ChemWiki - User contributions [en]

It:Mustard Gas

2006-12-06T19:06:25Z

Raj105:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Mustard Gas
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Mustard Gas.png|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>

<jmolApplet>
<size>250</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>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 04-Dec-06 0 NONE 4
ATOM 1 Cl 0 -4.089 0.584 -0.000 0.00 0.00 Cl+0
ATOM 2 C 0 -2.708 -0.575 0.000 0.00 0.00 C+0
ATOM 3 C 0 -1.390 0.202 -0.000 0.00 0.00 C+0
ATOM 4 S 0 0.000 -0.964 0.000 0.00 0.00 S+0
ATOM 5 C 0 1.390 0.202 -0.000 0.00 0.00 C+0
ATOM 6 C 0 2.708 -0.575 0.000 0.00 0.00 C+0
ATOM 7 Cl 0 4.089 0.584 -0.000 0.00 0.00 Cl+0
ATOM 8 H 0 -2.759 -1.202 0.890 0.00 0.00 H+0
ATOM 9 H 0 -2.759 -1.202 -0.890 0.00 0.00 H+0
ATOM 10 H 0 -1.338 0.829 -0.890 0.00 0.00 H+0
ATOM 11 H 0 -1.338 0.829 0.890 0.00 0.00 H+0
ATOM 12 H 0 1.338 0.829 -0.890 0.00 0.00 H+0
ATOM 13 H 0 1.338 0.829 0.890 0.00 0.00 H+0
ATOM 14 H 0 2.759 -1.202 0.890 0.00 0.00 H+0
ATOM 15 H 0 2.759 -1.202 -0.890 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 20
CONECT 2 1 3 8 9 NONE 21
CONECT 3 2 4 10 11 NONE 22
CONECT 4 3 5 0 0 NONE 23
CONECT 5 4 6 12 13 NONE 24
CONECT 6 5 7 14 15 NONE 25
CONECT 7 6 0 0 0 NONE 26
END NONE 27
</inlineContents>
</jmolApplet>
</jmol>

|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Chemical Names]]
| colspan="2"| 1,1-thiobis(2-chloroethane)
bis(2-chloroethyl) [35S]sulfide

[35S]sulfur mustard
|-
| [[Other Names]]
|colspan="2"| Mustard Gas
|-
| [[Chemical formula|Molecular formula]]
| colspan="2" | C<sub>4</sub>H<sub>8</sub>Cl<sub>2</sub>S
|-
| [[Molar mass]]
| colspan="2" |157.97 g/mol
|-
| [[Beilstein Registry Number]]
| colspan="2" | 8137686
|-
| [[Appearance]]
| colspan="2" | Odourless and Colourless gas (when pure)
|-
! {{chembox header}} colspan="3"| Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| colspan="2" | 1.27 g/cm<sup>3
|-
| [[Solubility]] in [[Water_(molecule)|water (ph=7)]]
| colspan="2" | 0.06% at 20 °C
|-
| [[Melting point]]
| colspan="2" | 14 °C
|-
| [[Boiling point]]
| colspan="2" | 217 °C
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br/>[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
==Introduction==
{|
| Mustard gas is a colourless, odourless gas. It gets its common name from the fact that in its impure form it smells similar to The first reported use of the gas was in 1860 by Frederick Guthrie, (shown right) a Professor at the Royal School of Mines and founding member of the Institute of Physics. He reported the toxic effects that mustard gas had on his skin, including reddening and blistering.|| [[image:Frederick Guthrie.JPG]]
|}

==History==
Mustard gas was first used as a chemical weapon in the First World War when it was used to dehabilite the opposing army due to the fact that it could penetrate all known masks and protective clothing used at that time.
It has been used as a chemical weapon in various other conflicts since then, most recently in 1988 in Iraq, though it may also have been used throughout the 1990's.

==Synthesis==
Frederick Guthrie synthesised mustard gas simply by reacting ethene with sulphur dichloride. However, the chemical supplier Bayer AG developed a synthesis during the First World War by which mustard gas can be produced on a mass scale by reacting thiodiglycol with hydrochloric acid.

==Chemistry==
Mustard gas can undergo intramolecular displacement of a chloride ion to form a three-membered cyclic sulphonium ion, (as shown below,) via an SN2 mechanism. Nucleophilic attack on the ion can occur, reacting either with water or proteins in the skin. Mustard gas can react twice in this way as it has two chloride ions that it can lose. Also, having a sulphur atom in the chain causes the SN2 reaction to go much faster than if it was just a straight hydrocarbon chain.

[[image:new reaction scheme.png]]

===Physicological Effects===
Mustard gas is a blister agent that causes pain and irritation to the skin and eyes, however the symptons of exposure only become apparent between two and twenty four hours after the attack. It is known as a blister agent because it causes water blisters on the body of a person who has been exposed to it. This is because despite the fact that mustard gas isn't very soluble in water it is very soluble in fat which means it can be absorbed quickly by the skin. Mustards attack the corneas and lead to blindness, if it is inhaled, it will cause the lining of the lungs to blister which can cause chronic impairment or death. It is possible to treat exposure to mustard gas by detoxification with either sulphur amines, magnesium monoperoxyphthalate or peroxy acids.
Exposure to mustard gas can result in permanant disability, cancers or, if more than fifty percent of the body is exposed to mustard, death.

===Nitrogen Mustards===
{|
| Nitrogen mustards are compounds that are similar to other mustards where the sulphur is replaced by a nitrogen. These compounds, despite the fact that they're also blister agents and are a cause of cancer can be used to treat Hodgekin's Lymphona.|| [[image:Nitrogen Mustard.png]]
|}

===Disposal===
Mustard gas used to be disposed of by being dumped into the sea which has caused severe problems because the mustard polymerises on contact with the water. This has lead to continued cases of mustard exposure because the polymerised compound can be brought to the surface of the sea by fishing nets. In particular this occurs in Sweden where mustard gas was dumped into the water after the Second World War.
Burying mustard gas also creates problems and the gas has been found to still be in the soil ten years after burying. This occurs especially in areas where there is little water in the soil. The mustard gas reacts with the water to form an intermediate sulphonium ion. This sulphonium ion then reacts further with the water to form a stable sulphonium ion that forms a ''protective layer'' around the mustard preventing the rest of it from reacting.

