MOL 1 15.435 12.588 -0.004 1.00 0.00
ATOM 5 C5 MOL 1 13.014 12.603 -0.000 1.00 0.00
ATOM 6 C6 MOL 1 15.358 11.104 -0.005 1.00 0.00
ATOM 7 O7 MOL 1 16.680 13.257 -0.003 1.00 0.00
ATOM 8 C8 MOL 1 12.982 11.296 -0.003 1.00 0.00
ATOM 9 O9 MOL 1 11.700 13.147 0.007 1.00 0.00
ATOM 10 C10 MOL 1 14.176 10.484 -0.006 1.00 0.00
ATOM 11 C11 MOL 1 16.569 10.328 -0.000 1.00 0.00
ATOM 12 C12 MOL 1 17.826 12.419 0.004 1.00 0.00
ATOM 13 C13 MOL 1 11.646 10.851 0.002 1.00 0.00
ATOM 14 C14 MOL 1 10.895 11.955 0.009 1.00 0.00
ATOM 15 C15 MOL 1 17.740 10.951 0.005 1.00 0.00
ATOM 16 O16 MOL 1 18.946 12.942 0.010 1.00 0.00
TER
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It:Lignocaine

2006-10-20T11:54:58Z

Sv205:

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<size>200</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>REMARK MSI WebLab Viewer PDB file
REMARK Created: Fri Oct 20 12:51:30 GMT Standard Time 2006
ATOM 1 N1 MOL 1 16.171 14.259 -0.113 1.00 0.00
ATOM 2 C2 MOL 1 15.015 15.193 -0.048 1.00 0.00
ATOM 3 C3 MOL 1 16.350 12.740 -0.084 1.00 0.00
ATOM 4 C4 MOL 1 13.631 14.760 0.341 1.00 0.00
ATOM 5 O5 MOL 1 15.239 16.388 -0.269 1.00 0.00
ATOM 6 C6 MOL 1 17.620 12.369 0.089 1.00 0.00
ATOM 7 C7 MOL 1 15.303 11.593 -0.240 1.00 0.00
ATOM 8 N8 MOL 1 12.525 15.630 -0.076 1.00 0.00
ATOM 9 C9 MOL 1 18.684 13.420 0.225 1.00 0.00
ATOM 10 C10 MOL 1 18.006 10.961 0.175 1.00 0.00
ATOM 11 C11 MOL 1 13.855 11.750 -0.564 1.00 0.00
ATOM 12 C12 MOL 1 15.713 10.329 -0.151 1.00 0.00
ATOM 13 C13 MOL 1 11.298 14.808 0.242 1.00 0.00
ATOM 14 C14 MOL 1 12.596 16.947 0.673 1.00 0.00
ATOM 15 C15 MOL 1 17.099 9.998 0.079 1.00 0.00
ATOM 16 C16 MOL 1 9.983 15.249 -0.446 1.00 0.00
ATOM 17 C17 MOL 1 11.626 18.047 0.168 1.00 0.00
TER
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