==References==
http://physicsweb.org/articles/world/12/11/10/1/pw-12-11-10fig1

http://www.chm.bris.ac.uk/motm/mustard/mustard2.htm

http://en.wikipedia.org/wiki/Mustard_gas

http://www.opcw.org/resp/html/mustard.html

Jonathan Claydon, Nick Greeves et al, ''Organic Chemistry,'' Oxford University Press, '''2001,''' p1258.

http://en.wikipedia.org/wiki/Nitrogen_mustard

http://en.wikipedia.org/wiki/Blister_agent

File:New reaction scheme.png

2006-12-06T19:05:56Z

Raj105:

File:Reaction scheme.png

2006-12-06T19:02:19Z

Raj105:

It:Mustard Gas

2006-12-06T18:56:24Z

Raj105:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Mustard Gas
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Mustard Gas.png|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>

<jmolApplet>
<size>250</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>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 04-Dec-06 0 NONE 4
ATOM 1 Cl 0 -4.089 0.584 -0.000 0.00 0.00 Cl+0
ATOM 2 C 0 -2.708 -0.575 0.000 0.00 0.00 C+0
ATOM 3 C 0 -1.390 0.202 -0.000 0.00 0.00 C+0
ATOM 4 S 0 0.000 -0.964 0.000 0.00 0.00 S+0
ATOM 5 C 0 1.390 0.202 -0.000 0.00 0.00 C+0
ATOM 6 C 0 2.708 -0.575 0.000 0.00 0.00 C+0
ATOM 7 Cl 0 4.089 0.584 -0.000 0.00 0.00 Cl+0
ATOM 8 H 0 -2.759 -1.202 0.890 0.00 0.00 H+0
ATOM 9 H 0 -2.759 -1.202 -0.890 0.00 0.00 H+0
ATOM 10 H 0 -1.338 0.829 -0.890 0.00 0.00 H+0
ATOM 11 H 0 -1.338 0.829 0.890 0.00 0.00 H+0
ATOM 12 H 0 1.338 0.829 -0.890 0.00 0.00 H+0
ATOM 13 H 0 1.338 0.829 0.890 0.00 0.00 H+0
ATOM 14 H 0 2.759 -1.202 0.890 0.00 0.00 H+0
ATOM 15 H 0 2.759 -1.202 -0.890 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 20
CONECT 2 1 3 8 9 NONE 21
CONECT 3 2 4 10 11 NONE 22
CONECT 4 3 5 0 0 NONE 23
CONECT 5 4 6 12 13 NONE 24
CONECT 6 5 7 14 15 NONE 25
CONECT 7 6 0 0 0 NONE 26
END NONE 27
</inlineContents>
</jmolApplet>
</jmol>

|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Chemical Names]]
| colspan="2"| 1,1-thiobis(2-chloroethane)
bis(2-chloroethyl) [35S]sulfide

[35S]sulfur mustard
|-
| [[Other Names]]
|colspan="2"| Mustard Gas
|-
| [[Chemical formula|Molecular formula]]
| colspan="2" | C<sub>4</sub>H<sub>8</sub>Cl<sub>2</sub>S
|-
| [[Molar mass]]
| colspan="2" |157.97 g/mol
|-
| [[Beilstein Registry Number]]
| colspan="2" | 8137686
|-
| [[Appearance]]
| colspan="2" | Odourless and Colourless gas (when pure)
|-
! {{chembox header}} colspan="3"| Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| colspan="2" | 1.27 g/cm<sup>3
|-
| [[Solubility]] in [[Water_(molecule)|water (ph=7)]]
| colspan="2" | 0.06% at 20 °C
|-
| [[Melting point]]
| colspan="2" | 14 °C
|-
| [[Boiling point]]
| colspan="2" | 217 °C
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br/>[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
==Introduction==
{|
| Mustard gas is a colourless, odourless gas. It gets its common name from the fact that in its impure form it smells similar to The first reported use of the gas was in 1860 by Frederick Guthrie, (shown right) a Professor at the Royal School of Mines and founding member of the Institute of Physics. He reported the toxic effects that mustard gas had on his skin, including reddening and blistering.|| [[image:Frederick Guthrie.JPG]]
|}

==History==
Mustard gas was first used as a chemical weapon in the First World War when it was used to dehabilite the opposing army due to the fact that it could penetrate all known masks and protective clothing used at that time.
It has been used as a chemical weapon in various other conflicts since then, most recently in 1988 in Iraq, though it may also have been used throughout the 1990's.

==Synthesis==
Frederick Guthrie synthesised mustard gas simply by reacting ethene with sulphur dichloride. However, the chemical supplier Bayer AG developed a synthesis during the First World War by which mustard gas can be produced on a mass scale by reacting thiodiglycol with hydrochloric acid.

==Chemistry==
Mustard gas can undergo intramolecular displacement of a chloride ion to form a three-membered cyclic sulphonium ion, (as shown below,) via an SN2 mechanism. Nucleophilic attack on the ion can occur, reacting either with water or proteins in the skin. Mustard gas can react twice in this way as it has two chloride ions that it can lose. Also, having a sulphur atom in the chain causes the SN2 reaction to go much faster than if it was just a straight hydrocarbon chain.

===Physicological Effects===
Mustard gas is a blister agent that causes pain and irritation to the skin and eyes, however the symptons of exposure only become apparent between two and twenty four hours after the attack. It is known as a blister agent because it causes water blisters on the body of a person who has been exposed to it. This is because despite the fact that mustard gas isn't very soluble in water it is very soluble in fat which means it can be absorbed quickly by the skin. Mustards attack the corneas and lead to blindness, if it is inhaled, it will cause the lining of the lungs to blister which can cause chronic impairment or death. It is possible to treat exposure to mustard gas by detoxification with either sulphur amines, magnesium monoperoxyphthalate or peroxy acids.
Exposure to mustard gas can result in permanant disability, cancers or, if more than fifty percent of the body is exposed to mustard, death.

===Nitrogen Mustards===
{|
| Nitrogen mustards are compounds that are similar to other mustards where the sulphur is replaced by a nitrogen. These compounds, despite the fact that they're also blister agents and are a cause of cancer can be used to treat Hodgekin's Lymphona.|| [[image:Nitrogen Mustard.png]]
|}

===Disposal===
Mustard gas used to be disposed of by being dumped into the sea which has caused severe problems because the mustard polymerises on contact with the water. This has lead to continued cases of mustard exposure because the polymerised compound can be brought to the surface of the sea by fishing nets. In particular this occurs in Sweden where mustard gas was dumped into the water after the Second World War.
Burying mustard gas also creates problems and the gas has been found to still be in the soil ten years after burying. This occurs especially in areas where there is little water in the soil. The mustard gas reacts with the water to form an intermediate sulphonium ion. This sulphonium ion then reacts further with the water to form a stable sulphonium ion that forms a ''protective layer'' around the mustard preventing the rest of it from reacting.

==References==
http://physicsweb.org/articles/world/12/11/10/1/pw-12-11-10fig1

http://www.chm.bris.ac.uk/motm/mustard/mustard2.htm

http://en.wikipedia.org/wiki/Mustard_gas

http://www.opcw.org/resp/html/mustard.html

Jonathan Claydon, Nick Greeves et al, ''Organic Chemistry,'' Oxford University Press, '''2001,''' p1258.

http://en.wikipedia.org/wiki/Nitrogen_mustard

http://en.wikipedia.org/wiki/Blister_agent

File:Nitrogen Mustard.png

2006-12-06T18:53:14Z

Raj105:

It:Mustard Gas

2006-12-06T18:27:09Z

Raj105:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Mustard Gas
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Mustard Gas.png|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>

<jmolApplet>
<size>250</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>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 04-Dec-06 0 NONE 4
ATOM 1 Cl 0 -4.089 0.584 -0.000 0.00 0.00 Cl+0
ATOM 2 C 0 -2.708 -0.575 0.000 0.00 0.00 C+0
ATOM 3 C 0 -1.390 0.202 -0.000 0.00 0.00 C+0
ATOM 4 S 0 0.000 -0.964 0.000 0.00 0.00 S+0
ATOM 5 C 0 1.390 0.202 -0.000 0.00 0.00 C+0
ATOM 6 C 0 2.708 -0.575 0.000 0.00 0.00 C+0
ATOM 7 Cl 0 4.089 0.584 -0.000 0.00 0.00 Cl+0
ATOM 8 H 0 -2.759 -1.202 0.890 0.00 0.00 H+0
ATOM 9 H 0 -2.759 -1.202 -0.890 0.00 0.00 H+0
ATOM 10 H 0 -1.338 0.829 -0.890 0.00 0.00 H+0
ATOM 11 H 0 -1.338 0.829 0.890 0.00 0.00 H+0
ATOM 12 H 0 1.338 0.829 -0.890 0.00 0.00 H+0
ATOM 13 H 0 1.338 0.829 0.890 0.00 0.00 H+0
ATOM 14 H 0 2.759 -1.202 0.890 0.00 0.00 H+0
ATOM 15 H 0 2.759 -1.202 -0.890 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 20
CONECT 2 1 3 8 9 NONE 21
CONECT 3 2 4 10 11 NONE 22
CONECT 4 3 5 0 0 NONE 23
CONECT 5 4 6 12 13 NONE 24
CONECT 6 5 7 14 15 NONE 25
CONECT 7 6 0 0 0 NONE 26
END NONE 27
</inlineContents>
</jmolApplet>
</jmol>

|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Chemical Names]]
| colspan="2"| 1,1-thiobis(2-chloroethane)
bis(2-chloroethyl) [35S]sulfide

[35S]sulfur mustard
|-
| [[Other Names]]
|colspan="2"| Mustard Gas
|-
| [[Chemical formula|Molecular formula]]
| colspan="2" | C<sub>4</sub>H<sub>8</sub>Cl<sub>2</sub>S
|-
| [[Molar mass]]
| colspan="2" |157.97 g/mol
|-
| [[Beilstein Registry Number]]
| colspan="2" | 8137686
|-
| [[Appearance]]
| colspan="2" | Odourless and Colourless gas (when pure)
|-
! {{chembox header}} colspan="3"| Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| colspan="2" | 1.27 g/cm<sup>3
|-
| [[Solubility]] in [[Water_(molecule)|water (ph=7)]]
| colspan="2" | 0.06% at 20 °C
|-
| [[Melting point]]
| colspan="2" | 14 °C
|-
| [[Boiling point]]
| colspan="2" | 217 °C
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br/>[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
==Introduction==
{|
| Mustard gas is a colourless, odourless gas. It gets its common name from the fact that in its impure form it smells similar to The first reported use of the gas was in 1860 by Frederick Guthrie, (shown right) a Professor at the Royal School of Mines and founding member of the Institute of Physics. He reported the toxic effects that mustard gas had on his skin, including reddening and blistering.|| [[image:Frederick Guthrie.JPG]]
|}

==History==
Mustard gas was first used as a chemical weapon in the First World War when it was used to dehabilite the opposing army due to the fact that it could penetrate all known masks and protective clothing used at that time.
It has been used as a chemical weapon in various other conflicts since then, most recently in 1988 in Iraq, though it may also have been used throughout the 1990's.

==Synthesis==
Frederick Guthrie synthesised mustard gas simply by reacting ethene with sulphur dichloride. However, the chemical supplier Bayer AG developed a synthesis during the First World War by which mustard gas can be produced on a mass scale by reacting thiodiglycol with hydrochloric acid.

==Chemistry==
Mustard gas can undergo intramolecular displacement of a chloride ion to form a three-membered cyclic sulphonium ion, (as shown below,) via an SN2 mechanism. Nucleophilic attack on the ion can occur, reacting either with water or proteins in the skin. Mustard gas can react twice in this way as it has two chloride ions that it can lose. Also, having a sulphur atom in the chain causes the SN2 reaction to go much faster than if it was just a straight hydrocarbon chain.

===Physicological Effects===
Mustard gas is a blister agent that causes pain and irritation to the skin and eyes, however the symptons of exposure only become apparent between two and twenty four hours after the attack. It is known as a blister agent because it causes water blisters on the body of a person who has been exposed to it. This is because despite the fact that mustard gas isn't very soluble in water it is very soluble in fat which means it can be absorbed quickly by the skin. Mustards attack the corneas and lead to blindness, if it is inhaled, it will cause the lining of the lungs to blister which can cause chronic impairment or death. It is possible to treat exposure to mustard gas by detoxification with either sulphur amines, magnesium monoperoxyphthalate or peroxy acids.
Exposure to mustard gas can result in permanant disability, cancers or, if more than fifty percent of the body is exposed to mustard, death.

===Nitrogen Mustards===
Nitrogen mustards are compounds that are similar to other mustards where the sulphur is replaced by a nitrogen. These compounds, despite the fact that they're also blister agents and are a cause of cancer can be used to treat Hodgekin's Lymphona.

===Disposal===
Mustard gas used to be disposed of by being dumped into the sea which has caused severe problems because the mustard polymerises on contact with the water. This has lead to continued cases of mustard exposure because the polymerised compound can be brought to the surface of the sea by fishing nets. In particular this occurs in Sweden where mustard gas was dumped into the water after the Second World War.
Burying mustard gas also creates problems and the gas has been found to still be in the soil ten years after burying. This occurs especially in areas where there is little water in the soil. The mustard gas reacts with the water to form an intermediate sulphonium ion. This sulphonium ion then reacts further with the water to form a stable sulphonium ion that forms a ''protective layer'' around the mustard preventing the rest of it from reacting.

==References==
http://physicsweb.org/articles/world/12/11/10/1/pw-12-11-10fig1

http://www.chm.bris.ac.uk/motm/mustard/mustard2.htm

http://en.wikipedia.org/wiki/Mustard_gas

http://www.opcw.org/resp/html/mustard.html

Jonathan Claydon, Nick Greeves et al, ''Organic Chemistry,'' Oxford University Press, '''2001,''' p1258.

http://en.wikipedia.org/wiki/Nitrogen_mustard

http://en.wikipedia.org/wiki/Blister_agent

It:Mustard Gas

2006-12-06T17:30:41Z

Raj105:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Mustard Gas
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Mustard Gas.png|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>

<jmolApplet>
<size>250</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>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 04-Dec-06 0 NONE 4
ATOM 1 Cl 0 -4.089 0.584 -0.000 0.00 0.00 Cl+0
ATOM 2 C 0 -2.708 -0.575 0.000 0.00 0.00 C+0
ATOM 3 C 0 -1.390 0.202 -0.000 0.00 0.00 C+0
ATOM 4 S 0 0.000 -0.964 0.000 0.00 0.00 S+0
ATOM 5 C 0 1.390 0.202 -0.000 0.00 0.00 C+0
ATOM 6 C 0 2.708 -0.575 0.000 0.00 0.00 C+0
ATOM 7 Cl 0 4.089 0.584 -0.000 0.00 0.00 Cl+0
ATOM 8 H 0 -2.759 -1.202 0.890 0.00 0.00 H+0
ATOM 9 H 0 -2.759 -1.202 -0.890 0.00 0.00 H+0
ATOM 10 H 0 -1.338 0.829 -0.890 0.00 0.00 H+0
ATOM 11 H 0 -1.338 0.829 0.890 0.00 0.00 H+0
ATOM 12 H 0 1.338 0.829 -0.890 0.00 0.00 H+0
ATOM 13 H 0 1.338 0.829 0.890 0.00 0.00 H+0
ATOM 14 H 0 2.759 -1.202 0.890 0.00 0.00 H+0
ATOM 15 H 0 2.759 -1.202 -0.890 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 20
CONECT 2 1 3 8 9 NONE 21
CONECT 3 2 4 10 11 NONE 22
CONECT 4 3 5 0 0 NONE 23
CONECT 5 4 6 12 13 NONE 24
CONECT 6 5 7 14 15 NONE 25
CONECT 7 6 0 0 0 NONE 26
END NONE 27
</inlineContents>
</jmolApplet>
</jmol>

|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Chemical Names]]
| colspan="2"| 1,1-thiobis(2-chloroethane)
bis(2-chloroethyl) [35S]sulfide

[35S]sulfur mustard
|-
| [[Other Names]]
|colspan="2"| Mustard Gas
|-
| [[Chemical formula|Molecular formula]]
| colspan="2" | C<sub>4</sub>H<sub>8</sub>Cl<sub>2</sub>S
|-
| [[Molar mass]]
| colspan="2" |157.97 g/mol
|-
| [[Beilstein Registry Number]]
| colspan="2" | 8137686
|-
| [[Appearance]]
| colspan="2" | Odourless and Colourless gas (when pure)
|-
! {{chembox header}} colspan="3"| Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| colspan="2" | 1.27 g/cm<sup>3
|-
| [[Solubility]] in [[Water_(molecule)|water (ph=7)]]
| colspan="2" | 0.06% at 20 °C
|-
| [[Melting point]]
| colspan="2" | 14 °C
|-
| [[Boiling point]]
| colspan="2" | 217 °C
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br/>[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
==Introduction==
{|
| Mustard gas is a colourless, odourless gas. It gets its common name from the fact that in its impure form it smells similar to The first reported use of the gas was in 1860 by Frederick Guthrie, (shown right) a Professor at the Royal School of Mines and founding member of the Institute of Physics. He reported the toxic effects that mustard gas had on his skin, including reddening and blistering.|| [[image:Frederick Guthrie.JPG]]
|}

==History==
Mustard gas was first used as a chemical weapon in the First World War when it was used to dehabilite the opposing army due to the fact that it could penetrate all known masks and protective clothing used at that time.
It has been used as a chemical weapon in various other conflicts since then, most recently in 1988 in Iraq, though it may also have been used throughout the 1990's.

==Synthesis==
Frederick Guthrie synthesised mustard gas simply by reacting ethene with sulphur dichloride. However, the chemical supplier Bayer AG developed a synthesis during the First World War by which mustard gas can be produced on a mass scale by reacting thiodiglycol with hydrochloric acid.

==Chemistry==
Mustard gas can undergo intramolecular displacement of a chloride ion to form a three-membered cyclic sulphonium ion, (as shown below,) via an SN2 mechanism. Nucleophilic attack on the ion can occur, reacting either with water or proteins in the skin. Mustard gas can react twice in this way as it has two chloride ions that it can lose. Also, having a sulphur atom in the chain causes the SN2 reaction to go much faster than if it was just a straight hydrocarbon chain.

===Physicological Effects===
Mustard gas is a blister agent that causes pain and irritation to the skin and eyes, however the symptons of exposure only become apparent between two and twenty four hours after the attack. It is known as a blister agent because it causes water blisters on the body of a person who has been exposed to it. This is because despite the fact that mustard gas isn't very soluble in water it is very soluble in fat which means it can be absorbed quickly by the skin. Mustards attack the corneas and lead to blindness, if it is inhaled, it will cause the lining of the lungs to blister which can cause chronic impairment or death. It is possible to treat exposure to mustard gas by detoxification with either sulphur amines, magnesium monoperoxyphthalate or peroxy acids.
Exposure to mustard gas can result in permanant disability, cancers or, if more than fifty percent of the body is exposed to mustard, death.
===Nitrogen Mustards===
Nitrogen mustards are compounds that are similar to other mustards where the sulphur is replaced by a nitrogen. These compounds, despite the fact that they're also blister agents and are a cause of cancer can be used to treat Hodgekin's Lymphona.

==References==
http://physicsweb.org/articles/world/12/11/10/1/pw-12-11-10fig1

http://www.chm.bris.ac.uk/motm/mustard/mustard.htm

http://en.wikipedia.org/wiki/Mustard_gas

http://www.opcw.org/resp/html/mustard.html

Jonathan Claydon, Nick Greeves et al, ''Organic Chemistry,'' Oxford University Press, '''2001,''' p1258.

http://en.wikipedia.org/wiki/Nitrogen_mustard

http://en.wikipedia.org/wiki/Blister_agent

It:Mustard Gas

2006-12-06T16:13:27Z

Raj105:

It:Mustard Gas

2006-12-04T16:09:10Z

Raj105:

It:Mustard Gas

2006-12-04T15:43:34Z

Raj105:

It:Mustard Gas

2006-12-04T15:31:06Z

Raj105:

It:Mustard Gas

2006-12-04T15:17:10Z

Raj105:

It:Mustard Gas

2006-12-04T15:10:45Z

Raj105:

It:Mustard Gas

2006-12-04T14:38:26Z

Raj105:

Mustard gas was first synthesised in 1860 by Frederick Guthrie, (shown below) a Professor at the Royal School of Mines. [[image:Frederick Guthrie.JPG]]

[[image:Mustard Gas.png]]

<jmol>
<jmolApplet>
<size>250</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>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 04-Dec-06 0 NONE 4
ATOM 1 Cl 0 -4.089 0.584 -0.000 0.00 0.00 Cl+0
ATOM 2 C 0 -2.708 -0.575 0.000 0.00 0.00 C+0
ATOM 3 C 0 -1.390 0.202 -0.000 0.00 0.00 C+0
ATOM 4 S 0 0.000 -0.964 0.000 0.00 0.00 S+0
ATOM 5 C 0 1.390 0.202 -0.000 0.00 0.00 C+0
ATOM 6 C 0 2.708 -0.575 0.000 0.00 0.00 C+0
ATOM 7 Cl 0 4.089 0.584 -0.000 0.00 0.00 Cl+0
ATOM 8 H 0 -2.759 -1.202 0.890 0.00 0.00 H+0
ATOM 9 H 0 -2.759 -1.202 -0.890 0.00 0.00 H+0
ATOM 10 H 0 -1.338 0.829 -0.890 0.00 0.00 H+0
ATOM 11 H 0 -1.338 0.829 0.890 0.00 0.00 H+0
ATOM 12 H 0 1.338 0.829 -0.890 0.00 0.00 H+0
ATOM 13 H 0 1.338 0.829 0.890 0.00 0.00 H+0
ATOM 14 H 0 2.759 -1.202 0.890 0.00 0.00 H+0
ATOM 15 H 0 2.759 -1.202 -0.890 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 20
CONECT 2 1 3 8 9 NONE 21
CONECT 3 2 4 10 11 NONE 22
CONECT 4 3 5 0 0 NONE 23
CONECT 5 4 6 12 13 NONE 24
CONECT 6 5 7 14 15 NONE 25
CONECT 7 6 0 0 0 NONE 26
END NONE 27
</inlineContents>
</jmolApplet>
</jmol>

===Sources===
http://physicsweb.org/articles/world/12/11/10/1/pw-12-11-10fig1

It:Mustard Gas

2006-12-04T14:31:13Z

Raj105:

File:Mustard Gas.png

2006-12-04T14:28:42Z

Raj105:

It:Mustard Gas

2006-12-04T14:12:05Z

Raj105:

Mustard gas was first synthesised in 1860 by Frederick Guthrie, (shown below) a Professor at the Royal School of Mines. [[image:Frederick Guthrie.JPG]]

===Sources===
http://physicsweb.org/articles/world/12/11/10/1/pw-12-11-10fig1

It:Mustard Gas

2006-12-04T14:07:12Z

Raj105:

Mustard gas was first synthesised in 1860 by Frederick Guthrie, a Professor at the Royal School of Mines.

[[Image:{name}|{type}|{location}|{size}|{caption}]] or more specifically
[[Image:Frederick Guthrie.jpg|thumb|right|200|Frederick Guthrie]]

===Sources===
http://physicsweb.org/articles/world/12/11/10/1/pw-12-11-10fig1

File:Frederick Guthrie.JPG

2006-12-04T11:57:54Z

Raj105:

File:First person to synthesis mustard gas.doc

2006-12-04T11:53:32Z

Raj105: Frederick Guthrie

Frederick Guthrie

It:projects

2006-12-04T11:44:25Z

Raj105: /* Supplemental Project Page */

__FORCETOC__

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'''Please do not edit this page itself'''. Click on one of the titles to start editing.
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! bgcolor="cyan" |Project<br /> Number
! bgcolor="cyan" |General Keywords
|-
| bgcolor="#CCFF00" |01
| bgcolor="#CCFF00" | [[it:Lignocaine|Lignocaine (used in dentistry as a "local")]]
|-
| bgcolor="#CCFF00" |02
| bgcolor="#66FF99" | [[it:Piperine|Piperine (active ingredient of both black and white pepper)]]
|-
| bgcolor="#CCFF00" |03
| bgcolor="#CCFF00" | [[it:Rapamycin|Rapamycin (prevents transplant rejection)]]
|-
| bgcolor="#CCFF00" |04
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|-
| bgcolor="#CCFF00" |05
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|-
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|-
| bgcolor="#CCFF00" |07
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|-
| bgcolor="#CCFF00" |08
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|-
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|-
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|-
| bgcolor="#CCFF00" |11
| bgcolor="#CCFF00" | [[it:Sibutramine|Sibutramine (appetite suppresor)]]
|-
| bgcolor="#CCFF00" |12
| bgcolor="#66FF99" | [[it:Anandamide|Anandamide (the "feel-good" factor in chocolate)]]
|-
| bgcolor="#CCFF00" |13
| bgcolor="#CCFF00" | [[it:h3nbh3|Ammonia-borane: H<sub>3</sub>N-BH<sub>3</sub> (Hydrogen storage molecule?)]]
|-
| bgcolor="#CCFF00" |14
| bgcolor="#66FF99" | [[it:Methoxsalen|Methoxsalen (Treatment of psoriasis)]]
|-
| bgcolor="#CCFF00" |15
| bgcolor="#CCFF00" | [[it:Hycocine|Hyoscine (From Mandrake and Witches Henbane, pre-med before surgery)]]
|-
| bgcolor="#CCFF00" |16
| bgcolor="#66FF99" | [[it:Capreomycin|Capreomycin (Drug-resistant TB)]]
|-
| bgcolor="#CCFF00" |17
| bgcolor="#CCFF00" | [[it:wilkinson|Wilkinson's catalyst]]
|-
| bgcolor="#CCFF00" |18
| bgcolor="#66FF99" | [[it:Jacobsen|Jacobsen's epoxidation catalyst]]
|-
| bgcolor="#CCFF00" |19
| bgcolor="#CCFF00" | [[it:Methylaluminoxane|Methylaluminoxane: MAO - hugely important ethylene polymerisation cocatalyst]]
|-
| bgcolor="#CCFF00" |20
| bgcolor="#66FF99" | [[it:Schwartz|Schwartz reagent for the hydrozirconation of alkenes and alkynes]]
|-
| bgcolor="#CCFF00" |21
| bgcolor="#CCFF00" | [[it:Schrock|Schrock metathesis catalyst]]
|-
| bgcolor="#CCFF00" |22
| bgcolor="#66FF99" | [[it:knots|Molecular-scale knots (nanoscale devices)]]
|-
|bgcolor="#CCFF00" |23
| bgcolor="#CCFF00" | [[it:Vioxx|Vioxx (treatment of osteoarthritis symptoms and pain)]]
|-
| bgcolor="#CCFF00" |24
| bgcolor="#66FF99" | [[it:Sertraline|Sertraline HCl (anti-depression)]]
|-
| bgcolor="#CCFF00" |25
| bgcolor="#CCFF00" | [[it:Ceftriaxone|Ceftriaxone (Gonorrhoea)]]
|-
| bgcolor="#CCFF00" |26
| bgcolor="#66FF99" | [[it:Zithromycin|Zithromycin (anti-infective)]]
|-
| bgcolor="#CCFF00" |27
| bgcolor="#CCFF00" | [[it:Lipitor|Lipitor (Cholesterol reducing agent)]]
|-
| bgcolor="#CCFF00" |28
| bgcolor="#66FF99" | [[it:Cyameluric Acid|Cyameluric acid (Linus Pauling's last idea!)]]
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*This will produce the effect: [[it:name_of_project|Descriptive name of intended project]]
----
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*[[it:Retinal|Retinal, molecule of sight]]
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*[[it:Morphine|Morphine, painkiller]]
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*[[it:Tryptophan|Tryptophan]]
*[[it:methylpentynol|methylpentynol, tranquilliser.]]
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*[[it:Scopolamine|Scopolamine, the (Former) Truth Drug]]
*[[it:Camptothecin|Camptothecin,Anti-cancer agent ]]
*[[it:Salmeterol|Salmeterol, an agonist used to treat asthma]]
*[[it:Psilocin|Psilocin]]
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*[[it:Polyurethane|Polyurethane]]
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*[[it:Mustard Gas|Mustard Gas]]

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----
--[[User:Rzepa|Rzepa]] 12:25, 19 October 2006 (BST)--[[User:Rzepa|Rzepa]] 08:31, 5 November 2006 (UTC)

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

[[Template:Drug-Box]] - For pharmaceutical drugs just copy variable names and code generates tables

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[[R & S Phrases]]

It:Hycocine

2006-10-24T14:42:49Z

Raj105: /* '''HYOSCINE''' */

== '''HYOSCINE''' ==

{| border="1"
|+ '''Essential Data'''
|-
! Formula
| C1<sub>7</sub>H<sub>21</sub>NO<sub>4</sub>
|-
! Molecular weight
| 303.35
|-
! Melting point
| 59<sup>o</sup>C
|-
|}

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Hyoscine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:hyoscine.gif|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>300</size>
<color>black</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>hyoscine.pdb
title1
title2
ATOM 1 O 0 1.207 -1.433 0.214 0.00 0.00 O+0
ATOM 2 C 0 0.876 -0.299 0.465 0.00 0.00 C+0
ATOM 3 C 0 1.906 0.801 0.481 0.00 0.00 C+0
ATOM 4 H 0 1.934 1.258 1.470 0.00 0.00 H+0
ATOM 5 C 0 1.538 1.860 -0.560 0.00 0.00 C+0
ATOM 6 O 0 0.310 2.488 -0.187 0.00 0.00 O+0
ATOM 7 C 0 3.260 0.226 0.155 0.00 0.00 C+0
ATOM 8 C 0 4.294 0.333 1.066 0.00 0.00 C+0
ATOM 9 C 0 5.537 -0.195 0.767 0.00 0.00 C+0
ATOM 10 C 0 5.745 -0.830 -0.443 0.00 0.00 C+0
ATOM 11 C 0 4.710 -0.938 -1.354 0.00 0.00 C+0
ATOM 12 C 0 3.467 -0.414 -1.053 0.00 0.00 C+0
ATOM 13 O 0 -0.411 -0.017 0.723 0.00 0.00 O+0
ATOM 14 C 0 -1.401 -1.072 0.702 0.00 0.00 C+0
ATOM 15 C 0 -2.545 -0.794 1.661 0.00 0.00 C+0
ATOM 16 C 0 -3.763 -0.158 0.995 0.00 0.00 C+0
ATOM 17 C 0 -3.374 1.193 0.361 0.00 0.00 C+0
ATOM 18 O 0 -2.043 1.394 -0.100 0.00 0.00 O+0
ATOM 19 C 0 -2.916 0.830 -1.072 0.00 0.00 C+0
ATOM 20 C 0 -3.097 -0.697 -1.157 0.00 0.00 C+0
ATOM 21 C 0 -1.825 -1.419 -0.715 0.00 0.00 C+0
ATOM 22 N 0 -4.153 -1.012 -0.158 0.00 0.00 N+0
ATOM 23 C 0 -5.413 -0.472 -0.683 0.00 0.00 C+0
ATOM 24 H 0 2.328 2.610 -0.611 0.00 0.00 H+0
ATOM 25 H 0 1.423 1.387 -1.535 0.00 0.00 H+0
ATOM 26 H 0 0.114 3.146 -0.868 0.00 0.00 H+0
ATOM 27 H 0 4.132 0.829 2.012 0.00 0.00 H+0
ATOM 28 H 0 6.345 -0.111 1.479 0.00 0.00 H+0
ATOM 29 H 0 6.715 -1.242 -0.677 0.00 0.00 H+0
ATOM 30 H 0 4.873 -1.434 -2.299 0.00 0.00 H+0
ATOM 31 H 0 2.659 -0.498 -1.764 0.00 0.00 H+0
ATOM 32 H 0 -0.877 -1.978 1.099 0.00 0.00 H+0
ATOM 33 H 0 -2.851 -1.736 2.139 0.00 0.00 H+0
ATOM 34 H 0 -2.190 -0.131 2.463 0.00 0.00 H+0
ATOM 35 H 0 -4.596 -0.043 1.701 0.00 0.00 H+0
ATOM 36 H 0 -4.015 2.055 0.564 0.00 0.00 H+0
ATOM 37 H 0 -3.213 1.426 -1.941 0.00 0.00 H+0
ATOM 38 H 0 -3.406 -1.008 -2.165 0.00 0.00 H+0
ATOM 39 H 0 -1.011 -1.164 -1.408 0.00 0.00 H+0
ATOM 40 H 0 -1.985 -2.503 -0.790 0.00 0.00 H+0
ATOM 41 H 0 -5.637 -0.940 -1.642 0.00 0.00 H+0
ATOM 42 H 0 -6.219 -0.681 0.020 0.00 0.00 H+0
ATOM 43 H 0 -5.319 0.606 -0.818 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 48
CONECT 2 1 3 13 0 NONE 49
CONECT 3 2 4 5 7 NONE 50
CONECT 5 3 6 24 25 NONE 51
CONECT 6 5 26 0 0 NONE 52
CONECT 7 3 12 8 0 NONE 53
CONECT 8 7 9 27 0 NONE 54
CONECT 9 8 10 28 0 NONE 55
CONECT 10 9 11 29 0 NONE 56
CONECT 11 10 12 30 0 NONE 57
CONECT 12 11 7 31 0 NONE 58
CONECT 13 2 14 0 0 NONE 59
CONECT 14 13 21 15 32 NONE 60
CONECT 15 14 16 33 34 NONE 61
CONECT 16 15 22 17 35 NONE 62
CONECT 17 16 18 19 36 NONE 63
CONECT 18 17 19 0 0 NONE 64
CONECT 19 17 18 20 37 NONE 65
CONECT 20 19 21 22 38 NONE 66
CONECT 21 20 14 39 40 NONE 67
CONECT 22 20 16 23 0 NONE 68
CONECT 23 22 41 42 43 NONE 69
M END</inlineContents>
</jmolApplet>
</jmol>
|}

Hyoscine is a drug thst is more commonly known as Scopolamine. It is a '''tropane alkaloid drug''' which means that it contains a '''tropane''' group; containing the chemical formula C<sub>8</sub>H<sub>15</sub>N (as drawn below).

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 150; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
title1
title2
27 28 0 0 0 0 0 0 0 0999 V2000
2.1160 0.8000 -0.9900 C 0 0 0 0 0 0 0 0 0 1
0.7240 0.3840 -0.7690 N 0 0 0 0 0 0 0 0 0 2
0.2550 1.0950 0.4350 C 0 0 2 0 0 0 0 0 0 3
0.3930 0.1090 1.5790 C 0 0 0 0 0 0 0 0 0 4
1.3010 -1.0180 0.9950 C 0 0 0 0 0 0 0 0 0 5
0.7540 -1.0820 -0.4900 C 0 0 1 0 0 0 0 0 0 6
-0.6900 -1.5800 -0.1550 C 0 0 0 0 0 0 0 0 0 7
-1.7130 -0.7250 -0.8310 C 0 0 0 0 0 0 0 0 0 8
-2.0800 0.3870 0.1310 C 0 0 0 0 0 0 0 0 0 9
-1.1790 1.5800 0.0800 C 0 0 0 0 0 0 0 0 0 10
2.7170 0.5320 -0.1220 H 0 0 0 0 0 0 0 0 0 11
2.5090 0.2980 -1.8740 H 0 0 0 0 0 0 0 0 0 12
2.1530 1.8790 -1.1380 H 0 0 0 0 0 0 0 0 0 13
0.8920 1.9610 0.6190 H 0 0 0 0 0 0 0 0 0 14
0.8730 0.5820 2.4360 H 0 0 0 0 0 0 0 0 0 15
-0.5820 -0.2910 1.8590 H 0 0 0 0 0 0 0 0 0 16
2.3520 -0.7300 1.0170 H 0 0 0 0 0 0 0 0 0 17
1.1420 -1.9630 1.5150 H 0 0 0 0 0 0 0 0 0 18
1.3230 -1.6860 -1.1970 H 0 0 0 0 0 0 0 0 0 19
-0.8020 -2.6100 -0.4940 H 0 0 0 0 0 0 0 0 0 20
-0.8430 -1.5380 0.9230 H 0 0 0 0 0 0 0 0 0 21
-1.2970 -0.3020 -1.7450 H 0 0 0 0 0 0 0 0 0 22
-2.5960 -1.3190 -1.0650 H 0 0 0 0 0 0 0 0 0 23
-3.0970 0.7120 -0.0900 H 0 0 0 0 0 0 0 0 0 24
-2.0640 -0.0150 1.1450 H 0 0 0 0 0 0 0 0 0 25
-1.5080 2.3240 0.8050 H 0 0 0 0 0 0 0 0 0 26
-1.1880 2.0080 -0.9220 H 0 0 0 0 0 0 0 0 0 27
2 1 1 0 0 0
2 6 1 0 0 0
2 3 1 0 0 0
1 11 1 0 0 0
1 13 1 0 0 0
1 12 1 0 0 0
3 4 1 0 0 0
3 10 1 0 0 0
3 14 1 0 0 0
4 5 1 0 0 0
4 15 1 0 0 0
4 16 1 0 0 0
5 17 1 0 0 0
5 18 1 0 0 0
5 6 1 0 0 0
6 19 1 0 0 0
6 7 1 0 0 0
7 8 1 0 0 0
7 20 1 0 0 0
7 21 1 0 0 0
8 22 1 0 0 0
8 23 1 0 0 0
8 9 1 0 0 0
9 10 1 0 0 0
9 25 1 0 0 0
9 24 1 0 0 0
10 26 1 0 0 0
10 27 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

'''Alkaloid''' means that is an amine that naturally occurs in a plant. In the case of hyoscine comes from plants in the nightshade family or jimson weed. Jimson weed comes from the Datura family which was investigated by Savary in 1989 to find out about the yields of scopolamine in tissue cultures of Datura.

==NMR Spectrum==

[[Image:Hyoscine_NMR.GIF]]

{| border="1"
|+ '''Chemical Shifts of Scopolamine'''
|-
! '''Carbon atom'''
| '''Scopolamine δ<sub>c</sub> from Me<sub>4</sub>Si'''
|-
! 1
| 171.3
|-
! 2
| 54.1
|-
! 3
| 63.5
|-
! 4
| 135.5
|-
! 5,9
| 128.5
|-
! 6,8
| 127.7
|-
! 7
| 127.5
|-
! 1',5'
| 57.3, 57.4
|-
! 2',4'
| 30.3, 30.4
|-
! 3'
| 66.4
|-
! 6', 7'
| 55.6, 56.0
|-
! 9'
| 41.6
|-
|}

It:Hycocine

2006-10-19T14:57:59Z

Raj105:

{|
| [[image:hyoscine.gif]] || <jmol>
<jmolApplet>
<size>300</size>
<color>black</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>hyoscine.pdb
title1
title2
ATOM 1 O 0 1.207 -1.433 0.214 0.00 0.00 O+0
ATOM 2 C 0 0.876 -0.299 0.465 0.00 0.00 C+0
ATOM 3 C 0 1.906 0.801 0.481 0.00 0.00 C+0
ATOM 4 H 0 1.934 1.258 1.470 0.00 0.00 H+0
ATOM 5 C 0 1.538 1.860 -0.560 0.00 0.00 C+0
ATOM 6 O 0 0.310 2.488 -0.187 0.00 0.00 O+0
ATOM 7 C 0 3.260 0.226 0.155 0.00 0.00 C+0
ATOM 8 C 0 4.294 0.333 1.066 0.00 0.00 C+0
ATOM 9 C 0 5.537 -0.195 0.767 0.00 0.00 C+0
ATOM 10 C 0 5.745 -0.830 -0.443 0.00 0.00 C+0
ATOM 11 C 0 4.710 -0.938 -1.354 0.00 0.00 C+0
ATOM 12 C 0 3.467 -0.414 -1.053 0.00 0.00 C+0
ATOM 13 O 0 -0.411 -0.017 0.723 0.00 0.00 O+0
ATOM 14 C 0 -1.401 -1.072 0.702 0.00 0.00 C+0
ATOM 15 C 0 -2.545 -0.794 1.661 0.00 0.00 C+0
ATOM 16 C 0 -3.763 -0.158 0.995 0.00 0.00 C+0
ATOM 17 C 0 -3.374 1.193 0.361 0.00 0.00 C+0
ATOM 18 O 0 -2.043 1.394 -0.100 0.00 0.00 O+0
ATOM 19 C 0 -2.916 0.830 -1.072 0.00 0.00 C+0
ATOM 20 C 0 -3.097 -0.697 -1.157 0.00 0.00 C+0
ATOM 21 C 0 -1.825 -1.419 -0.715 0.00 0.00 C+0
ATOM 22 N 0 -4.153 -1.012 -0.158 0.00 0.00 N+0
ATOM 23 C 0 -5.413 -0.472 -0.683 0.00 0.00 C+0
ATOM 24 H 0 2.328 2.610 -0.611 0.00 0.00 H+0
ATOM 25 H 0 1.423 1.387 -1.535 0.00 0.00 H+0
ATOM 26 H 0 0.114 3.146 -0.868 0.00 0.00 H+0
ATOM 27 H 0 4.132 0.829 2.012 0.00 0.00 H+0
ATOM 28 H 0 6.345 -0.111 1.479 0.00 0.00 H+0
ATOM 29 H 0 6.715 -1.242 -0.677 0.00 0.00 H+0
ATOM 30 H 0 4.873 -1.434 -2.299 0.00 0.00 H+0
ATOM 31 H 0 2.659 -0.498 -1.764 0.00 0.00 H+0
ATOM 32 H 0 -0.877 -1.978 1.099 0.00 0.00 H+0
ATOM 33 H 0 -2.851 -1.736 2.139 0.00 0.00 H+0
ATOM 34 H 0 -2.190 -0.131 2.463 0.00 0.00 H+0
ATOM 35 H 0 -4.596 -0.043 1.701 0.00 0.00 H+0
ATOM 36 H 0 -4.015 2.055 0.564 0.00 0.00 H+0
ATOM 37 H 0 -3.213 1.426 -1.941 0.00 0.00 H+0
ATOM 38 H 0 -3.406 -1.008 -2.165 0.00 0.00 H+0
ATOM 39 H 0 -1.011 -1.164 -1.408 0.00 0.00 H+0
ATOM 40 H 0 -1.985 -2.503 -0.790 0.00 0.00 H+0
ATOM 41 H 0 -5.637 -0.940 -1.642 0.00 0.00 H+0
ATOM 42 H 0 -6.219 -0.681 0.020 0.00 0.00 H+0
ATOM 43 H 0 -5.319 0.606 -0.818 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 48
CONECT 2 1 3 13 0 NONE 49
CONECT 3 2 4 5 7 NONE 50
CONECT 5 3 6 24 25 NONE 51
CONECT 6 5 26 0 0 NONE 52
CONECT 7 3 12 8 0 NONE 53
CONECT 8 7 9 27 0 NONE 54
CONECT 9 8 10 28 0 NONE 55
CONECT 10 9 11 29 0 NONE 56
CONECT 11 10 12 30 0 NONE 57
CONECT 12 11 7 31 0 NONE 58
CONECT 13 2 14 0 0 NONE 59
CONECT 14 13 21 15 32 NONE 60
CONECT 15 14 16 33 34 NONE 61
CONECT 16 15 22 17 35 NONE 62
CONECT 17 16 18 19 36 NONE 63
CONECT 18 17 19 0 0 NONE 64
CONECT 19 17 18 20 37 NONE 65
CONECT 20 19 21 22 38 NONE 66
CONECT 21 20 14 39 40 NONE 67
CONECT 22 20 16 23 0 NONE 68
CONECT 23 22 41 42 43 NONE 69
M END</inlineContents>
</jmolApplet>
</jmol>
|}

File:Hyoscine.gif

2006-10-19T14:33:28Z

Raj105: