ChemWiki - User contributions [en]

It:Artemisinin

2006-11-27T19:20:53Z

Vl105: added information about the preparation of artemisinin dimers

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Vlartemisinin.JPG|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 C 0 -0.961 3.875 0.476 0.00 0.00 C+0
ATOM 2 C 0 -0.183 2.558 0.526 0.00 0.00 C+0
ATOM 3 H 0 -0.205 2.169 1.543 0.00 0.00 H+0
ATOM 4 C 0 1.265 2.819 0.123 0.00 0.00 C+0
ATOM 5 C 0 2.037 1.498 0.225 0.00 0.00 C+0
ATOM 6 C 0 1.425 0.514 -0.763 0.00 0.00 C+0
ATOM 7 C 0 2.230 -0.786 -0.787 0.00 0.00 C+0
ATOM 8 H 0 1.916 -1.395 -1.634 0.00 0.00 H+0
ATOM 9 C 0 3.720 -0.464 -0.909 0.00 0.00 C+0
ATOM 10 H 0 1.464 0.959 -1.757 0.00 0.00 H+0
ATOM 11 C 0 -0.040 0.228 -0.438 0.00 0.00 C+0
ATOM 12 O 0 -0.562 -0.539 -1.538 0.00 0.00 O+0
ATOM 13 O 0 -1.235 -1.715 -0.997 0.00 0.00 O+0
ATOM 14 C 0 -0.848 1.548 -0.413 0.00 0.00 C+0
ATOM 15 H 0 -0.973 1.949 -1.419 0.00 0.00 H+0
ATOM 16 C 0 -2.208 1.203 0.220 0.00 0.00 C+0
ATOM 17 C 0 -2.845 0.045 -0.560 0.00 0.00 C+0
ATOM 18 C 0 -2.201 -1.246 -0.047 0.00 0.00 C+0
ATOM 19 C 0 -3.273 -2.305 0.219 0.00 0.00 C+0
ATOM 20 O 0 -1.511 -0.922 1.166 0.00 0.00 O+0
ATOM 21 C 0 -0.184 -0.527 0.865 0.00 0.00 C+0
ATOM 22 H 0 0.153 0.138 1.659 0.00 0.00 H+0
ATOM 23 O 0 0.682 -1.699 0.872 0.00 0.00 O+0
ATOM 24 C 0 1.971 -1.536 0.502 0.00 0.00 C+0
ATOM 25 O 0 2.879 -1.972 1.171 0.00 0.00 O+0
ATOM 26 H 0 -0.943 4.270 -0.539 0.00 0.00 H+0
ATOM 27 H 0 -1.994 3.698 0.779 0.00 0.00 H+0
ATOM 28 H 0 -0.502 4.594 1.155 0.00 0.00 H+0
ATOM 29 H 0 1.300 3.187 -0.903 0.00 0.00 H+0
ATOM 30 H 0 1.706 3.556 0.793 0.00 0.00 H+0
ATOM 31 H 0 3.085 1.664 -0.022 0.00 0.00 H+0
ATOM 32 H 0 1.955 1.102 1.238 0.00 0.00 H+0
ATOM 33 H 0 4.033 0.139 -0.057 0.00 0.00 H+0
ATOM 34 H 0 4.292 -1.392 -0.926 0.00 0.00 H+0
ATOM 35 H 0 3.898 0.089 -1.831 0.00 0.00 H+0
ATOM 36 H 0 -2.062 0.906 1.259 0.00 0.00 H+0
ATOM 37 H 0 -2.861 2.075 0.178 0.00 0.00 H+0
ATOM 38 H 0 -3.920 0.023 -0.381 0.00 0.00 H+0
ATOM 39 H 0 -2.646 0.161 -1.626 0.00 0.00 H+0
ATOM 40 H 0 -3.810 -2.518 -0.706 0.00 0.00 H+0
ATOM 41 H 0 -2.801 -3.217 0.583 0.00 0.00 H+0
ATOM 42 H 0 -3.972 -1.934 0.968 0.00 0.00 H+0
CONECT 1 2 26 27 28 NONE 47
CONECT 2 1 3 14 4 NONE 48
CONECT 4 2 5 29 30 NONE 49
CONECT 5 4 6 31 32 NONE 50
CONECT 6 5 7 10 11 NONE 51
CONECT 7 6 8 24 9 NONE 52
CONECT 9 7 33 34 35 NONE 53
CONECT 11 6 21 12 14 NONE 54
CONECT 12 11 13 0 0 NONE 55
CONECT 13 12 18 0 0 NONE 56
CONECT 14 11 15 2 16 NONE 57
CONECT 16 14 17 36 37 NONE 58
CONECT 17 16 18 38 39 NONE 59
CONECT 18 17 19 13 20 NONE 60
CONECT 19 18 40 41 42 NONE 61
CONECT 20 18 21 0 0 NONE 62
CONECT 21 20 22 11 23 NONE 63
CONECT 23 21 24 0 0 NONE 64
CONECT 24 23 7 25 0 NONE 65
CONECT 25 24 0 0 0 NONE 66
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Molecular weight]]
| colspan="2"| 282.332 g/mol
|-
| [[Molecular Formula]]
|colspan="2"| C15H22O5
|-
| [[SMILES]]
| colspan="2"|

C[C@@H]1CC[C@]([C@H]3C)([H])[C@]2(OO4)[C@]([H])1CC[C@@]
(C)4O[C@]([H])2OC3=O

|-
| [[CA index name]]
| colspan="2"| 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one,
octahydro-3,6,9-trimethyl-,
(3R,5aS,6R,8aS,9R,12S,12aR)- (9CI)
|-
| [[Other names]]
| colspan="2"|
(+)-Arteannuin;
(+)-Artemisinin;
(+)-Qinghaosu;
Arteannuin;
Artemef;
Artemisine;
Artemisinin;
Artemisinine;
Huanghuahaosu;
NSC 369397;
QHS;
Qing Hau Sau;
Qing Hau Su;
Qinghaosu;
Qinghosu
|-
| [[Boiling point]]
| colspan="2"|389.9±42.0 °C
|-
| [[Density]]
| colspan="2"|1.24±0.1 g/cm3
|-
| [[Enthalpy of vaporization]]
| colspan="2"|63.93±3.0 kJ/mol
|-
| [[Flash point]]
| colspan="2"|172.0±27.9 °C
|}

Artemisinin is a drug that is used to treat malaria. This compound is obtained from the leaves of the shrub ''‘Artemesia annua’'', which is cultivated in China [http://www.medterms.com/script/main/art.asp?articlekey=24010]. Artemisinin affects the malaria parasite, which is responsible for the malaria disease in humans. The drug has no significant side effects and reduces the malarial fever.

The information in the box on the right (containing the 2d structure, 3d structure, molecular weight etc...) was obtained from SciFinder Scholar [ref 2].

==Effectiveness of the drug==

Artemisia has a great potential for being an effective drug to treat malaria, which is a disease that affects more than 300 million people a year (ref 3). Malaria kills about one million people a year (mainly young children), in sub-Saharan Africa and south Asia. Clinical trials in some countries (such as India, Indonesia, and Vietnam) have that over 90% of patients have recovered from malaria, when treated by using Artemisinin-based Combination Therapies (ACTs).

==History==

The Artemisia plant has been used in Chinese medicine for over a thousand years, but only in the 1960’s when military scientists in China started to analyse the large variety of Chinese traditional medicines, to find a substance that will protect the Chinese military from the malaria disease. The researchers were able to extract a chemical known as Artemisinin, which had the desired anti-malarial properties. The step from the 1960’s was to modify Artemisinin to become more potent against malaria, because the malaria parasite can evolve (by natural selection) to survive in the presence of Artemisinin. This has lead to scientists modifying the groups in Artemisinin, to produce a more potent drug.

==Proposed mechanism of attacking the malarial parasite==

The mechanism of how Artemisinin kills the malaria parasite is not well known. Theories have been proposed (ref 4-{{doi-inline|10.1021/ar000080b|proposed mechanisms of how Artemisinin kills the malaria parasite}}), but it had been difficult to develop further as not enough evidence have been obtained.

One theory states that Artemisinin does not affect the malaria parasite as a whole intact molecule, but via a species of a transition state (having a fleeting existence) that is formed after the cleaving of the peroxy bond (O-O bond). Then this species attacks the malaria parasite.

Another theory states that the anti-malarial properties of Artemisinin are due to the direct O2 transfer from a hydroperoxide ROOH group (from the ring-opening in Artemisinin). Then the reactive oxygen centered radicals formed from ROOH, attacks the haem group in the malaria parasite’s blood (red blood cells), which should kill the parasites.

More research is required to figure out the exact mechanism of how Artemisinin affects the malaria parasite.

==Synthesis of Artemisinin derived dimers==

Artemisinin derived dimers can be synthesised by a self-cross metathesis reaction (ref 5- {{doi-inline|10.1021/ol052056+|article on metathesis reaction}}). The dimers are prepared with ruthenium catalysts, and this catalyst does not cleave open the O-O peroxy bond.

[[Image:vlartemisinindimer.jpg]]

Therefore the peroxide bond can still form oxygen centered radicals (to kill malaria parasites) when in the dimer form. The peroxide bond is also toxic to tumor cells in cancer diseases. The peroxide bond is more effective against tumor cells, when in the dimer form of Artemisinin.

The self-cross metathesis reaction for the preparation of Artemisinin derived dimers had been founded upon from the work of the olefin (alkene) metathesis reaction of the past several years. Ruthenium based catalysts are used because of their stability, reactivity and functional group tolerance.

==References==

1) http://www.medterms.com/script/main/art.asp?articlekey=24010

2) SciFinder Scholar

3) Economist 11/20/2004, Vol. 373 Issue 8402, p81

4) {{doi-inline|10.1021/ar000080b|proposed mechanisms of how Artemisinin kills the malaria parasite}}

5) {{doi-inline|10.1021/ol052056+|article on metathesis reaction}}

File:Vlartemisinindimer.jpg

2006-11-27T19:17:32Z

Vl105: reaction scheme for artemisinin dimer preparation

reaction scheme for artemisinin dimer preparation

File:Vlartemisinindimer.JPG

2006-11-27T19:13:45Z

Vl105: reaction scheme for artemisinin dimer preparation

reaction scheme for artemisinin dimer preparation

It:Artemisinin

2006-11-27T19:13:01Z

Vl105:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Vlartemisinin.JPG|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 C 0 -0.961 3.875 0.476 0.00 0.00 C+0
ATOM 2 C 0 -0.183 2.558 0.526 0.00 0.00 C+0
ATOM 3 H 0 -0.205 2.169 1.543 0.00 0.00 H+0
ATOM 4 C 0 1.265 2.819 0.123 0.00 0.00 C+0
ATOM 5 C 0 2.037 1.498 0.225 0.00 0.00 C+0
ATOM 6 C 0 1.425 0.514 -0.763 0.00 0.00 C+0
ATOM 7 C 0 2.230 -0.786 -0.787 0.00 0.00 C+0
ATOM 8 H 0 1.916 -1.395 -1.634 0.00 0.00 H+0
ATOM 9 C 0 3.720 -0.464 -0.909 0.00 0.00 C+0
ATOM 10 H 0 1.464 0.959 -1.757 0.00 0.00 H+0
ATOM 11 C 0 -0.040 0.228 -0.438 0.00 0.00 C+0
ATOM 12 O 0 -0.562 -0.539 -1.538 0.00 0.00 O+0
ATOM 13 O 0 -1.235 -1.715 -0.997 0.00 0.00 O+0
ATOM 14 C 0 -0.848 1.548 -0.413 0.00 0.00 C+0
ATOM 15 H 0 -0.973 1.949 -1.419 0.00 0.00 H+0
ATOM 16 C 0 -2.208 1.203 0.220 0.00 0.00 C+0
ATOM 17 C 0 -2.845 0.045 -0.560 0.00 0.00 C+0
ATOM 18 C 0 -2.201 -1.246 -0.047 0.00 0.00 C+0
ATOM 19 C 0 -3.273 -2.305 0.219 0.00 0.00 C+0
ATOM 20 O 0 -1.511 -0.922 1.166 0.00 0.00 O+0
ATOM 21 C 0 -0.184 -0.527 0.865 0.00 0.00 C+0
ATOM 22 H 0 0.153 0.138 1.659 0.00 0.00 H+0
ATOM 23 O 0 0.682 -1.699 0.872 0.00 0.00 O+0
ATOM 24 C 0 1.971 -1.536 0.502 0.00 0.00 C+0
ATOM 25 O 0 2.879 -1.972 1.171 0.00 0.00 O+0
ATOM 26 H 0 -0.943 4.270 -0.539 0.00 0.00 H+0
ATOM 27 H 0 -1.994 3.698 0.779 0.00 0.00 H+0
ATOM 28 H 0 -0.502 4.594 1.155 0.00 0.00 H+0
ATOM 29 H 0 1.300 3.187 -0.903 0.00 0.00 H+0
ATOM 30 H 0 1.706 3.556 0.793 0.00 0.00 H+0
ATOM 31 H 0 3.085 1.664 -0.022 0.00 0.00 H+0
ATOM 32 H 0 1.955 1.102 1.238 0.00 0.00 H+0
ATOM 33 H 0 4.033 0.139 -0.057 0.00 0.00 H+0
ATOM 34 H 0 4.292 -1.392 -0.926 0.00 0.00 H+0
ATOM 35 H 0 3.898 0.089 -1.831 0.00 0.00 H+0
ATOM 36 H 0 -2.062 0.906 1.259 0.00 0.00 H+0
ATOM 37 H 0 -2.861 2.075 0.178 0.00 0.00 H+0
ATOM 38 H 0 -3.920 0.023 -0.381 0.00 0.00 H+0
ATOM 39 H 0 -2.646 0.161 -1.626 0.00 0.00 H+0
ATOM 40 H 0 -3.810 -2.518 -0.706 0.00 0.00 H+0
ATOM 41 H 0 -2.801 -3.217 0.583 0.00 0.00 H+0
ATOM 42 H 0 -3.972 -1.934 0.968 0.00 0.00 H+0
CONECT 1 2 26 27 28 NONE 47
CONECT 2 1 3 14 4 NONE 48
CONECT 4 2 5 29 30 NONE 49
CONECT 5 4 6 31 32 NONE 50
CONECT 6 5 7 10 11 NONE 51
CONECT 7 6 8 24 9 NONE 52
CONECT 9 7 33 34 35 NONE 53
CONECT 11 6 21 12 14 NONE 54
CONECT 12 11 13 0 0 NONE 55
CONECT 13 12 18 0 0 NONE 56
CONECT 14 11 15 2 16 NONE 57
CONECT 16 14 17 36 37 NONE 58
CONECT 17 16 18 38 39 NONE 59
CONECT 18 17 19 13 20 NONE 60
CONECT 19 18 40 41 42 NONE 61
CONECT 20 18 21 0 0 NONE 62
CONECT 21 20 22 11 23 NONE 63
CONECT 23 21 24 0 0 NONE 64
CONECT 24 23 7 25 0 NONE 65
CONECT 25 24 0 0 0 NONE 66
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Molecular weight]]
| colspan="2"| 282.332 g/mol
|-
| [[Molecular Formula]]
|colspan="2"| C15H22O5
|-
| [[SMILES]]
| colspan="2"|

C[C@@H]1CC[C@]([C@H]3C)([H])[C@]2(OO4)[C@]([H])1CC[C@@]
(C)4O[C@]([H])2OC3=O

|-
| [[CA index name]]
| colspan="2"| 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one,
octahydro-3,6,9-trimethyl-,
(3R,5aS,6R,8aS,9R,12S,12aR)- (9CI)
|-
| [[Other names]]
| colspan="2"|
(+)-Arteannuin;
(+)-Artemisinin;
(+)-Qinghaosu;
Arteannuin;
Artemef;
Artemisine;
Artemisinin;
Artemisinine;
Huanghuahaosu;
NSC 369397;
QHS;
Qing Hau Sau;
Qing Hau Su;
Qinghaosu;
Qinghosu
|-
| [[Boiling point]]
| colspan="2"|389.9±42.0 °C
|-
| [[Density]]
| colspan="2"|1.24±0.1 g/cm3
|-
| [[Enthalpy of vaporization]]
| colspan="2"|63.93±3.0 kJ/mol
|-
| [[Flash point]]
| colspan="2"|172.0±27.9 °C
|}

Artemisinin is a drug that is used to treat malaria. This compound is obtained from the leaves of the shrub ''‘Artemesia annua’'', which is cultivated in China [http://www.medterms.com/script/main/art.asp?articlekey=24010]. Artemisinin affects the malaria parasite, which is responsible for the malaria disease in humans. The drug has no significant side effects and reduces the malarial fever.

The information in the box on the right (containing the 2d structure, 3d structure, molecular weight etc...) was obtained from SciFinder Scholar [ref 2].

==Effectiveness of the drug==

Artemisia has a great potential for being an effective drug to treat malaria, which is a disease that affects more than 300 million people a year (ref 3). Malaria kills about one million people a year (mainly young children), in sub-Saharan Africa and south Asia. Clinical trials in some countries (such as India, Indonesia, and Vietnam) have that over 90% of patients have recovered from malaria, when treated by using Artemisinin-based Combination Therapies (ACTs).

==History==

The Artemisia plant has been used in Chinese medicine for over a thousand years, but only in the 1960’s when military scientists in China started to analyse the large variety of Chinese traditional medicines, to find a substance that will protect the Chinese military from the malaria disease. The researchers were able to extract a chemical known as Artemisinin, which had the desired anti-malarial properties. The step from the 1960’s was to modify Artemisinin to become more potent against malaria, because the malaria parasite can evolve (by natural selection) to survive in the presence of Artemisinin. This has lead to scientists modifying the groups in Artemisinin, to produce a more potent drug.

==Proposed mechanism of attacking the malarial parasite==

The mechanism of how Artemisinin kills the malaria parasite is not well known. Theories have been proposed (ref 4-{{doi-inline|10.1021/ar000080b|proposed mechanisms of how Artemisinin kills the malaria parasite}}), but it had been difficult to develop further as not enough evidence have been obtained.

One theory states that Artemisinin does not affect the malaria parasite as a whole intact molecule, but via a species of a transition state (having a fleeting existence) that is formed after the cleaving of the peroxy bond (O-O bond). Then this species attacks the malaria parasite.

Another theory states that the anti-malarial properties of Artemisinin are due to the direct O2 transfer from a hydroperoxide ROOH group (from the ring-opening in Artemisinin). Then the reactive oxygen centered radicals formed from ROOH, attacks the haem group in the malaria parasite’s blood (red blood cells), which should kill the parasites.

More research is required to figure out the exact mechanism of how Artemisinin affects the malaria parasite.

==Synthesis of Artemisinin derived dimers==

==References==

1) http://www.medterms.com/script/main/art.asp?articlekey=24010

2) SciFinder Scholar

3) Economist 11/20/2004, Vol. 373 Issue 8402, p81

4) {{doi-inline|10.1021/ar000080b|proposed mechanisms of how Artemisinin kills the malaria parasite}}

It:Artemisinin

2006-11-27T16:51:49Z

Vl105: added information of how the drug affects the malarial parasite

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Vlartemisinin.JPG|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 C 0 -0.961 3.875 0.476 0.00 0.00 C+0
ATOM 2 C 0 -0.183 2.558 0.526 0.00 0.00 C+0
ATOM 3 H 0 -0.205 2.169 1.543 0.00 0.00 H+0
ATOM 4 C 0 1.265 2.819 0.123 0.00 0.00 C+0
ATOM 5 C 0 2.037 1.498 0.225 0.00 0.00 C+0
ATOM 6 C 0 1.425 0.514 -0.763 0.00 0.00 C+0
ATOM 7 C 0 2.230 -0.786 -0.787 0.00 0.00 C+0
ATOM 8 H 0 1.916 -1.395 -1.634 0.00 0.00 H+0
ATOM 9 C 0 3.720 -0.464 -0.909 0.00 0.00 C+0
ATOM 10 H 0 1.464 0.959 -1.757 0.00 0.00 H+0
ATOM 11 C 0 -0.040 0.228 -0.438 0.00 0.00 C+0
ATOM 12 O 0 -0.562 -0.539 -1.538 0.00 0.00 O+0
ATOM 13 O 0 -1.235 -1.715 -0.997 0.00 0.00 O+0
ATOM 14 C 0 -0.848 1.548 -0.413 0.00 0.00 C+0
ATOM 15 H 0 -0.973 1.949 -1.419 0.00 0.00 H+0
ATOM 16 C 0 -2.208 1.203 0.220 0.00 0.00 C+0
ATOM 17 C 0 -2.845 0.045 -0.560 0.00 0.00 C+0
ATOM 18 C 0 -2.201 -1.246 -0.047 0.00 0.00 C+0
ATOM 19 C 0 -3.273 -2.305 0.219 0.00 0.00 C+0
ATOM 20 O 0 -1.511 -0.922 1.166 0.00 0.00 O+0
ATOM 21 C 0 -0.184 -0.527 0.865 0.00 0.00 C+0
ATOM 22 H 0 0.153 0.138 1.659 0.00 0.00 H+0
ATOM 23 O 0 0.682 -1.699 0.872 0.00 0.00 O+0
ATOM 24 C 0 1.971 -1.536 0.502 0.00 0.00 C+0
ATOM 25 O 0 2.879 -1.972 1.171 0.00 0.00 O+0
ATOM 26 H 0 -0.943 4.270 -0.539 0.00 0.00 H+0
ATOM 27 H 0 -1.994 3.698 0.779 0.00 0.00 H+0
ATOM 28 H 0 -0.502 4.594 1.155 0.00 0.00 H+0
ATOM 29 H 0 1.300 3.187 -0.903 0.00 0.00 H+0
ATOM 30 H 0 1.706 3.556 0.793 0.00 0.00 H+0
ATOM 31 H 0 3.085 1.664 -0.022 0.00 0.00 H+0
ATOM 32 H 0 1.955 1.102 1.238 0.00 0.00 H+0
ATOM 33 H 0 4.033 0.139 -0.057 0.00 0.00 H+0
ATOM 34 H 0 4.292 -1.392 -0.926 0.00 0.00 H+0
ATOM 35 H 0 3.898 0.089 -1.831 0.00 0.00 H+0
ATOM 36 H 0 -2.062 0.906 1.259 0.00 0.00 H+0
ATOM 37 H 0 -2.861 2.075 0.178 0.00 0.00 H+0
ATOM 38 H 0 -3.920 0.023 -0.381 0.00 0.00 H+0
ATOM 39 H 0 -2.646 0.161 -1.626 0.00 0.00 H+0
ATOM 40 H 0 -3.810 -2.518 -0.706 0.00 0.00 H+0
ATOM 41 H 0 -2.801 -3.217 0.583 0.00 0.00 H+0
ATOM 42 H 0 -3.972 -1.934 0.968 0.00 0.00 H+0
CONECT 1 2 26 27 28 NONE 47
CONECT 2 1 3 14 4 NONE 48
CONECT 4 2 5 29 30 NONE 49
CONECT 5 4 6 31 32 NONE 50
CONECT 6 5 7 10 11 NONE 51
CONECT 7 6 8 24 9 NONE 52
CONECT 9 7 33 34 35 NONE 53
CONECT 11 6 21 12 14 NONE 54
CONECT 12 11 13 0 0 NONE 55
CONECT 13 12 18 0 0 NONE 56
CONECT 14 11 15 2 16 NONE 57
CONECT 16 14 17 36 37 NONE 58
CONECT 17 16 18 38 39 NONE 59
CONECT 18 17 19 13 20 NONE 60
CONECT 19 18 40 41 42 NONE 61
CONECT 20 18 21 0 0 NONE 62
CONECT 21 20 22 11 23 NONE 63
CONECT 23 21 24 0 0 NONE 64
CONECT 24 23 7 25 0 NONE 65
CONECT 25 24 0 0 0 NONE 66
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Molecular weight]]
| colspan="2"| 282.332 g/mol
|-
| [[Molecular Formula]]
|colspan="2"| C15H22O5
|-
| [[SMILES]]
| colspan="2"|

C[C@@H]1CC[C@]([C@H]3C)([H])[C@]2(OO4)[C@]([H])1CC[C@@]
(C)4O[C@]([H])2OC3=O

|-
| [[CA index name]]
| colspan="2"| 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one,
octahydro-3,6,9-trimethyl-,
(3R,5aS,6R,8aS,9R,12S,12aR)- (9CI)
|-
| [[Other names]]
| colspan="2"|
(+)-Arteannuin;
(+)-Artemisinin;
(+)-Qinghaosu;
Arteannuin;
Artemef;
Artemisine;
Artemisinin;
Artemisinine;
Huanghuahaosu;
NSC 369397;
QHS;
Qing Hau Sau;
Qing Hau Su;
Qinghaosu;
Qinghosu
|-
| [[Boiling point]]
| colspan="2"|389.9±42.0 °C
|-
| [[Density]]
| colspan="2"|1.24±0.1 g/cm3
|-
| [[Enthalpy of vaporization]]
| colspan="2"|63.93±3.0 kJ/mol
|-
| [[Flash point]]
| colspan="2"|172.0±27.9 °C
|}

Artemisinin is a drug that is used to treat malaria. This compound is obtained from the leaves of the shrub ‘Artemesia annua’, which is cultivated in China (ref 1). Artemisinin affects the malaria parasite, which is responsible for the malaria disease in humans. The drug has no significant side effects and reduces the malarial fever.

The information in the box on the right (containing the 2d structure, 3d structure, molecular weight etc...) was obtained from SciFinder Scholar (ref 2).

==Effectiveness of the drug==

Artemisia has a great potential for being an effective drug to treat malaria, which is a disease that affects more than 300 million people a year (ref 3). Malaria kills about one million people a year (mainly young children), in sub-Saharan Africa and south Asia. Clinical trials in some countries (such as India, Indonesia, and Vietnam) have that over 90% of patients have recovered from malaria, when treated by using Artemisinin-based Combination Therapies (ACTs).

==History==

The Artemisia plant has been used in Chinese medicine for over a thousand years, but only in the 1960’s when military scientists in China started to analyse the large variety of Chinese traditional medicines, to find a substance that will protect the Chinese military from the malaria disease. The researchers were able to extract a chemical known as Artemisinin, which had the desired anti-malarial properties. The step from the 1960’s was to modify Artemisinin to become more potent against malaria, because the malaria parasite can evolve (by natural selection) to survive in the presence of Artemisinin. This has lead to scientists modifying the groups in Artemisinin, to produce a more potent drug.

==Proposed mechanism of attacking the malarial parasite==

The mechanism of how Artemisinin kills the malaria parasite is not well known. Theories have been proposed (ref 4-{{doi-inline|10.1021/ar000080b|proposed mechanisms of how Artemisinin kills the malaria parasite}}), but it had been difficult to develop further as not enough evidence have been obtained.

One theory states that Artemisinin does not affect the malaria parasite as a whole intact molecule, but via a species of a transition state (having a fleeting existence) that is formed after the cleaving of the peroxy bond (O-O bond). Then this species attacks the malaria parasite.

Another theory states that the anti-malarial properties of Artemisinin are due to the direct O2 transfer from a hydroperoxide ROOH group (from the ring-opening in Artemisinin). Then the reactive oxygen centered radicals formed from ROOH, attacks the haem group in the malaria parasite’s blood (red blood cells), which should kill the parasites.

More research is required to figure out the exact mechanism of how Artemisinin affects the malaria parasite.

==References==

1) http://www.medterms.com/script/main/art.asp?articlekey=24010

2) SciFinder Scholar

3) Economist 11/20/2004, Vol. 373 Issue 8402, p81

4) {{doi-inline|10.1021/ar000080b|proposed mechanisms of how Artemisinin kills the malaria parasite}}

It:Artemisinin

2006-11-27T16:16:42Z

Vl105:

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Vlartemisinin.JPG|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 C 0 -0.961 3.875 0.476 0.00 0.00 C+0
ATOM 2 C 0 -0.183 2.558 0.526 0.00 0.00 C+0
ATOM 3 H 0 -0.205 2.169 1.543 0.00 0.00 H+0
ATOM 4 C 0 1.265 2.819 0.123 0.00 0.00 C+0
ATOM 5 C 0 2.037 1.498 0.225 0.00 0.00 C+0
ATOM 6 C 0 1.425 0.514 -0.763 0.00 0.00 C+0
ATOM 7 C 0 2.230 -0.786 -0.787 0.00 0.00 C+0
ATOM 8 H 0 1.916 -1.395 -1.634 0.00 0.00 H+0
ATOM 9 C 0 3.720 -0.464 -0.909 0.00 0.00 C+0
ATOM 10 H 0 1.464 0.959 -1.757 0.00 0.00 H+0
ATOM 11 C 0 -0.040 0.228 -0.438 0.00 0.00 C+0
ATOM 12 O 0 -0.562 -0.539 -1.538 0.00 0.00 O+0
ATOM 13 O 0 -1.235 -1.715 -0.997 0.00 0.00 O+0
ATOM 14 C 0 -0.848 1.548 -0.413 0.00 0.00 C+0
ATOM 15 H 0 -0.973 1.949 -1.419 0.00 0.00 H+0
ATOM 16 C 0 -2.208 1.203 0.220 0.00 0.00 C+0
ATOM 17 C 0 -2.845 0.045 -0.560 0.00 0.00 C+0
ATOM 18 C 0 -2.201 -1.246 -0.047 0.00 0.00 C+0
ATOM 19 C 0 -3.273 -2.305 0.219 0.00 0.00 C+0
ATOM 20 O 0 -1.511 -0.922 1.166 0.00 0.00 O+0
ATOM 21 C 0 -0.184 -0.527 0.865 0.00 0.00 C+0
ATOM 22 H 0 0.153 0.138 1.659 0.00 0.00 H+0
ATOM 23 O 0 0.682 -1.699 0.872 0.00 0.00 O+0
ATOM 24 C 0 1.971 -1.536 0.502 0.00 0.00 C+0
ATOM 25 O 0 2.879 -1.972 1.171 0.00 0.00 O+0
ATOM 26 H 0 -0.943 4.270 -0.539 0.00 0.00 H+0
ATOM 27 H 0 -1.994 3.698 0.779 0.00 0.00 H+0
ATOM 28 H 0 -0.502 4.594 1.155 0.00 0.00 H+0
ATOM 29 H 0 1.300 3.187 -0.903 0.00 0.00 H+0
ATOM 30 H 0 1.706 3.556 0.793 0.00 0.00 H+0
ATOM 31 H 0 3.085 1.664 -0.022 0.00 0.00 H+0
ATOM 32 H 0 1.955 1.102 1.238 0.00 0.00 H+0
ATOM 33 H 0 4.033 0.139 -0.057 0.00 0.00 H+0
ATOM 34 H 0 4.292 -1.392 -0.926 0.00 0.00 H+0
ATOM 35 H 0 3.898 0.089 -1.831 0.00 0.00 H+0
ATOM 36 H 0 -2.062 0.906 1.259 0.00 0.00 H+0
ATOM 37 H 0 -2.861 2.075 0.178 0.00 0.00 H+0
ATOM 38 H 0 -3.920 0.023 -0.381 0.00 0.00 H+0
ATOM 39 H 0 -2.646 0.161 -1.626 0.00 0.00 H+0
ATOM 40 H 0 -3.810 -2.518 -0.706 0.00 0.00 H+0
ATOM 41 H 0 -2.801 -3.217 0.583 0.00 0.00 H+0
ATOM 42 H 0 -3.972 -1.934 0.968 0.00 0.00 H+0
CONECT 1 2 26 27 28 NONE 47
CONECT 2 1 3 14 4 NONE 48
CONECT 4 2 5 29 30 NONE 49
CONECT 5 4 6 31 32 NONE 50
CONECT 6 5 7 10 11 NONE 51
CONECT 7 6 8 24 9 NONE 52
CONECT 9 7 33 34 35 NONE 53
CONECT 11 6 21 12 14 NONE 54
CONECT 12 11 13 0 0 NONE 55
CONECT 13 12 18 0 0 NONE 56
CONECT 14 11 15 2 16 NONE 57
CONECT 16 14 17 36 37 NONE 58
CONECT 17 16 18 38 39 NONE 59
CONECT 18 17 19 13 20 NONE 60
CONECT 19 18 40 41 42 NONE 61
CONECT 20 18 21 0 0 NONE 62
CONECT 21 20 22 11 23 NONE 63
CONECT 23 21 24 0 0 NONE 64
CONECT 24 23 7 25 0 NONE 65
CONECT 25 24 0 0 0 NONE 66
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Molecular weight]]
| colspan="2"| 282.332 g/mol
|-
| [[Molecular Formula]]
|colspan="2"| C15H22O5
|-
| [[SMILES]]
| colspan="2"|

C[C@@H]1CC[C@]([C@H]3C)([H])[C@]2(OO4)[C@]([H])1CC[C@@]
(C)4O[C@]([H])2OC3=O

|-
| [[CA index name]]
| colspan="2"| 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one,
octahydro-3,6,9-trimethyl-,
(3R,5aS,6R,8aS,9R,12S,12aR)- (9CI)
|-
| [[Other names]]
| colspan="2"|
(+)-Arteannuin;
(+)-Artemisinin;
(+)-Qinghaosu;
Arteannuin;
Artemef;
Artemisine;
Artemisinin;
Artemisinine;
Huanghuahaosu;
NSC 369397;
QHS;
Qing Hau Sau;
Qing Hau Su;
Qinghaosu;
Qinghosu
|-
| [[Boiling point]]
| colspan="2"|389.9±42.0 °C
|-
| [[Density]]
| colspan="2"|1.24±0.1 g/cm3
|-
| [[Enthalpy of vaporization]]
| colspan="2"|63.93±3.0 kJ/mol
|-
| [[Flash point]]
| colspan="2"|172.0±27.9 °C
|}

Artemisinin is a drug that is used to treat malaria. This compound is obtained from the leaves of the shrub ‘Artemesia annua’, which is cultivated in China (ref 1). Artemisinin affects the malarial parasite, which is responsible for the malaria disease in humans. The drug has no significant side effects and reduces the malarial fever.

The information in the box on the right (containing the 2d structure, 3d structure, molecular weight etc...) was obtained from SciFinder Scholar (ref 2).

==Effectiveness of the drug==

Artemisia has a great potential for being an effective drug to treat malaria, which is a disease that affects more than 300 million people a year (ref 3). Malaria kills about one million people a year (mainly young children), in sub-Saharan Africa and south Asia. Clinical trials in some countries (such as India, Indonesia, and Vietnam) have that over 90% of patients have recovered from malaria, when treated by using Artemisinin-based Combination Therapies (ACTs).

==History==

The Artemisia plant has been used in Chinese medicine for over a thousand years, but only in the 1960’s when military scientists in China started to analyse the large variety of Chinese traditional medicines, to find a substance that will protect the Chinese military from the malaria disease. The researchers were able to extract a chemical known as Artemisinin, which had the desired anti-malarial properties. The step from the 1960’s was to modify Artemisinin to become more potent against malaria, because the malaria parasite can evolve (by natural selection) to survive in the presence of Artemisinin. This has lead to scientists modifying the groups in Artemisinin, to produce a more potent drug.

==References==

1) http://www.medterms.com/script/main/art.asp?articlekey=24010

2) SciFinder Scholar

3) Economist 11/20/2004, Vol. 373 Issue 8402, p81

It:Artemisinin

2006-11-27T15:55:23Z

Vl105: added some information

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Vlartemisinin.JPG|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 C 0 -0.961 3.875 0.476 0.00 0.00 C+0
ATOM 2 C 0 -0.183 2.558 0.526 0.00 0.00 C+0
ATOM 3 H 0 -0.205 2.169 1.543 0.00 0.00 H+0
ATOM 4 C 0 1.265 2.819 0.123 0.00 0.00 C+0
ATOM 5 C 0 2.037 1.498 0.225 0.00 0.00 C+0
ATOM 6 C 0 1.425 0.514 -0.763 0.00 0.00 C+0
ATOM 7 C 0 2.230 -0.786 -0.787 0.00 0.00 C+0
ATOM 8 H 0 1.916 -1.395 -1.634 0.00 0.00 H+0
ATOM 9 C 0 3.720 -0.464 -0.909 0.00 0.00 C+0
ATOM 10 H 0 1.464 0.959 -1.757 0.00 0.00 H+0
ATOM 11 C 0 -0.040 0.228 -0.438 0.00 0.00 C+0
ATOM 12 O 0 -0.562 -0.539 -1.538 0.00 0.00 O+0
ATOM 13 O 0 -1.235 -1.715 -0.997 0.00 0.00 O+0
ATOM 14 C 0 -0.848 1.548 -0.413 0.00 0.00 C+0
ATOM 15 H 0 -0.973 1.949 -1.419 0.00 0.00 H+0
ATOM 16 C 0 -2.208 1.203 0.220 0.00 0.00 C+0
ATOM 17 C 0 -2.845 0.045 -0.560 0.00 0.00 C+0
ATOM 18 C 0 -2.201 -1.246 -0.047 0.00 0.00 C+0
ATOM 19 C 0 -3.273 -2.305 0.219 0.00 0.00 C+0
ATOM 20 O 0 -1.511 -0.922 1.166 0.00 0.00 O+0
ATOM 21 C 0 -0.184 -0.527 0.865 0.00 0.00 C+0
ATOM 22 H 0 0.153 0.138 1.659 0.00 0.00 H+0
ATOM 23 O 0 0.682 -1.699 0.872 0.00 0.00 O+0
ATOM 24 C 0 1.971 -1.536 0.502 0.00 0.00 C+0
ATOM 25 O 0 2.879 -1.972 1.171 0.00 0.00 O+0
ATOM 26 H 0 -0.943 4.270 -0.539 0.00 0.00 H+0
ATOM 27 H 0 -1.994 3.698 0.779 0.00 0.00 H+0
ATOM 28 H 0 -0.502 4.594 1.155 0.00 0.00 H+0
ATOM 29 H 0 1.300 3.187 -0.903 0.00 0.00 H+0
ATOM 30 H 0 1.706 3.556 0.793 0.00 0.00 H+0
ATOM 31 H 0 3.085 1.664 -0.022 0.00 0.00 H+0
ATOM 32 H 0 1.955 1.102 1.238 0.00 0.00 H+0
ATOM 33 H 0 4.033 0.139 -0.057 0.00 0.00 H+0
ATOM 34 H 0 4.292 -1.392 -0.926 0.00 0.00 H+0
ATOM 35 H 0 3.898 0.089 -1.831 0.00 0.00 H+0
ATOM 36 H 0 -2.062 0.906 1.259 0.00 0.00 H+0
ATOM 37 H 0 -2.861 2.075 0.178 0.00 0.00 H+0
ATOM 38 H 0 -3.920 0.023 -0.381 0.00 0.00 H+0
ATOM 39 H 0 -2.646 0.161 -1.626 0.00 0.00 H+0
ATOM 40 H 0 -3.810 -2.518 -0.706 0.00 0.00 H+0
ATOM 41 H 0 -2.801 -3.217 0.583 0.00 0.00 H+0
ATOM 42 H 0 -3.972 -1.934 0.968 0.00 0.00 H+0
CONECT 1 2 26 27 28 NONE 47
CONECT 2 1 3 14 4 NONE 48
CONECT 4 2 5 29 30 NONE 49
CONECT 5 4 6 31 32 NONE 50
CONECT 6 5 7 10 11 NONE 51
CONECT 7 6 8 24 9 NONE 52
CONECT 9 7 33 34 35 NONE 53
CONECT 11 6 21 12 14 NONE 54
CONECT 12 11 13 0 0 NONE 55
CONECT 13 12 18 0 0 NONE 56
CONECT 14 11 15 2 16 NONE 57
CONECT 16 14 17 36 37 NONE 58
CONECT 17 16 18 38 39 NONE 59
CONECT 18 17 19 13 20 NONE 60
CONECT 19 18 40 41 42 NONE 61
CONECT 20 18 21 0 0 NONE 62
CONECT 21 20 22 11 23 NONE 63
CONECT 23 21 24 0 0 NONE 64
CONECT 24 23 7 25 0 NONE 65
CONECT 25 24 0 0 0 NONE 66
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Molecular weight]]
| colspan="2"| 282.332 g/mol
|-
| [[Molecular Formula]]
|colspan="2"| C15H22O5
|-
| [[SMILES]]
| colspan="2"|

C[C@@H]1CC[C@]([C@H]3C)([H])[C@]2(OO4)[C@]([H])1CC[C@@]
(C)4O[C@]([H])2OC3=O

|-
| [[CA index name]]
| colspan="2"| 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one,
octahydro-3,6,9-trimethyl-,
(3R,5aS,6R,8aS,9R,12S,12aR)- (9CI)
|-
| [[Other names]]
| colspan="2"|
(+)-Arteannuin;
(+)-Artemisinin;
(+)-Qinghaosu;
Arteannuin;
Artemef;
Artemisine;
Artemisinin;
Artemisinine;
Huanghuahaosu;
NSC 369397;
QHS;
Qing Hau Sau;
Qing Hau Su;
Qinghaosu;
Qinghosu
|-
| [[Boiling point]]
| colspan="2"|389.9±42.0 °C
|-
| [[Density]]
| colspan="2"|1.24±0.1 g/cm3
|-
| [[Enthalpy of vaporization]]
| colspan="2"|63.93±3.0 kJ/mol
|-
| [[Flash point]]
| colspan="2"|172.0±27.9 °C
|}

Artemisinin is a drug that is used to treat malaria. This compound is obtained from the leaves of the shrub ‘Artemesia annua’, which is cultivated in China (ref 1). Artemisinin affects the malarial parasite, which is responsible for the malaria disease in humans. The drug has no significant side effects and reduces the malarial fever.

The information in the box on the right (containing the 2d structure, 3d structure, molecular weight etc...) was obtained from SciFinder Scholar (ref 2).

Artemisia has a great potential for being an effective drug to treat malaria, which is a disease that affects more than 300 million people a year (ref 3). Malaria kills about one million people a year (mainly young children), in sub-Saharan Africa and south Asia. Clinical trials in some countries (such as India, Indonesia, and Vietnam) have that over 90% of patients have recovered from malaria, when treated by using Artemisinin-based Combination Therapies (ACTs).

The Artemisia plant has been used in Chinese medicine for over a thousand years, but only in the 1960’s when military scientists in China started to analyse the large variety of Chinese traditional medicines, to find a substance that will protect the Chinese military from the malaria disease. The researchers were able to extract a chemical known as Artemisinin, which had the desired anti-malarial properties. The step from the 1960’s was to modify Artemisinin to become more potent against malaria, because the malaria parasite can evolve (by natural selection) to survive in the presence of Artemisinin. This has lead to scientists modifying the groups in Artemisinin, to produce a more potent drug.

==References==

1) http://www.medterms.com/script/main/art.asp?articlekey=24010

2) SciFinder Scholar

3) Economist 11/20/2004, Vol. 373 Issue 8402, p81

It:Artemisinin

2006-11-27T15:17:38Z

Vl105:

It:Artemisinin

2006-11-27T14:59:35Z

Vl105: added the right structure of Artemisinin, and added some data from reference

File:Vlartemisinin.JPG

2006-11-27T14:23:41Z

Vl105: right structure of artemisinin

right structure of artemisinin

It:Artemisinin

2006-11-24T16:16:31Z

Vl105:

Artemisinin is a drug that is used to treat malaria. This compound is obtained from the leaves of the shrub ‘Artemsisia annua’, which is cultivated in China (ref 1). Artemisinin affects the malarial parasite, which is responsible for the malaria disease in humans. The drug has no significant side effects and reduces the malarial fever.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Vl2Dartemisinin.JPG|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 O 0 -1.296 1.980 1.242 0.00 0.00 O+0
ATOM 2 C 0 -1.120 1.990 -0.176 0.00 0.00 C+0
ATOM 3 C 0 0.346 2.281 -0.521 0.00 0.00 C+0
ATOM 4 C 0 1.290 1.146 -0.272 0.00 0.00 C+0
ATOM 5 C 0 1.949 0.920 -1.634 0.00 0.00 C+0
ATOM 6 C 0 2.452 1.481 0.615 0.00 0.00 C+0
ATOM 7 C 0 3.343 0.492 0.851 0.00 0.00 C+0
ATOM 8 C 0 3.026 -0.814 0.208 0.00 0.00 C+0
ATOM 9 O 0 3.875 -1.504 -0.324 0.00 0.00 O+0
ATOM 10 C 0 1.591 -1.209 0.267 0.00 0.00 C+0
ATOM 11 C 0 0.722 -0.199 0.067 0.00 0.00 C+0
ATOM 12 C 0 -0.735 -0.390 0.221 0.00 0.00 C+0
ATOM 13 O 0 -1.373 -1.622 -0.156 0.00 0.00 O+0
ATOM 14 C 0 -2.707 -1.340 -0.229 0.00 0.00 C+0
ATOM 15 O 0 -3.603 -2.131 -0.053 0.00 0.00 O+0
ATOM 16 C 0 -2.882 0.139 -0.569 0.00 0.00 C+0
ATOM 17 C 0 -3.594 0.874 0.568 0.00 0.00 C+0
ATOM 18 C 0 -1.441 0.620 -0.748 0.00 0.00 C+0
ATOM 19 C 0 1.147 -2.623 0.545 0.00 0.00 C+0
ATOM 20 H 0 -1.039 2.857 1.561 0.00 0.00 H+0
ATOM 21 H 0 -1.766 2.744 -0.627 0.00 0.00 H+0
ATOM 22 H 0 0.404 2.551 -1.575 0.00 0.00 H+0
ATOM 23 H 0 0.674 3.137 0.068 0.00 0.00 H+0
ATOM 24 H 0 2.563 1.784 -1.888 0.00 0.00 H+0
ATOM 25 H 0 2.575 0.029 -1.591 0.00 0.00 H+0
ATOM 26 H 0 1.178 0.786 -2.393 0.00 0.00 H+0
ATOM 27 H 0 2.572 2.465 1.045 0.00 0.00 H+0
ATOM 28 H 0 4.222 0.638 1.461 0.00 0.00 H+0
ATOM 29 H 0 -1.012 -0.152 1.247 0.00 0.00 H+0
ATOM 30 H 0 -3.429 0.257 -1.504 0.00 0.00 H+0
ATOM 31 H 0 -3.018 0.768 1.487 0.00 0.00 H+0
ATOM 32 H 0 -3.686 1.931 0.316 0.00 0.00 H+0
ATOM 33 H 0 -4.587 0.448 0.711 0.00 0.00 H+0
ATOM 34 H 0 -1.122 0.539 -1.787 0.00 0.00 H+0
ATOM 35 H 0 2.022 -3.257 0.686 0.00 0.00 H+0
ATOM 36 H 0 0.537 -2.641 1.448 0.00 0.00 H+0
ATOM 37 H 0 0.562 -2.992 -0.297 0.00 0.00 H+0
CONECT 1 2 20 0 0 NONE 42
CONECT 2 1 18 3 21 NONE 43
CONECT 3 2 4 22 23 NONE 44
CONECT 4 3 11 5 6 NONE 45
CONECT 5 4 24 25 26 NONE 46
CONECT 6 4 7 27 0 NONE 47
CONECT 7 6 8 28 0 NONE 48
CONECT 8 7 9 10 0 NONE 49
CONECT 9 8 0 0 0 NONE 50
CONECT 10 8 11 19 0 NONE 51
CONECT 11 10 4 12 0 NONE 52
CONECT 12 11 18 13 29 NONE 53
CONECT 13 12 14 0 0 NONE 54
CONECT 14 13 15 16 0 NONE 55
CONECT 15 14 0 0 0 NONE 56
CONECT 16 14 17 18 30 NONE 57
CONECT 17 16 31 32 33 NONE 58
CONECT 18 16 2 12 34 NONE 59
CONECT 19 10 35 36 37 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Molecular weight]]
| colspan="2"| 262.301 g/mol
|-
| [[Molecular Formula]]
|colspan="2"| C15H18O4
|-
| [[SMILES]]
| colspan="2"| CC1C2C(CC3(C=CC(=O)C(=C3C2OC1=O)C)C)O
|}

==References==

1) http://www.medterms.com/script/main/art.asp?articlekey=24010

It:Artemisinin

2006-11-24T16:16:01Z

Vl105: added SMILES

Artemisinin is a drug that is used to treat malaria. This compound is obtained from the leaves of the shrub ‘Artemsisia annua’, which is cultivated in China (ref 1). Artemisinin affects the malarial parasite, which is responsible for the malaria disease in humans. The drug has no significant side effects and reduces the malarial fever.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Vl2Dartemisinin.JPG|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 O 0 -1.296 1.980 1.242 0.00 0.00 O+0
ATOM 2 C 0 -1.120 1.990 -0.176 0.00 0.00 C+0
ATOM 3 C 0 0.346 2.281 -0.521 0.00 0.00 C+0
ATOM 4 C 0 1.290 1.146 -0.272 0.00 0.00 C+0
ATOM 5 C 0 1.949 0.920 -1.634 0.00 0.00 C+0
ATOM 6 C 0 2.452 1.481 0.615 0.00 0.00 C+0
ATOM 7 C 0 3.343 0.492 0.851 0.00 0.00 C+0
ATOM 8 C 0 3.026 -0.814 0.208 0.00 0.00 C+0
ATOM 9 O 0 3.875 -1.504 -0.324 0.00 0.00 O+0
ATOM 10 C 0 1.591 -1.209 0.267 0.00 0.00 C+0
ATOM 11 C 0 0.722 -0.199 0.067 0.00 0.00 C+0
ATOM 12 C 0 -0.735 -0.390 0.221 0.00 0.00 C+0
ATOM 13 O 0 -1.373 -1.622 -0.156 0.00 0.00 O+0
ATOM 14 C 0 -2.707 -1.340 -0.229 0.00 0.00 C+0
ATOM 15 O 0 -3.603 -2.131 -0.053 0.00 0.00 O+0
ATOM 16 C 0 -2.882 0.139 -0.569 0.00 0.00 C+0
ATOM 17 C 0 -3.594 0.874 0.568 0.00 0.00 C+0
ATOM 18 C 0 -1.441 0.620 -0.748 0.00 0.00 C+0
ATOM 19 C 0 1.147 -2.623 0.545 0.00 0.00 C+0
ATOM 20 H 0 -1.039 2.857 1.561 0.00 0.00 H+0
ATOM 21 H 0 -1.766 2.744 -0.627 0.00 0.00 H+0
ATOM 22 H 0 0.404 2.551 -1.575 0.00 0.00 H+0
ATOM 23 H 0 0.674 3.137 0.068 0.00 0.00 H+0
ATOM 24 H 0 2.563 1.784 -1.888 0.00 0.00 H+0
ATOM 25 H 0 2.575 0.029 -1.591 0.00 0.00 H+0
ATOM 26 H 0 1.178 0.786 -2.393 0.00 0.00 H+0
ATOM 27 H 0 2.572 2.465 1.045 0.00 0.00 H+0
ATOM 28 H 0 4.222 0.638 1.461 0.00 0.00 H+0
ATOM 29 H 0 -1.012 -0.152 1.247 0.00 0.00 H+0
ATOM 30 H 0 -3.429 0.257 -1.504 0.00 0.00 H+0
ATOM 31 H 0 -3.018 0.768 1.487 0.00 0.00 H+0
ATOM 32 H 0 -3.686 1.931 0.316 0.00 0.00 H+0
ATOM 33 H 0 -4.587 0.448 0.711 0.00 0.00 H+0
ATOM 34 H 0 -1.122 0.539 -1.787 0.00 0.00 H+0
ATOM 35 H 0 2.022 -3.257 0.686 0.00 0.00 H+0
ATOM 36 H 0 0.537 -2.641 1.448 0.00 0.00 H+0
ATOM 37 H 0 0.562 -2.992 -0.297 0.00 0.00 H+0
CONECT 1 2 20 0 0 NONE 42
CONECT 2 1 18 3 21 NONE 43
CONECT 3 2 4 22 23 NONE 44
CONECT 4 3 11 5 6 NONE 45
CONECT 5 4 24 25 26 NONE 46
CONECT 6 4 7 27 0 NONE 47
CONECT 7 6 8 28 0 NONE 48
CONECT 8 7 9 10 0 NONE 49
CONECT 9 8 0 0 0 NONE 50
CONECT 10 8 11 19 0 NONE 51
CONECT 11 10 4 12 0 NONE 52
CONECT 12 11 18 13 29 NONE 53
CONECT 13 12 14 0 0 NONE 54
CONECT 14 13 15 16 0 NONE 55
CONECT 15 14 0 0 0 NONE 56
CONECT 16 14 17 18 30 NONE 57
CONECT 17 16 31 32 33 NONE 58
CONECT 18 16 2 12 34 NONE 59
CONECT 19 10 35 36 37 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Molecular weight]]
| colspan="2"| 262.301 g/mol
|-
| [[Molecular Formula]]
|colspan="2"| C15H18O4
|-
| [[SMILES]]
| colspan="2"| CC1C2C(CC3(C=CC(=O)C(=C3C2OC1=O)C)C)O
|}

==References==

1) http://www.medterms.com/script/main/art.asp?articlekey=24010

It:Artemisinin

2006-11-24T15:49:52Z

Vl105:

Artemisinin is a drug that is used to treat malaria. This compound is obtained from the leaves of the shrub ‘Artemsisia annua’, which is cultivated in China (ref 1). Artemisinin affects the malarial parasite, which is responsible for the malaria disease in humans. The drug has no significant side effects and reduces the malarial fever.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Vl2Dartemisinin.JPG|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 O 0 -1.296 1.980 1.242 0.00 0.00 O+0
ATOM 2 C 0 -1.120 1.990 -0.176 0.00 0.00 C+0
ATOM 3 C 0 0.346 2.281 -0.521 0.00 0.00 C+0
ATOM 4 C 0 1.290 1.146 -0.272 0.00 0.00 C+0
ATOM 5 C 0 1.949 0.920 -1.634 0.00 0.00 C+0
ATOM 6 C 0 2.452 1.481 0.615 0.00 0.00 C+0
ATOM 7 C 0 3.343 0.492 0.851 0.00 0.00 C+0
ATOM 8 C 0 3.026 -0.814 0.208 0.00 0.00 C+0
ATOM 9 O 0 3.875 -1.504 -0.324 0.00 0.00 O+0
ATOM 10 C 0 1.591 -1.209 0.267 0.00 0.00 C+0
ATOM 11 C 0 0.722 -0.199 0.067 0.00 0.00 C+0
ATOM 12 C 0 -0.735 -0.390 0.221 0.00 0.00 C+0
ATOM 13 O 0 -1.373 -1.622 -0.156 0.00 0.00 O+0
ATOM 14 C 0 -2.707 -1.340 -0.229 0.00 0.00 C+0
ATOM 15 O 0 -3.603 -2.131 -0.053 0.00 0.00 O+0
ATOM 16 C 0 -2.882 0.139 -0.569 0.00 0.00 C+0
ATOM 17 C 0 -3.594 0.874 0.568 0.00 0.00 C+0
ATOM 18 C 0 -1.441 0.620 -0.748 0.00 0.00 C+0
ATOM 19 C 0 1.147 -2.623 0.545 0.00 0.00 C+0
ATOM 20 H 0 -1.039 2.857 1.561 0.00 0.00 H+0
ATOM 21 H 0 -1.766 2.744 -0.627 0.00 0.00 H+0
ATOM 22 H 0 0.404 2.551 -1.575 0.00 0.00 H+0
ATOM 23 H 0 0.674 3.137 0.068 0.00 0.00 H+0
ATOM 24 H 0 2.563 1.784 -1.888 0.00 0.00 H+0
ATOM 25 H 0 2.575 0.029 -1.591 0.00 0.00 H+0
ATOM 26 H 0 1.178 0.786 -2.393 0.00 0.00 H+0
ATOM 27 H 0 2.572 2.465 1.045 0.00 0.00 H+0
ATOM 28 H 0 4.222 0.638 1.461 0.00 0.00 H+0
ATOM 29 H 0 -1.012 -0.152 1.247 0.00 0.00 H+0
ATOM 30 H 0 -3.429 0.257 -1.504 0.00 0.00 H+0
ATOM 31 H 0 -3.018 0.768 1.487 0.00 0.00 H+0
ATOM 32 H 0 -3.686 1.931 0.316 0.00 0.00 H+0
ATOM 33 H 0 -4.587 0.448 0.711 0.00 0.00 H+0
ATOM 34 H 0 -1.122 0.539 -1.787 0.00 0.00 H+0
ATOM 35 H 0 2.022 -3.257 0.686 0.00 0.00 H+0
ATOM 36 H 0 0.537 -2.641 1.448 0.00 0.00 H+0
ATOM 37 H 0 0.562 -2.992 -0.297 0.00 0.00 H+0
CONECT 1 2 20 0 0 NONE 42
CONECT 2 1 18 3 21 NONE 43
CONECT 3 2 4 22 23 NONE 44
CONECT 4 3 11 5 6 NONE 45
CONECT 5 4 24 25 26 NONE 46
CONECT 6 4 7 27 0 NONE 47
CONECT 7 6 8 28 0 NONE 48
CONECT 8 7 9 10 0 NONE 49
CONECT 9 8 0 0 0 NONE 50
CONECT 10 8 11 19 0 NONE 51
CONECT 11 10 4 12 0 NONE 52
CONECT 12 11 18 13 29 NONE 53
CONECT 13 12 14 0 0 NONE 54
CONECT 14 13 15 16 0 NONE 55
CONECT 15 14 0 0 0 NONE 56
CONECT 16 14 17 18 30 NONE 57
CONECT 17 16 31 32 33 NONE 58
CONECT 18 16 2 12 34 NONE 59
CONECT 19 10 35 36 37 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Molecular weight]]
| colspan="2"| 262.301 g/mol
|-
| [[Molecular Formula]]
|colspan="2"| C15H18O4
|-
|}

==References==

1) http://www.medterms.com/script/main/art.asp?articlekey=24010

It:Artemisinin

2006-11-24T15:48:04Z

Vl105: added intro

Artemisinin is a drug that is used to treat malaria. This compound is obtained from the leaves of the shrub ‘Artemsisia annua’, which is cultivated in China (ref 1). Artemisinin affects the malarial parasite, which is responsible for the malaria disease in humans. The drug has no significant side effects and reduces the malarial fever.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Vl2Dartemisinin.JPG|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure of Artemisinin
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 O 0 -1.296 1.980 1.242 0.00 0.00 O+0
ATOM 2 C 0 -1.120 1.990 -0.176 0.00 0.00 C+0
ATOM 3 C 0 0.346 2.281 -0.521 0.00 0.00 C+0
ATOM 4 C 0 1.290 1.146 -0.272 0.00 0.00 C+0
ATOM 5 C 0 1.949 0.920 -1.634 0.00 0.00 C+0
ATOM 6 C 0 2.452 1.481 0.615 0.00 0.00 C+0
ATOM 7 C 0 3.343 0.492 0.851 0.00 0.00 C+0
ATOM 8 C 0 3.026 -0.814 0.208 0.00 0.00 C+0
ATOM 9 O 0 3.875 -1.504 -0.324 0.00 0.00 O+0
ATOM 10 C 0 1.591 -1.209 0.267 0.00 0.00 C+0
ATOM 11 C 0 0.722 -0.199 0.067 0.00 0.00 C+0
ATOM 12 C 0 -0.735 -0.390 0.221 0.00 0.00 C+0
ATOM 13 O 0 -1.373 -1.622 -0.156 0.00 0.00 O+0
ATOM 14 C 0 -2.707 -1.340 -0.229 0.00 0.00 C+0
ATOM 15 O 0 -3.603 -2.131 -0.053 0.00 0.00 O+0
ATOM 16 C 0 -2.882 0.139 -0.569 0.00 0.00 C+0
ATOM 17 C 0 -3.594 0.874 0.568 0.00 0.00 C+0
ATOM 18 C 0 -1.441 0.620 -0.748 0.00 0.00 C+0
ATOM 19 C 0 1.147 -2.623 0.545 0.00 0.00 C+0
ATOM 20 H 0 -1.039 2.857 1.561 0.00 0.00 H+0
ATOM 21 H 0 -1.766 2.744 -0.627 0.00 0.00 H+0
ATOM 22 H 0 0.404 2.551 -1.575 0.00 0.00 H+0
ATOM 23 H 0 0.674 3.137 0.068 0.00 0.00 H+0
ATOM 24 H 0 2.563 1.784 -1.888 0.00 0.00 H+0
ATOM 25 H 0 2.575 0.029 -1.591 0.00 0.00 H+0
ATOM 26 H 0 1.178 0.786 -2.393 0.00 0.00 H+0
ATOM 27 H 0 2.572 2.465 1.045 0.00 0.00 H+0
ATOM 28 H 0 4.222 0.638 1.461 0.00 0.00 H+0
ATOM 29 H 0 -1.012 -0.152 1.247 0.00 0.00 H+0
ATOM 30 H 0 -3.429 0.257 -1.504 0.00 0.00 H+0
ATOM 31 H 0 -3.018 0.768 1.487 0.00 0.00 H+0
ATOM 32 H 0 -3.686 1.931 0.316 0.00 0.00 H+0
ATOM 33 H 0 -4.587 0.448 0.711 0.00 0.00 H+0
ATOM 34 H 0 -1.122 0.539 -1.787 0.00 0.00 H+0
ATOM 35 H 0 2.022 -3.257 0.686 0.00 0.00 H+0
ATOM 36 H 0 0.537 -2.641 1.448 0.00 0.00 H+0
ATOM 37 H 0 0.562 -2.992 -0.297 0.00 0.00 H+0
CONECT 1 2 20 0 0 NONE 42
CONECT 2 1 18 3 21 NONE 43
CONECT 3 2 4 22 23 NONE 44
CONECT 4 3 11 5 6 NONE 45
CONECT 5 4 24 25 26 NONE 46
CONECT 6 4 7 27 0 NONE 47
CONECT 7 6 8 28 0 NONE 48
CONECT 8 7 9 10 0 NONE 49
CONECT 9 8 0 0 0 NONE 50
CONECT 10 8 11 19 0 NONE 51
CONECT 11 10 4 12 0 NONE 52
CONECT 12 11 18 13 29 NONE 53
CONECT 13 12 14 0 0 NONE 54
CONECT 14 13 15 16 0 NONE 55
CONECT 15 14 0 0 0 NONE 56
CONECT 16 14 17 18 30 NONE 57
CONECT 17 16 31 32 33 NONE 58
CONECT 18 16 2 12 34 NONE 59
CONECT 19 10 35 36 37 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[Molecular weight]]
| colspan="2"| 262.301 g/mol
|-
| [[Molecular Formula]]
|colspan="2"| C15H18O4
|-
|}

==References==

*http://www.medterms.com/script/main/art.asp?articlekey=24010

It:Artemisinin

2006-11-24T15:31:08Z

Vl105: added 2d and 3d structures of artemisinin

File:Vl2Dartemisinin.JPG

2006-11-24T15:18:17Z

Vl105: 2d structure of artemisinin

2d structure of artemisinin

It:projects

2006-11-24T15:12:54Z

Vl105: /* Supplemental Project Page */

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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)]]
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|-
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| bgcolor="#CCFF00" |11
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| bgcolor="#CCFF00" |13
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| bgcolor="#CCFF00" |14
| bgcolor="#66FF99" | [[it:Methoxsalen|Methoxsalen (Treatment of psoriasis)]]
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| bgcolor="#CCFF00" |15
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| bgcolor="#CCFF00" |17
| bgcolor="#CCFF00" | [[it:wilkinson|Wilkinson's catalyst]]
|-
| bgcolor="#CCFF00" |18
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|-
| bgcolor="#CCFF00" |19
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|-
| 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)]]
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| bgcolor="#CCFF00" |25
| bgcolor="#CCFF00" | [[it:Ceftriaxone|Ceftriaxone (Gonorrhoea)]]
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| bgcolor="#CCFF00" |26
| bgcolor="#66FF99" | [[it:Zithromycin|Zithromycin (anti-infective)]]
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| bgcolor="#CCFF00" |27
| bgcolor="#CCFF00" | [[it:Lipitor|Lipitor (Cholesterol reducing agent)]]
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| bgcolor="#CCFF00" |28
| bgcolor="#66FF99" | [[it:Cyameluric Acid|Cyameluric acid (Linus Pauling's last idea!)]]
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----
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It:Schwartz

2006-11-24T14:53:34Z

Vl105: doi of reaction scheme

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Schwartz Reagent
|-
! {{chembox header}} colspan="3" |Structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Schwartz_Reagent.JPG|Schwartz's Reagent]]
|-
! {{chembox header}} colspan="3" |3D structure
<jmol>
<jmolApplet>
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title1
title2
23 32 0 0 0 0 0 0 0 0999 V2000
0.4968 2.4426 -1.8773 Zr 0 0 0 0 0 0 0 0 0 1
2.1386 2.5155 -0.0069 C 0 0 1 0 0 0 0 0 0 2
0.8893 2.8016 0.5785 C 0 0 1 0 0 0 0 0 0 3
0.4392 4.0345 0.0856 C 0 0 1 0 0 0 0 0 0 4
1.4009 4.5239 -0.7980 C 0 0 1 0 0 0 0 0 0 5
2.4581 3.6019 -0.8408 C 0 0 1 0 0 0 0 0 0 6
1.3075 2.1266 -4.2373 C 0 0 1 0 0 0 0 0 0 7
2.3637 1.7885 -3.4062 C 0 0 2 0 0 0 0 0 0 8
2.0155 0.6537 -2.7061 C 0 0 2 0 0 0 0 0 0 9
0.7446 0.2636 -3.1093 C 0 0 2 0 0 0 0 0 0 10
0.3198 1.1821 -4.0620 C 0 0 2 0 0 0 0 0 0 11
-1.3981 1.1750 -0.8823 Cl 0 0 0 0 0 0 0 0 0 12
-0.4999 3.6324 -2.6415 H 0 0 0 0 0 0 0 0 0 13
2.7373 1.6100 0.1615 H 0 0 0 0 0 0 0 0 0 14
0.3782 2.1727 1.3172 H 0 0 0 0 0 0 0 0 0 15
-0.5084 4.5050 0.3479 H 0 0 0 0 0 0 0 0 0 16
1.3481 5.4625 -1.3655 H 0 0 0 0 0 0 0 0 0 17
3.3834 3.6763 -1.4290 H 0 0 0 0 0 0 0 0 0 18
1.2659 3.0120 -4.9152 H 0 0 0 0 0 0 0 0 0 19
3.3152 2.3417 -3.3261 H 0 0 0 0 0 0 0 0 0 20
2.6389 0.1300 -1.9509 H 0 0 0 0 0 0 0 0 0 21
0.1603 -0.6100 -2.7365 H 0 0 0 0 0 0 0 0 0 22
-0.6338 1.1620 -4.5991 H 0 0 0 0 0 0 0 0 0 23
1 2 1 0 0 0
2 3 4 0 0 0
3 1 1 0 0 0
4 1 1 0 0 0
5 1 1 0 0 0
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7 1 1 0 0 0
8 1 1 0 0 0
9 1 1 0 0 0
10 1 1 0 0 0
11 1 1 0 0 0
12 1 1 0 0 0
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17 5 1 0 0 0
18 6 1 0 0 0
19 7 1 0 0 0
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22 10 1 0 0 0
23 11 1 0 0 0
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3 4 4 0 0 0
4 5 4 0 0 0
5 6 4 0 0 0
7 8 4 0 0 0
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8 9 4 0 0 0
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M END</inlineContents>
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|-
! {{chembox header}} colspan="3" | General
|-
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|Bis(η5-cyclopentadienyl)-
zirconium(IV) chloride hydride
|-
| colspan="1" |Synonyms
| colspan="2" |Zirconocene chloride hydride
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C<sub>10</sub>H<sub>11</sub>ClZr
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" |257.87 g/mol
|-
| colspan="1" |Appearance
| colspan="2" |Off-white solid
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |37342-97-5
|-
| colspan="1" |[http://en.wikipedia.org/wiki/EC-No EC number]
| colspan="2" |253-479-5
|-
! {{chembox header}} colspan="3"| Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] and [http://en.wikipedia.org/wiki/Phase_%28matter%29 Phase]
| colspan="2" |g/cm<sup>3</sup>, solid
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility] in [http://en.wikipedia.org/wiki/Water_%28molecule%29 water]
| colspan="2" |
|-
| Other solvents
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |>300°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Standard_enthalpy_change_of_formation Δ''H''<sub>''f''</sub><sup><s>o</s></sup><sub>solid</sub>]
| colspan="2" |-314.8 ± 3.9 kJ/mol
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |?
|-
! {{chembox header}} colspan="3"| Structure
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| colspan="2"|
|-
| [http://en.wikipedia.org/wiki/Dipole#Molecular_dipoles Dipole moment]
| colspan="2" |? [http://en.wikipedia.org/wiki/Debye D]
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| [http://en.wikipedia.org/wiki/Material_safety_data_sheet MSDS]
| colspan="2" |[http://www.sigmaaldrich.com/cgi-bin/hsrun/Suite7/Suite/HAHTpage/Suite.HsSigmaAdvancedSearch.formAction Sigma-Aldrich MSDS]
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
*Highly flammable
*Contact with water
liberates flammable gases
*Causes burns
|-
| [http://en.wikipedia.org/wiki/NFPA_704 NFPA 704]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Flash_point Flash point]
| colspan="2" |? °C
|-
| [http://en.wikipedia.org/wiki/Risk_and_Safety_Statements R/S statement]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/RTECS RTECS] number
| colspan="2" |
|-
! {{chembox header}} colspan="3" | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| Structure and properties
| colspan="2" |
|-
| Thermodynamic data
| colspan="2" |
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [http://www.sigmaaldrich.com/spectra/rair/RAIR004389.PDF FT-IR Raman], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Related compounds
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}
== Introduction ==
Schwartz's Reagent is the common name for bis(cyclopentadienyl)zirconium(IV) chloride hydride). The Schwartz Reagent is a commercially available chemical with a structural formula of Cp<sub>2</sub>Zr(H)Cl. It is used in the hydrozirconation of alkynes and alkenes. It is used due to:
*It's wide availability
*The mild conditions that are required to make the reaction happen
*It's efficiency
*And it's excellent regio- and stereochemical selectivity

==Background==

The first organochlorobis(cyclopentadienyl)zirconium(W)complex was prepared by Wailes, Weigold and Bell 25 years ago. Ever since, these organometallics have become important members in the field of synthetic strategy and tactics.because of the formations of carbon-carbon and carbon-heteroatom bond.Although the polarization of the carbon-zirconium bond is similar to Grignard reagents, the bulky cyclopentadienyl groups prevent the attack of many organic electrophiles due to steric crowding around the Zr atom. The resulting functional group tolerance of organozirconocenes is useful for the preparation of the organometallic species, but this low reactivity must be overcome for subsequent selective carbon-carbon bond formations. Therefore, much of the development of organozirconocenes focuses on indirect reaction pathways involving transmetalation or activation by ligand.

==Preparation of Schwartz's Reagent==
The chemical can be purchased or prepared by reduction of zirconocene dichloride with lithium aluminum hydride.

[[Image:CV9P0162.gif]]

Zirconocene dichloride is added under argon to a flask equipped with a magnetic stirring bar, followed by addition of dry tetrahydrofuran. The solid is dissolved by heating gently with a heat gun. To the solution at 35°C, over a 45-min period, a filtered solution of lithium aluminum hydride in ethyl ether is added dropwise. (Crystallization occurs if the temperature is allowed to fall below 35°C. The reaction can be conducted successfully even if a small amount of solid forms.)The suspension is then stirred at room temperature. The mixture is then filtered under argon using a "D" frit. The resulting white solid is washed with tetrahydrofuran methylene chloride and then with ether.

[[Image:Untitled.GIF]]

==Examples in Organic Synthesis==

===Triethylborane-induced radical reaction with Schwartz Reagent:===

(References from Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; J. Am. Chem. Soc.; 2001; 123(13); 3137-3138)
[[Image:Schwartz20figure202.gif]]

===Stereo- and regiocontrolled synthesis of branched trisubstituted conjugated dienes by palladium(0)-catalyzed cross-coupling reaction:===

(References from Panek, J. S.; Hu, T.; J. Org. Chem.; 1997; 62(15); 4912-4913)
[[Image:Schwartz20figure203.gif]]

==Mechanism of the Hydrozirconation reaction (reaction of an olefin with Cp<sub>2</sub>Zr(H)Cl)==
In this reaction the insertion of either a terminal or internal olefin gives the same product, B. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below:

[[Image:Hydrozirconation.gif]]

==Properties of Schwartz Reagent==

===Selectivity:===

Bulk of [Zr] complex ensures that it will attack least hindered position of olefin or addition to internal olefin followed by metal migration until it reaches the end:

[[Image:Picture2.png]]

These are the thermodynamic products of the reaction and arise primarily from steric interaction with the Cp ring.

=== Electrophilic cleavage of alkyl zirconium bond: ===
This reaction is very facile and forms product in high yield:
[[Image:Picture3.png]]

==Hydrozirconation of 1-alkynes==

This reaction is important in chemistry because the product that is synthesised from the acetylene (e.g. 1-alkynes) is regioselectively controlled. This gives rise to greater yields of products with the selectively required stereochemistry. So a range of diverse compounds can be derived from mono-substitued acetylenes, via this reaction.

[[Image:Vlzirconation.gif]]

The above {{doi-inline|10.1021/ja00176a079|reaction scheme}} requires 4 steps. The second and third steps require a very cool temperature of -78<sup>o</sup>C, to prevent unwanted side reactions which would produce unwanted products.

==References==

1. {{doi-inline|10.1021/ja00176a079|reaction scheme}}

2. http://people.bu.edu/jaylowe/Named%20reagents/S/Schwartz/Schwartz.htm

3. http://orgchem.chem.uconn.edu/namereact/schwartz.html

4. http://www.answers.com/topic/schwartz-s-reagent

5. http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV9P0162

6. http://pubs.acs.org/cen/nlw/8216sci1.html

It:Lignocaine

2006-11-24T13:20:46Z

Vl105: added picture of the two similar bottles

Lignocaine is a local anaesthetic drug especially used in dentistry. Discovered by N.Lofgren and B.Lundqvist in the 1940s, it has been very successful due to it's low neurotoxicity when compared with other local anaesthetics.
It has found uses also in the treatment of Arrhythmias eg: problems of the electrical system of the heart, causing it to pump less efficiently.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Lignocaine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Lignocaine.gif|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <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>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
</inlineContents>
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</jmol>
|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[CA Index Name]]
| colspan="2"| Acetamide,
2-(diethylamino)-N-(2,6-dimethylphenyl)- (9CI)
|-
| [[Commercial Names]]
|colspan="2"| Xylocaine (Astra)
Emla (Astra)

Instillagel (Cliniflex)

Laryng-o-jet (IMS)
|-
| [[Chemical formula|Molecular formula]]
| colspan="2" | C<sub>14</sub>H<sub>22</sub>N<sub>2</sub>O
|-
| [[Molar mass]]
| colspan="2" |234.2 g/mol
|-
| [[CAS registry number|CAS number]]
| colspan="2" | 137-58-6
|-
| [[Appearance]]
| colspan="2" | colourless crystalline powder
|-
! {{chembox header}} colspan="3"| Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| colspan="2" | g/cm
|-
| [[Solubility]] in [[Water_(molecule)|water (ph=7)]]
| colspan="2" | Soluble (15 g/L)
|-
| [[Melting point]]
| colspan="2" | 159-160 °C
|-
| [[Boiling point]]
| colspan="2" | 68.5 °C
|-
| [[Acid dissociation constant|Acidity]] (p''Ka'') 
| colspan="2" | 7.8
|-
| [[Flash Point]]
| colspan="2" | 166.0±24.6 °C
|-
| [[Enthalpy of Vaporization]]
| colspan="2" | 59.55±3.0 kJ/mol
|-
! {{chembox header}} colspan="3"| Structure
|-
| [[Crystal structure]] 
| colspan="2"|
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| colspan="2" |? [[Debye|D]]
|-
| {{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>
|-
|}

==Synthesis==
[[Image:synthesisoflinocaine.gif|200px{{PAGENAME}}]]

==IR spectrum of lidocaine==
[[Image:vlirlidocaine.gif]]

Above: The IR spectrum of lidocaine

==Mass spectrum of lidocaine==

[[Image:vlmasslidocaine.gif]]

Above: The mass spectrum of lidocaine

==What does Lignocaine do?==
• Stabilises neuronal membrane, prevents the initiation and transmission of nerve impulses

• Antiarrhythmic effect by increasing the electrical stimulation threshold of the ventricle during diastole

• Depresses slow spontaneous depolarisation (ie decreases automaticity)

• Increases period of effective refractory period

• Potent suppressor of abnormal cardiac activity

• Blocks activated & inactivated sodium channels

• Suppresses activity of depolarised, arrhythmogenic tissues while minimally interfering with the electrical activity of normal tissues: therefore is effective in suppressing arrhythmias associated with depolarisation [eg ischaemia, digitalis toxicity] but is relatively ineffective against arrhythmias occurring in normally polarised cells [eg AF & Af]

• Lignocaine can act as a local anaesthetic by preventing sodium ions flowing through the nerve membrane, so this stops nerve impulses along nerve fibres ([http://www.medsafe.govt.nz/Profs/Datasheet/x/Xyloproctointsupp.htm]), without loss of consciousness.

[[Image:Vlanaesthetic.jpg|thumb|anaesthetic mechanism [http://www.frca.co.uk/article.aspx?articleid=100505])]]

The amide group (-CONH-) in Lignocaine allows it to act in the sodium channels of the nerve membrane.
When Lignocaine is applied on the skin, the compound is absorbed by the mucus membrane. The rate of absorption is dependent on the concentration of the dose. If Lignocaine is injected into the vein, it takes about 2 hours for half the amount of Lignocaine injected to metabolise.

The amide bond in lignocaine is more stronger than the ester linkage in drugs that contain ester links. So the amide type drugs such as lignocaine are more stable when dissolved in a solvent such as water, and can be stored for longer.
Lignocaine rarely causes allergic reactions in comparison to drugs which contains ester links. This is due to most of the ester type drugs causing the production of para-aminobenzoate (PABA) during metabolism, which causes the allergic reactions.

The natural pH of the human body is about 7.4, which causes most local anaesthetics to become more ionised than unionised. The pKa of Lignocaine is 7.9([http://www.frca.co.uk/article.aspx?articleid=100505]), which means that about 25% of the drug is unionised at pH 7.4. The Lignocaine must enter cells by passing the lipid membrane, which allows the unionised form of local anaesthetics to reach the target cells more quickly.

Lignocaine is metabolised in the liver by amidases, which hydrolyses the amide bond in Lignocaine. This process is slow, and so the drug can accumulate when further doses are taken by the patient. Lignocaine will act as an antiarrhythmic to stop irregular heart beat.

• In the US, patches containing lidocaine are marketed under the name LIDODERM®. These skin patches are used to relieve pain from Post-Herpetic Neralgia (the tingling pains also known as post-shingles pain). The adhesive patch contains 700mg of licocaine, which is enough to penetrate the skin to relieve the pain, but not enought to block the pain sensory receptors. The graph below, shows the average concentration of lidocaine in the blood of 15 normal, healthy volunteers:

[[Image:vlgraphlidocaine.gif]]

The graph shows that the concentration of lidocaine peaks at about the 12 hours mark, and then falls.
3 patches were applied at the same time for 3 consecutive days.
The concentrations of lidocaine in the blood, binds to mainly the plasma protein, alpha-1-acid glycoprotein.
At high plasma concentrations, lidocaine binds to the plasma protein concentration dependently.
Lidocaine can cross the placenta barrier and blood-brain barrier, by passive diffusion.

==Uses==

Lignocaine acts by provisionally blocking conduction over the nerve fibers.

When used in concentrations of 2-4% it produces a surface anaesthesia. Commonly injected at 1%, it has a rapid onset and a half life of about 90- 120 minutes.
It is commonly mixed with adrenaline in order to limit the bleeding, thus becoming a good face or scalp anaesthetic.

Lignocaine is also classified as a Class Ib antiarrhythmic agent.

==Contraindications==

Possible side effects:

• visual disturbances

• convulsions

• hypotension

• agitation

• deteriorating conscious level

• heart failure - negatively inotropic

• bradycardia - asystole

• left ventricular failure

An overdosage of lignocaine can result in convulsions, twitching and psychosis.

== Symptoms of allergic reaction to Lignocaine==

• Cough

• Difficulty swallowing or tongue swelling

• Dizziness or fainting; hives or swelling of eyelids, face or lips

• Itching or skin rash

• Stuffy nose

• Chest tightness

• Shortness of breath

• Troubled breathing or wheezing

== Signs of too much medicine being absorbed into the body ==
• Blurred or double vision

• Confusion

• Dizziness

• Light-headedness or drowsiness

• Feeling hot, cold, or numb

• Muscle twitching or trembling

• Nausea or vomiting

• Ringing or buzzing in the ears

• Shortness of breath or trouble breathing

• Unusual excitement

• Nervousness or restlessness

• Unusual tiredness or weakness

(The above side effects may occur if the medicine is used too often, applied to broken or inflamed skin, applied to very large areas, or kept on the skin too long.)

• In Australia, a mixture of Lignocaine and Chlorhexidine is marketed as a product called ‘Chlorhexidine and Lignocaine Mouth Paint W.C.H’. This product is used for teething pains that young children get when their teeth emerge from their gums. The children rinse the solution in their mouths, to alleviate the teething pains.

[[Image:Vltwobottles.JPG]]

But, this product was sold in a bottle that was identical (except the label sticker) to a Paracetamol containing product, which reduces mild pain (when ingested orally). A study showed that there were cases where children had mistakenly ingested the bottle containing Lignocaine and Chlorhexidine, while thinking it was Paracetamol.{{doi-inline|10.1111/j.1440-1754.2006.00871.x|Article of toxicity in children due to mouth paint ingestion}}.

The Lignocaine and Chlorhexidine ingested caused toxic effects, as Lignocaine can be toxic if too much is ingested, which in the case of the mouth paint, the concentration of Lignocaine was 200mg per 10ml, and 5mg of Chlorhexidine per 10ml. Chlorhexidine is an antiseptic, that act as an antimicrobial agent on the teeth and gums to kill pathogens.

Children, who had taken under 6mg of Lignocaine per every kilogram of their body weight, were safe to be discharged from hospital. There were children who have taken doses of more than 6mg/ kg, which caused symptoms such as vomiting, and so required further observation in a hospital. Severe toxicity appeared in children who had taken doses of more than 15mg/ kg, such as seizures for a definite length of time (e.g. 1 h), and then recovered.

==References==
http://www.themediweb.net/pharmacy/Lignocaine.htm

http://www.elephantcare.org/Drugs/lidocain.htm

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=IR&Large=on

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=Mass&Large=on

http://www.perfusion.com.au/CCP/Pharmacology/lignocaine.htm

http://pharmacypractice.netfirms.com/kinetics/19/

http://www.healthtouch.com/bin/EContent_HT/drugShowLfts.asp?fname=usp0778.htm&title=Lignocaine&cid=HT

http://www.lidoderm.com/

http://www.medsafe.govt.nz/Profs/Datasheet/x/Xyloproctointsupp.htm

http://www.frca.co.uk/article.aspx?articleid=100505

{{doi-inline|10.1111/j.1440-1754.2006.00871.x|Article of toxicity in children due to mouth paint ingestion}}.

File:Vltwobottles.JPG

2006-11-24T13:17:05Z

Vl105: picture of the two similar bottles

picture of the two similar bottles

It:Lignocaine

2006-11-24T13:05:27Z

Vl105: added info about toxicity of lignocaine in children

Lignocaine is a local anaesthetic drug especially used in dentistry. Discovered by N.Lofgren and B.Lundqvist in the 1940s, it has been very successful due to it's low neurotoxicity when compared with other local anaesthetics.
It has found uses also in the treatment of Arrhythmias eg: problems of the electrical system of the heart, causing it to pump less efficiently.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Lignocaine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Lignocaine.gif|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <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>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
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[CA Index Name]]
| colspan="2"| Acetamide,
2-(diethylamino)-N-(2,6-dimethylphenyl)- (9CI)
|-
| [[Commercial Names]]
|colspan="2"| Xylocaine (Astra)
Emla (Astra)

Instillagel (Cliniflex)

Laryng-o-jet (IMS)
|-
| [[Chemical formula|Molecular formula]]
| colspan="2" | C<sub>14</sub>H<sub>22</sub>N<sub>2</sub>O
|-
| [[Molar mass]]
| colspan="2" |234.2 g/mol
|-
| [[CAS registry number|CAS number]]
| colspan="2" | 137-58-6
|-
| [[Appearance]]
| colspan="2" | colourless crystalline powder
|-
! {{chembox header}} colspan="3"| Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| colspan="2" | g/cm
|-
| [[Solubility]] in [[Water_(molecule)|water (ph=7)]]
| colspan="2" | Soluble (15 g/L)
|-
| [[Melting point]]
| colspan="2" | 159-160 °C
|-
| [[Boiling point]]
| colspan="2" | 68.5 °C
|-
| [[Acid dissociation constant|Acidity]] (p''Ka'') 
| colspan="2" | 7.8
|-
| [[Flash Point]]
| colspan="2" | 166.0±24.6 °C
|-
| [[Enthalpy of Vaporization]]
| colspan="2" | 59.55±3.0 kJ/mol
|-
! {{chembox header}} colspan="3"| Structure
|-
| [[Crystal structure]] 
| colspan="2"|
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| colspan="2" |? [[Debye|D]]
|-
| {{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>
|-
|}

==Synthesis==
[[Image:synthesisoflinocaine.gif|200px{{PAGENAME}}]]

==IR spectrum of lidocaine==
[[Image:vlirlidocaine.gif]]

Above: The IR spectrum of lidocaine

==Mass spectrum of lidocaine==

[[Image:vlmasslidocaine.gif]]

Above: The mass spectrum of lidocaine

==What does Lignocaine do?==
• Stabilises neuronal membrane, prevents the initiation and transmission of nerve impulses

• Antiarrhythmic effect by increasing the electrical stimulation threshold of the ventricle during diastole

• Depresses slow spontaneous depolarisation (ie decreases automaticity)

• Increases period of effective refractory period

• Potent suppressor of abnormal cardiac activity

• Blocks activated & inactivated sodium channels

• Suppresses activity of depolarised, arrhythmogenic tissues while minimally interfering with the electrical activity of normal tissues: therefore is effective in suppressing arrhythmias associated with depolarisation [eg ischaemia, digitalis toxicity] but is relatively ineffective against arrhythmias occurring in normally polarised cells [eg AF & Af]

• Lignocaine can act as a local anaesthetic by preventing sodium ions flowing through the nerve membrane, so this stops nerve impulses along nerve fibres ([http://www.medsafe.govt.nz/Profs/Datasheet/x/Xyloproctointsupp.htm]), without loss of consciousness.

[[Image:Vlanaesthetic.jpg|thumb|anaesthetic mechanism [http://www.frca.co.uk/article.aspx?articleid=100505])]]

The amide group (-CONH-) in Lignocaine allows it to act in the sodium channels of the nerve membrane.
When Lignocaine is applied on the skin, the compound is absorbed by the mucus membrane. The rate of absorption is dependent on the concentration of the dose. If Lignocaine is injected into the vein, it takes about 2 hours for half the amount of Lignocaine injected to metabolise.

The amide bond in lignocaine is more stronger than the ester linkage in drugs that contain ester links. So the amide type drugs such as lignocaine are more stable when dissolved in a solvent such as water, and can be stored for longer.
Lignocaine rarely causes allergic reactions in comparison to drugs which contains ester links. This is due to most of the ester type drugs causing the production of para-aminobenzoate (PABA) during metabolism, which causes the allergic reactions.

The natural pH of the human body is about 7.4, which causes most local anaesthetics to become more ionised than unionised. The pKa of Lignocaine is 7.9([http://www.frca.co.uk/article.aspx?articleid=100505]), which means that about 25% of the drug is unionised at pH 7.4. The Lignocaine must enter cells by passing the lipid membrane, which allows the unionised form of local anaesthetics to reach the target cells more quickly.

Lignocaine is metabolised in the liver by amidases, which hydrolyses the amide bond in Lignocaine. This process is slow, and so the drug can accumulate when further doses are taken by the patient. Lignocaine will act as an antiarrhythmic to stop irregular heart beat.

• In the US, patches containing lidocaine are marketed under the name LIDODERM®. These skin patches are used to relieve pain from Post-Herpetic Neralgia (the tingling pains also known as post-shingles pain). The adhesive patch contains 700mg of licocaine, which is enough to penetrate the skin to relieve the pain, but not enought to block the pain sensory receptors. The graph below, shows the average concentration of lidocaine in the blood of 15 normal, healthy volunteers:

[[Image:vlgraphlidocaine.gif]]

The graph shows that the concentration of lidocaine peaks at about the 12 hours mark, and then falls.
3 patches were applied at the same time for 3 consecutive days.
The concentrations of lidocaine in the blood, binds to mainly the plasma protein, alpha-1-acid glycoprotein.
At high plasma concentrations, lidocaine binds to the plasma protein concentration dependently.
Lidocaine can cross the placenta barrier and blood-brain barrier, by passive diffusion.

==Uses==

Lignocaine acts by provisionally blocking conduction over the nerve fibers.

When used in concentrations of 2-4% it produces a surface anaesthesia. Commonly injected at 1%, it has a rapid onset and a half life of about 90- 120 minutes.
It is commonly mixed with adrenaline in order to limit the bleeding, thus becoming a good face or scalp anaesthetic.

Lignocaine is also classified as a Class Ib antiarrhythmic agent.

==Contraindications==

Possible side effects:

• visual disturbances

• convulsions

• hypotension

• agitation

• deteriorating conscious level

• heart failure - negatively inotropic

• bradycardia - asystole

• left ventricular failure

An overdosage of lignocaine can result in convulsions, twitching and psychosis.

== Symptoms of allergic reaction to Lignocaine==

• Cough

• Difficulty swallowing or tongue swelling

• Dizziness or fainting; hives or swelling of eyelids, face or lips

• Itching or skin rash

• Stuffy nose

• Chest tightness

• Shortness of breath

• Troubled breathing or wheezing

== Signs of too much medicine being absorbed into the body ==
• Blurred or double vision

• Confusion

• Dizziness

• Light-headedness or drowsiness

• Feeling hot, cold, or numb

• Muscle twitching or trembling

• Nausea or vomiting

• Ringing or buzzing in the ears

• Shortness of breath or trouble breathing

• Unusual excitement

• Nervousness or restlessness

• Unusual tiredness or weakness

(The above side effects may occur if the medicine is used too often, applied to broken or inflamed skin, applied to very large areas, or kept on the skin too long.)

• In Australia, a mixture of Lignocaine and Chlorhexidine is marketed as a product called ‘Chlorhexidine and Lignocaine Mouth Paint W.C.H’. This product is used for teething pains that young children get when their teeth emerge from their gums. The children rinse the solution in their mouths, to alleviate the teething pains.

But, this product was sold in a bottle that was identical (except the label sticker) to a Paracetamol containing product, which reduces mild pain (when ingested orally). A study showed that there were cases where children had mistakenly ingested the bottle containing Lignocaine and Chlorhexidine, while thinking it was Paracetamol.{{doi-inline|10.1111/j.1440-1754.2006.00871.x|Article of toxicity in children due to mouth paint ingestion}}.

The Lignocaine and Chlorhexidine ingested caused toxic effects, as Lignocaine can be toxic if too much is ingested, which in the case of the mouth paint, the concentration of Lignocaine was 200mg per 10ml, and 5mg of Chlorhexidine per 10ml. Chlorhexidine is an antiseptic, that act as an antimicrobial agent on the teeth and gums to kill pathogens.

Children, who had taken under 6mg of Lignocaine per every kilogram of their body weight, were safe to be discharged from hospital. There were children who have taken doses of more than 6mg/ kg, which caused symptoms such as vomiting, and so required further observation in a hospital. Severe toxicity appeared in children who had taken doses of more than 15mg/ kg, such as seizures for a definite length of time (e.g. 1 h), and then recovered.

==References==
http://www.themediweb.net/pharmacy/Lignocaine.htm

http://www.elephantcare.org/Drugs/lidocain.htm

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=IR&Large=on

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=Mass&Large=on

http://www.perfusion.com.au/CCP/Pharmacology/lignocaine.htm

http://pharmacypractice.netfirms.com/kinetics/19/

http://www.healthtouch.com/bin/EContent_HT/drugShowLfts.asp?fname=usp0778.htm&title=Lignocaine&cid=HT

http://www.lidoderm.com/

http://www.medsafe.govt.nz/Profs/Datasheet/x/Xyloproctointsupp.htm

http://www.frca.co.uk/article.aspx?articleid=100505

{{doi-inline|10.1111/j.1440-1754.2006.00871.x|Article of toxicity in children due to mouth paint ingestion}}.

It:Lignocaine

2006-11-09T10:58:20Z

Vl105:

Lignocaine is a local anaesthetic drug especially used in dentistry. Discovered by N.Lofgren and B.Lundqvist in the 1940s, it has been very successful due to it's low neurotoxicity when compared with other local anaesthetics.
It has found uses also in the treatment of Arrhythmias eg: problems of the electrical system of the heart, causing it to pump less efficiently.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Lignocaine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Lignocaine.gif|200px{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <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>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
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="3" bgcolor="#ffffff" |
|-
| [[CA Index Name]]
| colspan="2"| Acetamide,
2-(diethylamino)-N-(2,6-dimethylphenyl)- (9CI)
|-
| [[Commercial Names]]
|colspan="2"| Xylocaine (Astra)
Emla (Astra)

Instillagel (Cliniflex)

Laryng-o-jet (IMS)
|-
| [[Chemical formula|Molecular formula]]
| colspan="2" | C<sub>14</sub>H<sub>22</sub>N<sub>2</sub>O
|-
| [[Molar mass]]
| colspan="2" |234.2 g/mol
|-
| [[CAS registry number|CAS number]]
| colspan="2" | 137-58-6
|-
| [[Appearance]]
| colspan="2" | colourless crystalline powder
|-
! {{chembox header}} colspan="3"| Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| colspan="2" | g/cm
|-
| [[Solubility]] in [[Water_(molecule)|water (ph=7)]]
| colspan="2" | Soluble (15 g/L)
|-
| [[Melting point]]
| colspan="2" | 159-160 °C
|-
| [[Boiling point]]
| colspan="2" | 68.5 °C
|-
| [[Acid dissociation constant|Acidity]] (p''Ka'') 
| colspan="2" | 7.8
|-
| [[Flash Point]]
| colspan="2" | 166.0±24.6 °C
|-
| [[Enthalpy of Vaporization]]
| colspan="2" | 59.55±3.0 kJ/mol
|-
! {{chembox header}} colspan="3"| Structure
|-
| [[Crystal structure]] 
| colspan="2"|
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| colspan="2" |? [[Debye|D]]
|-
| {{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>
|-
|}

==Synthesis==
[[Image:synthesisoflinocaine.gif|200px{{PAGENAME}}]]

==IR spectrum of lidocaine==
[[Image:vlirlidocaine.gif]]

Above: The IR spectrum of lidocaine

==Mass spectrum of lidocaine==

[[Image:vlmasslidocaine.gif]]

Above: The mass spectrum of lidocaine

==What does Lignocaine do?==
• Stabilises neuronal membrane, prevents the initiation and transmission of nerve impulses

• Antiarrhythmic effect by increasing the electrical stimulation threshold of the ventricle during diastole

• Depresses slow spontaneous depolarisation (ie decreases automaticity)

• Increases period of effective refractory period

• Potent suppressor of abnormal cardiac activity

• Blocks activated & inactivated sodium channels

• Suppresses activity of depolarised, arrhythmogenic tissues while minimally interfering with the electrical activity of normal tissues: therefore is effective in suppressing arrhythmias associated with depolarisation [eg ischaemia, digitalis toxicity] but is relatively ineffective against arrhythmias occurring in normally polarised cells [eg AF & Af]

• Lignocaine can act as a local anaesthetic by preventing sodium ions flowing through the nerve membrane, so this stops nerve impulses along nerve fibres ([http://www.medsafe.govt.nz/Profs/Datasheet/x/Xyloproctointsupp.htm]), without loss of consciousness.

[[Image:Vlanaesthetic.jpg|thumb|anaesthetic mechanism [http://www.frca.co.uk/article.aspx?articleid=100505])]]

The amide group (-CONH-) in Lignocaine allows it to act in the sodium channels of the nerve membrane.
When Lignocaine is applied on the skin, the compound is absorbed by the mucus membrane. The rate of absorption is dependent on the concentration of the dose. If Lignocaine is injected into the vein, it takes about 2 hours for half the amount of Lignocaine injected to metabolise.

The amide bond in lignocaine is more stronger than the ester linkage in drugs that contain ester links. So the amide type drugs such as lignocaine are more stable when dissolved in a solvent such as water, and can be stored for longer.
Lignocaine rarely causes allergic reactions in comparison to drugs which contains ester links. This is due to most of the ester type drugs causing the production of para-aminobenzoate (PABA) during metabolism, which causes the allergic reactions.

The natural pH of the human body is about 7.4, which causes most local anaesthetics to become more ionised than unionised. The pKa of Lignocaine is 7.9([http://www.frca.co.uk/article.aspx?articleid=100505]), which means that about 25% of the drug is unionised at pH 7.4. The Lignocaine must enter cells by passing the lipid membrane, which allows the unionised form of local anaesthetics to reach the target cells more quickly.

Lignocaine is metabolised in the liver by amidases, which hydrolyses the amide bond in Lignocaine. This process is slow, and so the drug can accumulate when further doses are taken by the patient. Lignocaine will act as an antiarrhythmic to stop irregular heart beat.

• In the US, patches containing lidocaine are marketed under the name LIDODERM®. These skin patches are used to relieve pain from Post-Herpetic Neralgia (the tingling pains also known as post-shingles pain). The adhesive patch contains 700mg of licocaine, which is enough to penetrate the skin to relieve the pain, but not enought to block the pain sensory receptors. The graph below, shows the average concentration of lidocaine in the blood of 15 normal, healthy volunteers:

[[Image:vlgraphlidocaine.gif]]

The graph shows that the concentration of lidocaine peaks at about the 12 hours mark, and then falls.
3 patches were applied at the same time for 3 consecutive days.
The concentrations of lidocaine in the blood, binds to mainly the plasma protein, alpha-1-acid glycoprotein.
At high plasma concentrations, lidocaine binds to the plasma protein concentration dependently.
Lidocaine can cross the placenta barrier and blood-brain barrier, by passive diffusion.

==Uses==

Lignocaine acts by provisionally blocking conduction over the nerve fibers.

When used in concentrations of 2-4% it produces a surface anaesthesia. Commonly injected at 1%, it has a rapid onset and a half life of about 90- 120 minutes.
It is commonly mixed with adrenaline in order to limit the bleeding, thus becoming a good face or scalp anaesthetic.

Lignocaine is also classified as a Class Ib antiarrhythmic agent.

==Contraindications==

Possible side effects:

• visual disturbances

• convulsions

• hypotension

• agitation

• deteriorating conscious level

• heart failure - negatively inotropic

• bradycardia - asystole

• left ventricular failure

An overdosage of lignocaine can result in convulsions, twitching and psychosis.

== Symptoms of allergic reaction to Lignocaine==

• Cough

• Difficulty swallowing or tongue swelling

• Dizziness or fainting; hives or swelling of eyelids, face or lips

• Itching or skin rash

• Stuffy nose

• Chest tightness

• Shortness of breath

• Troubled breathing or wheezing

== Signs of too much medicine being absorbed into the body ==
• Blurred or double vision

• Confusion

• Dizziness

• Light-headedness or drowsiness

• Feeling hot, cold, or numb

• Muscle twitching or trembling

• Nausea or vomiting

• Ringing or buzzing in the ears

• Shortness of breath or trouble breathing

• Unusual excitement

• Nervousness or restlessness

• Unusual tiredness or weakness

(The above side effects may occur if the medicine is used too often, applied to broken or inflamed skin, applied to very large areas, or kept on the skin too long.)

==References==
http://www.themediweb.net/pharmacy/Lignocaine.htm

http://www.elephantcare.org/Drugs/lidocain.htm

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=IR&Large=on

http://webbook.nist.gov/cgi/cbook.cgi?Spec=C137586&Index=0&Type=Mass&Large=on

http://www.perfusion.com.au/CCP/Pharmacology/lignocaine.htm

http://pharmacypractice.netfirms.com/kinetics/19/

http://www.healthtouch.com/bin/EContent_HT/drugShowLfts.asp?fname=usp0778.htm&title=Lignocaine&cid=HT

http://www.lidoderm.com/

http://www.medsafe.govt.nz/Profs/Datasheet/x/Xyloproctointsupp.htm

http://www.frca.co.uk/article.aspx?articleid=100505

File:Vlanaesthetic.jpg

2006-11-09T10:37:41Z

Vl105: anaesthetic mechanism

anaesthetic mechanism

It:Ferrocene

2006-10-27T11:21:01Z

Vl105: added mass spectrum of ferrocene

Ferrocene is an organomettalic compound of a type known as sandwich compounds. The name is because the central metal atom is bound between two cyclopentadienyl rings like the filling of a sandwich. The chemical formula of this compound is Fe(C5H5)2.

== Structure ==

[[Image:Ferrocene.jpg]]

<jmol>
<jmolApplet>
<size>400</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>102-54-5
WLViewer 3D 0

11 20 0 0 0 0 0 0 0 0999 V2000
8.7690 9.6516 -0.1910 Fe 0 2 0 0 0 0 0 0 0 1
9.4305 10.9070 0.9015 C 0 1 0 0 0 0 0 0 0 2
9.6682 11.2032 -0.8327 C 0 5 0 0 0 0 0 0 0 3
7.2426 10.7683 0.1163 C 0 0 0 0 0 0 0 0 0 4
7.8895 10.9970 -1.0578 C 0 0 0 0 0 0 0 0 0 5
9.5712 7.9079 -0.0581 C 0 0 0 0 0 0 0 0 0 6
8.7504 8.0104 -1.1574 C 0 0 0 0 0 0 0 0 0 7
7.6268 8.6166 0.8237 C 0 0 0 0 0 0 0 0 0 8
7.2628 8.5782 -0.9293 C 0 5 0 0 0 0 0 0 0 9
8.8478 8.2759 1.1499 C 0 0 0 0 0 0 0 0 0 10
8.1252 10.7293 1.2377 C 0 0 0 0 0 0 0 0 0 11
1 2 1 0 0 0
1 3 1 0 0 0
1 4 1 0 0 0
1 5 1 0 0 0
1 6 1 0 0 0
1 7 1 0 0 0
1 8 1 0 0 0
1 9 1 0 0 0
1 10 1 0 0 0
1 11 1 0 0 0
2 3 1 0 0 0
2 11 2 0 0 0
3 5 1 0 0 0
4 5 2 0 0 0
4 11 1 0 0 0
6 7 2 0 0 0
6 10 1 0 0 0
7 9 1 0 0 0
8 9 1 0 0 0
8 10 2 0 0 0
M END
</inlineContents>
</jmolApplet>
</jmol>

Above: 3D structure of ferrocene

Ferrocene is famous for its 'sandwich structure'. This is where the two cyclopentadiene molecules are situated above and below the iron centre, with the bonding occuring via the pi-electrons of the aromatic rings, which are shared with the central iron ion. This delocalised configuration of electrons is particularly stable. X-Ray diffraction in 1952 by Fisher showed that the cylopentadiene rings are staggered.

== History ==

Ernst Fischer and Geoffrey Wilkinson (Inorganic Chemist at Imperial College, London) were awarded the Nobel prize for Chemistry in 1974 for his work in determining the structure of ferrocene. This was for work done 20 years earlier starting in 1952(ref 2), after the compound had first been synthesised in December 1951 by T.J. Kealy and P.L. Pauson (ref 3).

== Data ==

{| border="1"
|+ '''Physical data for Ferrocene'''
|-
! Boiling Point
|249 °C (522 K)||
|-
! Melting point
|174 –176°C (447–449 K)||
|-
! Density
|1,490 g/m3 (20 °C)||
|-
! Formula Weight
|186.04 amu||
|}

=== IR Spectrum ===
[[Image:vlirspectrumferrocene.gif]]

Above: IR spectrum of ferrocene (ref 1)

=== Mass Spectrum ===
[[Image:vlmassspectrumferrocene.jpg]]

Above: mass spectrum of ferrocene (ref 4)

== Physical Properties ==

Ferrocene is an yellow-orange solid that stable in air. Ferrocene is soluble in organic solvents but is insoluble in water. Ferrocene will sublime in a vacuum

==References==

1. Data provided by the National Institute of Advanced Industrial Science and Technology (Japan)

2.Wilkinson and Woodward( J. Am. Chem. Soc. 1952, 74, 2125)

3. T.J. Kealy and P.L. Pauson (Nature, 15/12/51)

4. Spectral data provided by Wiley Subscription Services, Inc. (US)

--[[User:Jtm05|Jtm05]] 12:14, 27 October 2006 (BST)

--[[User:Vl105|Vl105]] 11:50, 27 October 2006 (BST)

File:Vlmassspectrumferrocene.jpg

2006-10-27T11:05:02Z

Vl105: mass spectrum of ferrocene

mass spectrum of ferrocene

It:Ferrocene

2006-10-27T11:02:23Z

Vl105:

Ferrocene is an organomettalic compound of a type known as sandwich compounds. The name is because the central metal atom is bound between two cyclopentadienyl rings like the filling of a sandwich. The chemical formula of this compound is Fe(C5H5)2.

== Structure ==

[[Image:Ferrocene.jpg]]

<jmol>
<jmolApplet>
<size>400</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>102-54-5
WLViewer 3D 0

11 20 0 0 0 0 0 0 0 0999 V2000
8.7690 9.6516 -0.1910 Fe 0 2 0 0 0 0 0 0 0 1
9.4305 10.9070 0.9015 C 0 1 0 0 0 0 0 0 0 2
9.6682 11.2032 -0.8327 C 0 5 0 0 0 0 0 0 0 3
7.2426 10.7683 0.1163 C 0 0 0 0 0 0 0 0 0 4
7.8895 10.9970 -1.0578 C 0 0 0 0 0 0 0 0 0 5
9.5712 7.9079 -0.0581 C 0 0 0 0 0 0 0 0 0 6
8.7504 8.0104 -1.1574 C 0 0 0 0 0 0 0 0 0 7
7.6268 8.6166 0.8237 C 0 0 0 0 0 0 0 0 0 8
7.2628 8.5782 -0.9293 C 0 5 0 0 0 0 0 0 0 9
8.8478 8.2759 1.1499 C 0 0 0 0 0 0 0 0 0 10
8.1252 10.7293 1.2377 C 0 0 0 0 0 0 0 0 0 11
1 2 1 0 0 0
1 3 1 0 0 0
1 4 1 0 0 0
1 5 1 0 0 0
1 6 1 0 0 0
1 7 1 0 0 0
1 8 1 0 0 0
1 9 1 0 0 0
1 10 1 0 0 0
1 11 1 0 0 0
2 3 1 0 0 0
2 11 2 0 0 0
3 5 1 0 0 0
4 5 2 0 0 0
4 11 1 0 0 0
6 7 2 0 0 0
6 10 1 0 0 0
7 9 1 0 0 0
8 9 1 0 0 0
8 10 2 0 0 0
M END
</inlineContents>
</jmolApplet>
</jmol>

Above: 3D structure of ferrocene

Ferrocene is famous for its 'sandwich structure'. This is where the two cyclopentadiene molecules are situated above and below the iron centre, with the bonding occuring via the pi-electrons of the aromatic rings, which are shared with the central iron ion. This delocalised configuration of electrons is particularly stable. X-Ray diffraction in 1952 by Fisher showed that the cylopentadiene rings are staggered.

== History ==

Ernst Fischer and Geoffrey Wilkinson (Inorganic Chemist at Imperial College, London) were awarded the Nobel prize for Chemistry in 1974 for his work in determining the structure of ferrocene. This was for work done 20 years earlier starting in 1952, after the compound had first been synthesised in December 1951 by T.J. Kealy and P.L. Pauson.

== Data ==

[[Image:vlirspectrumferrocene.gif]]

Above: IR spectrum of ferrocene (ref 1)

== Physical Properties ==

Ferrocene is an orange solid that stable in air. Ferrocene is soluble in organic solvents but is insoluble in water. Ferrocene will sublime in a vacuum

==References==

1. Data provided by the National Institute of Advanced Industrial Science and Technology (Japan)

--[[User:Jtm05|Jtm05]] 11:50, 27 October 2006 (BST)

--[[User:Vl105|Vl105]] 11:50, 27 October 2006 (BST)

It:Ferrocene

2006-10-27T10:59:22Z

Vl105: added ir spectrum of ferrocene

Ferrocene is an organomettalic compound of a type known as sandwich compounds. The name is because the central metal atom is bound between two cyclopentadienyl rings like the filling of a sandwich. The chemical formula of this compound is Fe(C5H5)2.

== Structure ==

[[Image:Ferrocene.jpg]]

<jmol>
<jmolApplet>
<size>400</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>102-54-5
WLViewer 3D 0

11 20 0 0 0 0 0 0 0 0999 V2000
8.7690 9.6516 -0.1910 Fe 0 2 0 0 0 0 0 0 0 1
9.4305 10.9070 0.9015 C 0 1 0 0 0 0 0 0 0 2
9.6682 11.2032 -0.8327 C 0 5 0 0 0 0 0 0 0 3
7.2426 10.7683 0.1163 C 0 0 0 0 0 0 0 0 0 4
7.8895 10.9970 -1.0578 C 0 0 0 0 0 0 0 0 0 5
9.5712 7.9079 -0.0581 C 0 0 0 0 0 0 0 0 0 6
8.7504 8.0104 -1.1574 C 0 0 0 0 0 0 0 0 0 7
7.6268 8.6166 0.8237 C 0 0 0 0 0 0 0 0 0 8
7.2628 8.5782 -0.9293 C 0 5 0 0 0 0 0 0 0 9
8.8478 8.2759 1.1499 C 0 0 0 0 0 0 0 0 0 10
8.1252 10.7293 1.2377 C 0 0 0 0 0 0 0 0 0 11
1 2 1 0 0 0
1 3 1 0 0 0
1 4 1 0 0 0
1 5 1 0 0 0
1 6 1 0 0 0
1 7 1 0 0 0
1 8 1 0 0 0
1 9 1 0 0 0
1 10 1 0 0 0
1 11 1 0 0 0
2 3 1 0 0 0
2 11 2 0 0 0
3 5 1 0 0 0
4 5 2 0 0 0
4 11 1 0 0 0
6 7 2 0 0 0
6 10 1 0 0 0
7 9 1 0 0 0
8 9 1 0 0 0
8 10 2 0 0 0
M END
</inlineContents>
</jmolApplet>
</jmol>

Above: 3D structure of ferrocene

Ferrocene is famous for its 'sandwich structure'. This is where the two cyclopentadiene molecules are situated above and below the iron centre, with the bonding occuring via the pi-electrons of the aromatic rings, which are shared with the central iron ion. This delocalised configuration of electrons is particularly stable. X-Ray diffraction in 1952 by Fisher showed that the cylopentadiene rings are staggered.

== History ==

Ernst Fischer and Geoffrey Wilkinson (Inorganic Chemist at Imperial College, London) were awarded the Nobel prize for Chemistry in 1974 for his work in determining the structure of ferrocene. This was for work done 20 years earlier starting in 1952, after the compound had first been synthesised in December 1951 by T.J. Kealy and P.L. Pauson.

== Data ==

[[Image:vlirspectrumferrocene.gif]]

== Physical Properties ==

Ferrocene is an orange solid that stable in air. Ferrocene is soluble in organic solvents but is insoluble in water. Ferrocene will sublime in a vacuum

--[[User:Jtm05|Jtm05]] 11:50, 27 October 2006 (BST)

--[[User:Vl105|Vl105]] 11:50, 27 October 2006 (BST)

File:Vlirspectrumferrocene.gif

2006-10-27T10:58:21Z

Vl105: ir spectrum of ferrocene

ir spectrum of ferrocene

It:Ferrocene

2006-10-27T10:57:43Z

Vl105:

Ferrocene is an organomettalic compound of a type known as sandwich compounds. The name is because the central metal atom is bound between two cyclopentadienyl rings like the filling of a sandwich. The chemical formula of this compound is Fe(C5H5)2.

== Structure ==

[[Image:Ferrocene.jpg]]

<jmol>
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<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>102-54-5
WLViewer 3D 0

11 20 0 0 0 0 0 0 0 0999 V2000
8.7690 9.6516 -0.1910 Fe 0 2 0 0 0 0 0 0 0 1
9.4305 10.9070 0.9015 C 0 1 0 0 0 0 0 0 0 2
9.6682 11.2032 -0.8327 C 0 5 0 0 0 0 0 0 0 3
7.2426 10.7683 0.1163 C 0 0 0 0 0 0 0 0 0 4
7.8895 10.9970 -1.0578 C 0 0 0 0 0 0 0 0 0 5
9.5712 7.9079 -0.0581 C 0 0 0 0 0 0 0 0 0 6
8.7504 8.0104 -1.1574 C 0 0 0 0 0 0 0 0 0 7
7.6268 8.6166 0.8237 C 0 0 0 0 0 0 0 0 0 8
7.2628 8.5782 -0.9293 C 0 5 0 0 0 0 0 0 0 9
8.8478 8.2759 1.1499 C 0 0 0 0 0 0 0 0 0 10
8.1252 10.7293 1.2377 C 0 0 0 0 0 0 0 0 0 11
1 2 1 0 0 0
1 3 1 0 0 0
1 4 1 0 0 0
1 5 1 0 0 0
1 6 1 0 0 0
1 7 1 0 0 0
1 8 1 0 0 0
1 9 1 0 0 0
1 10 1 0 0 0
1 11 1 0 0 0
2 3 1 0 0 0
2 11 2 0 0 0
3 5 1 0 0 0
4 5 2 0 0 0
4 11 1 0 0 0
6 7 2 0 0 0
6 10 1 0 0 0
7 9 1 0 0 0
8 9 1 0 0 0
8 10 2 0 0 0
M END
</inlineContents>
</jmolApplet>
</jmol>

Above: 3D structure of ferrocene

Ferrocene is famous for its 'sandwich structure'. This is where the two cyclopentadiene molecules are situated above and below the iron centre, with the bonding occuring via the pi-electrons of the aromatic rings, which are shared with the central iron ion. This delocalised configuration of electrons is particularly stable. X-Ray diffraction in 1952 by Fisher showed that the cylopentadiene rings are staggered.

== History ==

Ernst Fischer and Geoffrey Wilkinson (Inorganic Chemist at Imperial College, London) were awarded the Nobel prize for Chemistry in 1974 for his work in determining the structure of ferrocene. This was for work done 20 years earlier starting in 1952, after the compound had first been synthesised in December 1951 by T.J. Kealy and P.L. Pauson.

--[[User:Jtm05|Jtm05]] 11:50, 27 October 2006 (BST)

--[[User:Vl105|Vl105]] 11:50, 27 October 2006 (BST)

It:Ferrocene

2006-10-27T10:57:20Z

Vl105: added caption to 3D structure

Ferrocene is an organomettalic compound of a type known as sandwich compounds. The name is because the central metal atom is bound between two cyclopentadienyl rings like the filling of a sandwich. The chemical formula of this compound is Fe(C5H5)2.

== Structure ==

[[Image:Ferrocene.jpg]]

<jmol>
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WLViewer 3D 0

11 20 0 0 0 0 0 0 0 0999 V2000
8.7690 9.6516 -0.1910 Fe 0 2 0 0 0 0 0 0 0 1
9.4305 10.9070 0.9015 C 0 1 0 0 0 0 0 0 0 2
9.6682 11.2032 -0.8327 C 0 5 0 0 0 0 0 0 0 3
7.2426 10.7683 0.1163 C 0 0 0 0 0 0 0 0 0 4
7.8895 10.9970 -1.0578 C 0 0 0 0 0 0 0 0 0 5
9.5712 7.9079 -0.0581 C 0 0 0 0 0 0 0 0 0 6
8.7504 8.0104 -1.1574 C 0 0 0 0 0 0 0 0 0 7
7.6268 8.6166 0.8237 C 0 0 0 0 0 0 0 0 0 8
7.2628 8.5782 -0.9293 C 0 5 0 0 0 0 0 0 0 9
8.8478 8.2759 1.1499 C 0 0 0 0 0 0 0 0 0 10
8.1252 10.7293 1.2377 C 0 0 0 0 0 0 0 0 0 11
1 2 1 0 0 0
1 3 1 0 0 0
1 4 1 0 0 0
1 5 1 0 0 0
1 6 1 0 0 0
1 7 1 0 0 0
1 8 1 0 0 0
1 9 1 0 0 0
1 10 1 0 0 0
1 11 1 0 0 0
2 3 1 0 0 0
2 11 2 0 0 0
3 5 1 0 0 0
4 5 2 0 0 0
4 11 1 0 0 0
6 7 2 0 0 0
6 10 1 0 0 0
7 9 1 0 0 0
8 9 1 0 0 0
8 10 2 0 0 0
M END
</inlineContents>
</jmolApplet>
</jmol>

Above: 3D structure of ferrocene

Ferrocene is famous for its 'sandwich structure'. This is where the two cyclopentadiene molecules are situated above and below the iron centre, with the bonding occuring via the pi-electrons of the aromatic rings, which are shared with the central iron ion. This delocalised configuration of electrons is particularly stable. X-Ray diffraction in 1952 by Fisher showed that the cylopentadiene rings are staggered.

== History ==

Ernst Fischer and Geoffrey Wilkinson (Inorganic Chemist at Imperial College, London) were awarded the Nobel prize for Chemistry in 1974 for his work in determining the structure of ferrocene. This was for work done 20 years earlier starting in 1952, after the compound had first been synthesised in December 1951 by T.J. Kealy and P.L. Pauson.

--[[User:Jtm05|Jtm05]] 11:50, 27 October 2006 (BST)

--[[User:Vl105|Vl105]] 11:50, 27 October 2006 (BST)

It:Ferrocene

2006-10-27T10:50:51Z

Vl105:

It:Ferrocene

2006-10-27T10:47:43Z

Vl105: added 3d structure of ferrocene with black background

It:Ferrocene

2006-10-27T10:44:22Z

Vl105:

File:Vlmassspectrumofgingerone.GIF

2006-10-26T16:29:46Z

Vl105: mass spectrum of gingerone

mass spectrum of gingerone

It:Gingerone

2006-10-26T16:24:50Z

Vl105: added text to 3d structure of gingerol

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D Structure of Zingerone
|-
| align="center" colspan="3" bgcolour="#ffffff" | [[Image:Untitled.gif]]
|-
! {{chembox header}} colspan="3" |3D structure of Zingerone <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>
HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 O 0 3.909 -1.039 -0.489 0.00 0.00 O+0
ATOM 2 C 0 2.599 -0.845 -0.181 0.00 0.00 C+0
ATOM 3 C 0 2.106 0.445 -0.009 0.00 0.00 C+0
ATOM 4 O 0 2.934 1.515 -0.149 0.00 0.00 O+0
ATOM 5 C 0 2.143 2.682 0.086 0.00 0.00 C+0
ATOM 6 C 0 0.770 0.636 0.305 0.00 0.00 C+0
ATOM 7 C 0 -0.070 -0.452 0.446 0.00 0.00 C+0
ATOM 8 C 0 -1.523 -0.242 0.787 0.00 0.00 C+0
ATOM 9 C 0 -2.335 -0.105 -0.502 0.00 0.00 C+0
ATOM 10 C 0 -3.788 0.105 -0.161 0.00 0.00 C+0
ATOM 11 C 0 -4.804 0.269 -1.261 0.00 0.00 C+0
ATOM 12 O 0 -4.137 0.142 0.995 0.00 0.00 O+0
ATOM 13 C 0 0.419 -1.734 0.275 0.00 0.00 C+0
ATOM 14 C 0 1.750 -1.932 -0.044 0.00 0.00 C+0
ATOM 15 H 0 4.384 -1.120 0.349 0.00 0.00 H+0
ATOM 16 H 0 1.331 2.723 -0.641 0.00 0.00 H+0
ATOM 17 H 0 1.728 2.643 1.093 0.00 0.00 H+0
ATOM 18 H 0 2.767 3.570 -0.016 0.00 0.00 H+0
ATOM 19 H 0 0.385 1.637 0.439 0.00 0.00 H+0
ATOM 20 H 0 -1.889 -1.094 1.359 0.00 0.00 H+0
ATOM 21 H 0 -1.629 0.666 1.381 0.00 0.00 H+0
ATOM 22 H 0 -1.969 0.747 -1.074 0.00 0.00 H+0
ATOM 23 H 0 -2.229 -1.013 -1.096 0.00 0.00 H+0
ATOM 24 H 0 -4.306 0.208 -2.228 0.00 0.00 H+0
ATOM 25 H 0 -5.551 -0.521 -1.186 0.00 0.00 H+0
ATOM 26 H 0 -5.291 1.240 -1.164 0.00 0.00 H+0
ATOM 27 H 0 -0.240 -2.582 0.386 0.00 0.00 H+0
ATOM 28 H 0 2.130 -2.934 -0.178 0.00 0.00 H+0
CONECT 1 2 15 0 0 NONE 33
CONECT 2 1 14 3 0 NONE 34
CONECT 3 2 4 6 0 NONE 35
CONECT 4 3 5 0 0 NONE 36
CONECT 5 4 16 17 18 NONE 37
CONECT 6 3 7 19 0 NONE 38
CONECT 7 6 8 13 0 NONE 39
CONECT 8 7 9 20 21 NONE 40
CONECT 9 8 10 22 23 NONE 41
CONECT 10 9 11 12 0 NONE 42
CONECT 11 10 24 25 26 NONE 43
CONECT 12 10 0 0 0 NONE 44
CONECT 13 7 14 27 0 NONE 45
CONECT 14 13 2 28 0 NONE 46
END NONE 47
</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | Properties
|-
| colspan="1" |IUPAC Systematic Name
| colspan="2"|4-(4-hydroxy-3-methoxyphenyl)-2-butanone
|-
| colspan="1" |Molecular formula
| colspan="2" |C<sub>11</sub>H<sub>14</sub>O<sub>3</sub>
|-
| colspan="1" |SMILES String
| colspan="2" |OC1=C(OC)C=C(CCC(C)=O)C=C1
|-
| colspan="1" |Molecular Mass
| colspan="2" |194 g/mol
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |2051099
|-
| colspan="1" |CAS Registry Number
| colspan="2" |122-48-5
|-
| Melting Point
| colspan="2" |40-42°C

|}

==Zingerone== is the molecule responsible for most of the taste of cooked ginger. It is also a week antioxidant, and this may account for some of the proposed medicinal properties of the compound.

Many other molecules which give foods taste and smell are chemically similar to zingerone, most notably capsaicin and vanillin, which give vanilla and hot peppers their tastes. Zingerone has a higher molecular weight than vanillin, and contains a carbonyl side group which allows stronger Van Der Waals interactions. This means zingerone can bind strongly to itself when compared with molecules like vanillin. This in turn makes zingerone less volatile, which accounts for the fact that while vanilla and ginger give similarly strong tastes, vanilla's smell is much more potent. It can escape more readily as a gas. On the other hand, capsaicin is a heavier molecule than zingerone, is much less volatile, and therefore is completely odourless.
To compare zingerone with several other 'taste' molecules see [http://antoine.frostburg.edu/chem/senese/101/features/capsaicin.shtml General Chemistry Online: Fire and Spice]

Fresh ginger contains no zingerone. When ginger is cooked gingerol, a molecule present in fresh ginger, reacts to give zingerone. Whereas gingerol has an extremely strong taste, zingerone has a milder, sweeter taste.

[[Image:gingerol.gif|50px]]
Chemical structure of gingerol, a precursor of gingerone

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 O 0 5.987 -0.884 -0.823 0.00 0.00 O+0
ATOM 2 C 0 4.709 -0.762 -0.373 0.00 0.00 C+0
ATOM 3 C 0 4.152 0.500 -0.190 0.00 0.00 C+0
ATOM 4 O 0 4.884 1.614 -0.459 0.00 0.00 O+0
ATOM 5 C 0 4.047 2.737 -0.176 0.00 0.00 C+0
ATOM 6 C 0 2.850 0.619 0.269 0.00 0.00 C+0
ATOM 7 C 0 2.107 -0.514 0.542 0.00 0.00 C+0
ATOM 8 C 0 0.691 -0.382 1.040 0.00 0.00 C+0
ATOM 9 C 0 -0.268 -0.352 -0.152 0.00 0.00 C+0
ATOM 10 C 0 -1.685 -0.220 0.347 0.00 0.00 C+0
ATOM 11 C 0 -2.827 -0.167 -0.635 0.00 0.00 C+0
ATOM 12 C 0 -4.147 -0.033 0.126 0.00 0.00 C+0
ATOM 13 O 0 -4.178 1.221 0.810 0.00 0.00 O+0
ATOM 14 C 0 -5.314 -0.104 -0.861 0.00 0.00 C+0
ATOM 15 C 0 -6.636 -0.096 -0.090 0.00 0.00 C+0
ATOM 16 C 0 -7.803 -0.167 -1.077 0.00 0.00 C+0
ATOM 17 O 0 -1.904 -0.158 1.532 0.00 0.00 O+0
ATOM 18 C 0 2.660 -1.768 0.359 0.00 0.00 C+0
ATOM 19 C 0 3.957 -1.893 -0.103 0.00 0.00 C+0
ATOM 20 H 0 6.557 -0.900 -0.042 0.00 0.00 H+0
ATOM 21 H 0 3.751 2.714 0.873 0.00 0.00 H+0
ATOM 22 H 0 4.594 3.658 -0.378 0.00 0.00 H+0
ATOM 23 H 0 3.158 2.696 -0.805 0.00 0.00 H+0
ATOM 24 H 0 2.415 1.598 0.412 0.00 0.00 H+0
ATOM 25 H 0 0.450 -1.232 1.679 0.00 0.00 H+0
ATOM 26 H 0 0.591 0.541 1.611 0.00 0.00 H+0
ATOM 27 H 0 -0.027 0.498 -0.790 0.00 0.00 H+0
ATOM 28 H 0 -0.168 -1.275 -0.722 0.00 0.00 H+0
ATOM 29 H 0 -2.699 0.691 -1.295 0.00 0.00 H+0
ATOM 30 H 0 -2.840 -1.082 -1.227 0.00 0.00 H+0
ATOM 31 H 0 -4.234 -0.844 0.849 0.00 0.00 H+0
ATOM 32 H 0 -4.099 1.910 0.135 0.00 0.00 H+0
ATOM 33 H 0 -5.278 0.756 -1.529 0.00 0.00 H+0
ATOM 34 H 0 -5.240 -1.021 -1.446 0.00 0.00 H+0
ATOM 35 H 0 -6.672 -0.956 0.578 0.00 0.00 H+0
ATOM 36 H 0 -6.710 0.821 0.494 0.00 0.00 H+0
ATOM 37 H 0 -8.744 -0.161 -0.528 0.00 0.00 H+0
ATOM 38 H 0 -7.766 0.694 -1.746 0.00 0.00 H+0
ATOM 39 H 0 -7.729 -1.084 -1.662 0.00 0.00 H+0
ATOM 40 H 0 2.076 -2.651 0.573 0.00 0.00 H+0
ATOM 41 H 0 4.387 -2.874 -0.245 0.00 0.00 H+0
CONECT 1 2 20 0 0 NONE 46
CONECT 2 1 19 3 0 NONE 47
CONECT 3 2 4 6 0 NONE 48
CONECT 4 3 5 0 0 NONE 49
CONECT 5 4 21 22 23 NONE 50
CONECT 6 3 7 24 0 NONE 51
CONECT 7 6 8 18 0 NONE 52
CONECT 8 7 9 25 26 NONE 53
CONECT 9 8 10 27 28 NONE 54
CONECT 10 9 11 17 0 NONE 55
CONECT 11 10 12 29 30 NONE 56
CONECT 12 11 13 14 31 NONE 57
CONECT 13 12 32 0 0 NONE 58
CONECT 14 12 15 33 34 NONE 59
CONECT 15 14 16 35 36 NONE 60
CONECT 16 15 37 38 39 NONE 61
CONECT 17 10 0 0 0 NONE 62
CONECT 18 7 19 40 0 NONE 63
CONECT 19 18 2 41 0 NONE 64
END NONE 65
</inlineContents>
</jmolApplet>
</jmol>

Above: 3D strutcture of [4]-Gingerol

There is some evidence that gingerol has therapeutic properties that help with symptoms like nausea and vomiting, and may be of some use as a natural remedy to things like morning sickness and seasickness. There is some controversy as to these effects because not all studies show any effect when compared with a placebo.
[http://bja.oxfordjournals.org/cgi/content/abstract/84/3/367 Article:efficacy of ginger for nausea and vomiting]

==Zingerone synthesis==

[[Image:Zingerone synthesis.gif|thumb|Description]]

In 1968 CONNELL and SUTHERLAND examined the structures and synthesis of zingerone. They found that it was possible to synthesise zingerone by hydrolysing gingerol using hot aqueous barium hydroxide solution. Other aldehydes are also produced in this reaction.

[[Image:Gingerol hydrolysis.gif|thumb|Description]]

{|-
! {{chembox header}} colspan="3" | Properties of Gingerol
|-
| colspan="1" |CAS Registry Number
| colspan="2"|41743-68-4, 77398-90-4
|-
| colspan="1" |Chemical Name
| colspan="2" |[4]-Gingerol
|-
| colspan="1" |Autoname
| colspan="2" |5-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-octan-3-one
|-
| colspan="1" |Molecular Formula
| colspan="2" |C15H22O4
|-
| colspan="1" |Molecular Weight
| colspan="2" |266.34
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |2051099
|-
| Melting Point
| colspan="2" |74-75°C

|}

==Spectra of Zingerone==

''Infrared Spectrum'':
[[Image:irzingerone.PNG]]

''Infra Red Assignements for Zingerone:''

C = O - 1700 cm<sup>-1</sup>

O - H - 3410 cm<sup>-1</sup>

''Mass Spectrum'':
[[Image:Zingerone.jpg|thumb|Description]]

==Uses of Zingerone by Chemical Scientists==
In 2005 an article in the American Chemical Society found that Zingerone inhibited the formation of peroxynitrite (ONOO<sup>-</sup> ), which is formed when a O2<sup>-</sup> radical reacts with an NO radical. This can cause strokes, atherosclerosis and even Alzheimer's disease. It was found that Zingerone aided with electron donation and so helping with the cells defense against many diseases.

==References==
* Spectra obtained from NIST Chemistry Web book - [http://webbook.nist.gov/chemistry/]
* Connell, D. W.; Sutherland, M. D. A Re-Examination of Gingerol, Shogaol, and Zingerone, The Pungent Principles of Ginger (Zingiber Officinule Roscoe). Aust. J. Chem. 1969,22, 1033-1043, and references cited therein.
* Properties of Gingerol was obtained from Beilstein (Beilstein registry number 1991143).
*Sang-Guk Shin, Ji Young Kim, et. al.; "Zingerone as an Antioxidant against Peroxynitrite"; American Chemical Society; August 2005

[[Further Abstract & Syntheses]]

It:Gingerone

2006-10-26T16:20:46Z

Vl105: /* Zingerone */

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |2D Structure of Zingerone
|-
| align="center" colspan="3" bgcolour="#ffffff" | [[Image:Untitled.gif]]
|-
! {{chembox header}} colspan="3" |3D structure of Zingerone <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>
HEADER NONAME 20-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 20-Oct-06 0 NONE 4
ATOM 1 O 0 3.909 -1.039 -0.489 0.00 0.00 O+0
ATOM 2 C 0 2.599 -0.845 -0.181 0.00 0.00 C+0
ATOM 3 C 0 2.106 0.445 -0.009 0.00 0.00 C+0
ATOM 4 O 0 2.934 1.515 -0.149 0.00 0.00 O+0
ATOM 5 C 0 2.143 2.682 0.086 0.00 0.00 C+0
ATOM 6 C 0 0.770 0.636 0.305 0.00 0.00 C+0
ATOM 7 C 0 -0.070 -0.452 0.446 0.00 0.00 C+0
ATOM 8 C 0 -1.523 -0.242 0.787 0.00 0.00 C+0
ATOM 9 C 0 -2.335 -0.105 -0.502 0.00 0.00 C+0
ATOM 10 C 0 -3.788 0.105 -0.161 0.00 0.00 C+0
ATOM 11 C 0 -4.804 0.269 -1.261 0.00 0.00 C+0
ATOM 12 O 0 -4.137 0.142 0.995 0.00 0.00 O+0
ATOM 13 C 0 0.419 -1.734 0.275 0.00 0.00 C+0
ATOM 14 C 0 1.750 -1.932 -0.044 0.00 0.00 C+0
ATOM 15 H 0 4.384 -1.120 0.349 0.00 0.00 H+0
ATOM 16 H 0 1.331 2.723 -0.641 0.00 0.00 H+0
ATOM 17 H 0 1.728 2.643 1.093 0.00 0.00 H+0
ATOM 18 H 0 2.767 3.570 -0.016 0.00 0.00 H+0
ATOM 19 H 0 0.385 1.637 0.439 0.00 0.00 H+0
ATOM 20 H 0 -1.889 -1.094 1.359 0.00 0.00 H+0
ATOM 21 H 0 -1.629 0.666 1.381 0.00 0.00 H+0
ATOM 22 H 0 -1.969 0.747 -1.074 0.00 0.00 H+0
ATOM 23 H 0 -2.229 -1.013 -1.096 0.00 0.00 H+0
ATOM 24 H 0 -4.306 0.208 -2.228 0.00 0.00 H+0
ATOM 25 H 0 -5.551 -0.521 -1.186 0.00 0.00 H+0
ATOM 26 H 0 -5.291 1.240 -1.164 0.00 0.00 H+0
ATOM 27 H 0 -0.240 -2.582 0.386 0.00 0.00 H+0
ATOM 28 H 0 2.130 -2.934 -0.178 0.00 0.00 H+0
CONECT 1 2 15 0 0 NONE 33
CONECT 2 1 14 3 0 NONE 34
CONECT 3 2 4 6 0 NONE 35
CONECT 4 3 5 0 0 NONE 36
CONECT 5 4 16 17 18 NONE 37
CONECT 6 3 7 19 0 NONE 38
CONECT 7 6 8 13 0 NONE 39
CONECT 8 7 9 20 21 NONE 40
CONECT 9 8 10 22 23 NONE 41
CONECT 10 9 11 12 0 NONE 42
CONECT 11 10 24 25 26 NONE 43
CONECT 12 10 0 0 0 NONE 44
CONECT 13 7 14 27 0 NONE 45
CONECT 14 13 2 28 0 NONE 46
END NONE 47
</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | Properties
|-
| colspan="1" |IUPAC Systematic Name
| colspan="2"|4-(4-hydroxy-3-methoxyphenyl)-2-butanone
|-
| colspan="1" |Molecular formula
| colspan="2" |C<sub>11</sub>H<sub>14</sub>O<sub>3</sub>
|-
| colspan="1" |SMILES String
| colspan="2" |OC1=C(OC)C=C(CCC(C)=O)C=C1
|-
| colspan="1" |Molecular Mass
| colspan="2" |194 g/mol
|-
| colspan="1" |Appearance
| colspan="2" |
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |2051099
|-
| colspan="1" |CAS Registry Number
| colspan="2" |122-48-5
|-
| Melting Point
| colspan="2" |40-42°C

|}

==Zingerone== is the molecule responsible for most of the taste of cooked ginger. It is also a week antioxidant, and this may account for some of the proposed medicinal properties of the compound.

Many other molecules which give foods taste and smell are chemically similar to zingerone, most notably capsaicin and vanillin, which give vanilla and hot peppers their tastes. Zingerone has a higher molecular weight than vanillin, and contains a carbonyl side group which allows stronger Van Der Waals interactions. This means zingerone can bind strongly to itself when compared with molecules like vanillin. This in turn makes zingerone less volatile, which accounts for the fact that while vanilla and ginger give similarly strong tastes, vanilla's smell is much more potent. It can escape more readily as a gas. On the other hand, capsaicin is a heavier molecule than zingerone, is much less volatile, and therefore is completely odourless.
To compare zingerone with several other 'taste' molecules see [http://antoine.frostburg.edu/chem/senese/101/features/capsaicin.shtml General Chemistry Online: Fire and Spice]

Fresh ginger contains no zingerone. When ginger is cooked gingerol, a molecule present in fresh ginger, reacts to give zingerone. Whereas gingerol has an extremely strong taste, zingerone has a milder, sweeter taste.

[[Image:gingerol.gif|50px]]
Chemical structure of gingerol, a precursor of gingerone

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 O 0 5.987 -0.884 -0.823 0.00 0.00 O+0
ATOM 2 C 0 4.709 -0.762 -0.373 0.00 0.00 C+0
ATOM 3 C 0 4.152 0.500 -0.190 0.00 0.00 C+0
ATOM 4 O 0 4.884 1.614 -0.459 0.00 0.00 O+0
ATOM 5 C 0 4.047 2.737 -0.176 0.00 0.00 C+0
ATOM 6 C 0 2.850 0.619 0.269 0.00 0.00 C+0
ATOM 7 C 0 2.107 -0.514 0.542 0.00 0.00 C+0
ATOM 8 C 0 0.691 -0.382 1.040 0.00 0.00 C+0
ATOM 9 C 0 -0.268 -0.352 -0.152 0.00 0.00 C+0
ATOM 10 C 0 -1.685 -0.220 0.347 0.00 0.00 C+0
ATOM 11 C 0 -2.827 -0.167 -0.635 0.00 0.00 C+0
ATOM 12 C 0 -4.147 -0.033 0.126 0.00 0.00 C+0
ATOM 13 O 0 -4.178 1.221 0.810 0.00 0.00 O+0
ATOM 14 C 0 -5.314 -0.104 -0.861 0.00 0.00 C+0
ATOM 15 C 0 -6.636 -0.096 -0.090 0.00 0.00 C+0
ATOM 16 C 0 -7.803 -0.167 -1.077 0.00 0.00 C+0
ATOM 17 O 0 -1.904 -0.158 1.532 0.00 0.00 O+0
ATOM 18 C 0 2.660 -1.768 0.359 0.00 0.00 C+0
ATOM 19 C 0 3.957 -1.893 -0.103 0.00 0.00 C+0
ATOM 20 H 0 6.557 -0.900 -0.042 0.00 0.00 H+0
ATOM 21 H 0 3.751 2.714 0.873 0.00 0.00 H+0
ATOM 22 H 0 4.594 3.658 -0.378 0.00 0.00 H+0
ATOM 23 H 0 3.158 2.696 -0.805 0.00 0.00 H+0
ATOM 24 H 0 2.415 1.598 0.412 0.00 0.00 H+0
ATOM 25 H 0 0.450 -1.232 1.679 0.00 0.00 H+0
ATOM 26 H 0 0.591 0.541 1.611 0.00 0.00 H+0
ATOM 27 H 0 -0.027 0.498 -0.790 0.00 0.00 H+0
ATOM 28 H 0 -0.168 -1.275 -0.722 0.00 0.00 H+0
ATOM 29 H 0 -2.699 0.691 -1.295 0.00 0.00 H+0
ATOM 30 H 0 -2.840 -1.082 -1.227 0.00 0.00 H+0
ATOM 31 H 0 -4.234 -0.844 0.849 0.00 0.00 H+0
ATOM 32 H 0 -4.099 1.910 0.135 0.00 0.00 H+0
ATOM 33 H 0 -5.278 0.756 -1.529 0.00 0.00 H+0
ATOM 34 H 0 -5.240 -1.021 -1.446 0.00 0.00 H+0
ATOM 35 H 0 -6.672 -0.956 0.578 0.00 0.00 H+0
ATOM 36 H 0 -6.710 0.821 0.494 0.00 0.00 H+0
ATOM 37 H 0 -8.744 -0.161 -0.528 0.00 0.00 H+0
ATOM 38 H 0 -7.766 0.694 -1.746 0.00 0.00 H+0
ATOM 39 H 0 -7.729 -1.084 -1.662 0.00 0.00 H+0
ATOM 40 H 0 2.076 -2.651 0.573 0.00 0.00 H+0
ATOM 41 H 0 4.387 -2.874 -0.245 0.00 0.00 H+0
CONECT 1 2 20 0 0 NONE 46
CONECT 2 1 19 3 0 NONE 47
CONECT 3 2 4 6 0 NONE 48
CONECT 4 3 5 0 0 NONE 49
CONECT 5 4 21 22 23 NONE 50
CONECT 6 3 7 24 0 NONE 51
CONECT 7 6 8 18 0 NONE 52
CONECT 8 7 9 25 26 NONE 53
CONECT 9 8 10 27 28 NONE 54
CONECT 10 9 11 17 0 NONE 55
CONECT 11 10 12 29 30 NONE 56
CONECT 12 11 13 14 31 NONE 57
CONECT 13 12 32 0 0 NONE 58
CONECT 14 12 15 33 34 NONE 59
CONECT 15 14 16 35 36 NONE 60
CONECT 16 15 37 38 39 NONE 61
CONECT 17 10 0 0 0 NONE 62
CONECT 18 7 19 40 0 NONE 63
CONECT 19 18 2 41 0 NONE 64
END NONE 65
</inlineContents>
</jmolApplet>
</jmol>

There is some evidence that gingerol has therapeutic properties that help with symptoms like nausea and vomiting, and may be of some use as a natural remedy to things like morning sickness and seasickness. There is some controversy as to these effects because not all studies show any effect when compared with a placebo.
[http://bja.oxfordjournals.org/cgi/content/abstract/84/3/367 Article:efficacy of ginger for nausea and vomiting]

==Zingerone synthesis==

[[Image:Zingerone synthesis.gif|thumb|Description]]

In 1968 CONNELL and SUTHERLAND examined the structures and synthesis of zingerone. They found that it was possible to synthesise zingerone by hydrolysing gingerol using hot aqueous barium hydroxide solution. Other aldehydes are also produced in this reaction.

[[Image:Gingerol hydrolysis.gif|thumb|Description]]

{|-
! {{chembox header}} colspan="3" | Properties of Gingerol
|-
| colspan="1" |CAS Registry Number
| colspan="2"|41743-68-4, 77398-90-4
|-
| colspan="1" |Chemical Name
| colspan="2" |[4]-Gingerol
|-
| colspan="1" |Autoname
| colspan="2" |5-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-octan-3-one
|-
| colspan="1" |Molecular Formula
| colspan="2" |C15H22O4
|-
| colspan="1" |Molecular Weight
| colspan="2" |266.34
|-
|colspan="1" |Beilstein Registry number
| colspan="2" |2051099
|-
| Melting Point
| colspan="2" |74-75°C

|}

==Spectra of Zingerone==

''Infrared Spectrum'':
[[Image:irzingerone.PNG]]

''Infra Red Assignements for Zingerone:''

C = O - 1700 cm<sup>-1</sup>

O - H - 3410 cm<sup>-1</sup>

''Mass Spectrum'':
[[Image:Zingerone.jpg|thumb|Description]]

==Uses of Zingerone by Chemical Scientists==
In 2005 an article in the American Chemical Society found that Zingerone inhibited the formation of peroxynitrite (ONOO<sup>-</sup> ), which is formed when a O2<sup>-</sup> radical reacts with an NO radical. This can cause strokes, atherosclerosis and even Alzheimer's disease. It was found that Zingerone aided with electron donation and so helping with the cells defense against many diseases.

==References==
* Spectra obtained from NIST Chemistry Web book - [http://webbook.nist.gov/chemistry/]
* Connell, D. W.; Sutherland, M. D. A Re-Examination of Gingerol, Shogaol, and Zingerone, The Pungent Principles of Ginger (Zingiber Officinule Roscoe). Aust. J. Chem. 1969,22, 1033-1043, and references cited therein.
* Properties of Gingerol was obtained from Beilstein (Beilstein registry number 1991143).
*Sang-Guk Shin, Ji Young Kim, et. al.; "Zingerone as an Antioxidant against Peroxynitrite"; American Chemical Society; August 2005

[[Further Abstract & Syntheses]]

It:Hycocine

2006-10-26T15:59:59Z

Vl105: /* History of Hycocine */

== '''HYOSCINE''' ==

{| 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 that 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>
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<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 it 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. They studied the accumulation of scopolamine in cell and tissue cultures of Datura as a way of seeing on a biochemical level how the natural products scopolamine and hyoscyamine accumulate in plants of the Datura family. (Ref 2)

[[Image:Datura.jpg|thumb|''Datura wrightii'' ]] ''Datura wrightii''

Scopolamine can be isolated from plants by extraction:

[[Image:Biosynthesis_of_alkaloids2.GIF]] [http://www.plantcell.org/cgi/reprint/7/7/1059.pdf]

==Physical properties of Hycocine==

{| border="1"

|-
! Formula
| C1<sub>7</sub>H<sub>21</sub>NO<sub>4</sub>
|-
! Molecular weight
| 303.35
|-
! Melting point
| 59<sup>o</sup>C
|-
! Appearance
| white, amophous, semi-solid
|}

==Chemical Properties of Hycocine==

It is a drug that acts on the autonomic nervous system and prevents muscle spasm.
It is an alkaloid, obtained from various plants of the nightshade family (such as belladonna). [http://www.tiscali.co.uk/reference/encyclopaedia/hutchinson/m0014386.html]

The depressive action hycocine on the central nervous system makes it suitable for use in very tiny amounts in the treatment of
anxiety-related problems and travel-sickness (in the form of hyoscine hydrobromide, which is a type of anticholinergic drug).

In larger doses, it breaks down a person’s ability to discriminate and make reasoned judgment, making it a potential 'truth drug'.

==Effects of Hycocine==

It is frequently included in premedication to dry up lung secretions and as a postoperative sedative. It is also used to
treat ulcers, to relax the womb in labour, for travel sickness, and to dilate the pupils before an eye examination.

Hyoscine produces sedation. With higher doses it produces agitation and disorientation similar to that of atropine. Hyoscine also has a significant anti-emetic effect, and that is why it is used for the treatment of motion sickness (Rang et al., 1995)

Hyoscine induced a moderate bradycardia and a marked decrease in salivation when administered via injection. These
effects were maximal at 1 to 2 hours after administration of hyoscine but were no longer present at 4 hours.

Consistent behavioral effects of hyoscine in various experiments were a decrease in spontaneous speech and movement and a significant
decrease in energy.

When administered medically, hyoscine may cause the muscles in the eye to become relaxed, widening the pupil. Pupils may remain wide and not respond to light. They'll also be more sensitive.

Fatal doses of hyoscine causes the heart to cease functioning, which results in death.

There are side effects that are known to have affected patients (ref 6). The drug Hyoscine affects the autonomic nervous system so this could be the cause of those side effects:

* Dizziness
* Blurred vision
* Dry mouth
* Vomiting
* Irritation of the skin
* Problems in urinating

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''(+)-scopolamine'''
|-
! CAS Registry Number
| 51-34-3, 138-12-5, 64069-63-2, 124917-17-5
|-
! Chemical Name
|3-hydroxy-2-phenyl-propionic acid 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yl ester
|-
! Molecular Formula
| C17H21NO4
|-
! Molecular Weight
| 303.36
|-
|}

==Synthesis==

In 1957 Fodor synthesised scopolamine via 2 steps. He found that the first work up step to produce 3α-acetoxytrop-6-ene, could be done in three different ways.

[[Image:Route1-2.gif]]

[[Image:route3.gif]]

This shows how the enantiomer of hyoscine is made:

[[image:Synthesis_Scopolamine.gif]] [http://www.ucalgary.ca/~bali/chem353/project/00final/00final.htm#chemistry]

==NMR Spectrum==

'''C-NMR'''

[[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
|-
|}

'''H-NMR'''

[[image:H-NMR_Scopolamine.gif]] [http://www.ucalgary.ca/~bali/chem353/project/00final/00final.htm#chemistry]

==Uses of Hycocine==

Scopolamine is the main ingredient in skin patches marketed as "Tranderm Scop" [[1]], which are skin patches that can prevent nausea and vomitting caused by motion sickness.

The drug scopolamine is sold under the brand name of Scopace®. It is marketed to help prevent nausea and vomiting often caused by motion sickness. For this purpose it is sold over the counter but some doctors may use it to help ease the symptoms of irritable bowel, intestinal problems, parkinsonism, spastic muscle states, divertisulitis, to name a few.
[[Image:Scopace.GIF|thumb|Description]]

==Hyoscine derivative: '''Hyoscine-N-Butylbromide'''==

There is a derivative of Hyoscine called: '''Hyoscine-N-Butylbromide'''. This compound derivative can be obtained from the leaves of the Duboisia tree in Australia (ref 8).

[[Image:vlrawleaves.gif]]
Raw Duboisia leaves

[[Image:vlduboisiatree.jpg]]
Duboisia tree shrubs

The structure of this derivative:
[[Image:vlhyoscinederivative.gif]]

<jmol>
<jmolApplet>
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<color>black</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 H 0 -4.700 -0.815 0.156 0.00 0.00 H+0
ATOM 2 C 0 -4.102 -0.014 -0.277 0.00 0.00 C+0
ATOM 3 O 0 -2.875 -0.567 -0.821 0.00 0.00 O+0
ATOM 4 C 0 -2.330 -1.663 -0.270 0.00 0.00 C+0
ATOM 5 C 0 -1.057 -2.238 -0.834 0.00 0.00 C+0
ATOM 6 C 0 -0.660 -3.456 -0.041 0.00 0.00 C+0
ATOM 7 C 0 0.556 -3.488 0.614 0.00 0.00 C+0
ATOM 8 C 0 0.920 -4.606 1.342 0.00 0.00 C+0
ATOM 9 C 0 0.067 -5.691 1.414 0.00 0.00 C+0
ATOM 10 C 0 -1.150 -5.659 0.760 0.00 0.00 C+0
ATOM 11 C 0 -1.511 -4.544 0.026 0.00 0.00 C+0
ATOM 12 C 0 -1.279 -2.631 -2.296 0.00 0.00 C+0
ATOM 13 O 0 -1.541 -1.459 -3.070 0.00 0.00 O+0
ATOM 14 H 0 -0.264 -1.492 -0.775 0.00 0.00 H+0
ATOM 15 O 0 -2.862 -2.189 0.680 0.00 0.00 O+0
ATOM 16 C 0 -4.895 0.666 -1.397 0.00 0.00 C+0
ATOM 17 C 0 -6.113 1.375 -0.784 0.00 0.00 C+0
ATOM 18 C 0 -6.805 0.381 0.177 0.00 0.00 C+0
ATOM 19 O 0 -5.999 -0.624 0.795 0.00 0.00 O+0
ATOM 20 C 0 -6.106 0.593 1.536 0.00 0.00 C+0
ATOM 21 C 0 -5.055 1.696 1.272 0.00 0.00 C+0
ATOM 22 C 0 -3.761 1.011 0.809 0.00 0.00 C+0
ATOM 23 N 0 -5.597 2.447 0.108 0.00 0.00 N+1
ATOM 24 C 0 -4.531 3.206 -0.559 0.00 0.00 C+0
ATOM 25 C 0 -3.972 4.255 0.405 0.00 0.00 C+0
ATOM 26 C 0 -2.862 5.046 -0.290 0.00 0.00 C+0
ATOM 27 C 0 -2.303 6.095 0.674 0.00 0.00 C+0
ATOM 28 C 0 -6.685 3.339 0.529 0.00 0.00 C+0
ATOM 29 Br 0 14.489 1.142 0.058 0.00 0.00 Br-1
ATOM 30 H 0 1.223 -2.641 0.558 0.00 0.00 H+0
ATOM 31 H 0 1.871 -4.631 1.853 0.00 0.00 H+0
ATOM 32 H 0 0.351 -6.565 1.982 0.00 0.00 H+0
ATOM 33 H 0 -1.816 -6.507 0.816 0.00 0.00 H+0
ATOM 34 H 0 -2.462 -4.519 -0.485 0.00 0.00 H+0
ATOM 35 H 0 -0.387 -3.127 -2.679 0.00 0.00 H+0
ATOM 36 H 0 -2.130 -3.309 -2.365 0.00 0.00 H+0
ATOM 37 H 0 -1.675 -1.750 -3.983 0.00 0.00 H+0
ATOM 38 H 0 -4.262 1.397 -1.900 0.00 0.00 H+0
ATOM 39 H 0 -5.231 -0.084 -2.113 0.00 0.00 H+0
ATOM 40 H 0 -6.794 1.753 -1.546 0.00 0.00 H+0
ATOM 41 H 0 -7.879 0.227 0.067 0.00 0.00 H+0
ATOM 42 H 0 -6.649 0.610 2.481 0.00 0.00 H+0
ATOM 43 H 0 -4.895 2.330 2.145 0.00 0.00 H+0
ATOM 44 H 0 -3.293 0.505 1.653 0.00 0.00 H+0
ATOM 45 H 0 -3.077 1.757 0.404 0.00 0.00 H+0
ATOM 46 H 0 -3.733 2.527 -0.859 0.00 0.00 H+0
ATOM 47 H 0 -4.936 3.703 -1.441 0.00 0.00 H+0
ATOM 48 H 0 -4.770 4.935 0.705 0.00 0.00 H+0
ATOM 49 H 0 -3.567 3.759 1.287 0.00 0.00 H+0
ATOM 50 H 0 -2.065 4.367 -0.590 0.00 0.00 H+0
ATOM 51 H 0 -3.267 5.543 -1.172 0.00 0.00 H+0
ATOM 52 H 0 -3.101 6.775 0.974 0.00 0.00 H+0
ATOM 53 H 0 -1.898 5.598 1.556 0.00 0.00 H+0
ATOM 54 H 0 -1.513 6.659 0.179 0.00 0.00 H+0
ATOM 55 H 0 -6.308 4.051 1.263 0.00 0.00 H+0
ATOM 56 H 0 -7.068 3.879 -0.337 0.00 0.00 H+0
ATOM 57 H 0 -7.487 2.749 0.973 0.00 0.00 H+0
CONECT 2 1 22 3 16 NONE 62
CONECT 3 2 4 0 0 NONE 63
CONECT 4 3 5 15 0 NONE 64
CONECT 5 4 6 12 14 NONE 65
CONECT 6 5 11 7 0 NONE 66
CONECT 7 6 8 30 0 NONE 67
CONECT 8 7 9 31 0 NONE 68
CONECT 9 8 10 32 0 NONE 69
CONECT 10 9 11 33 0 NONE 70
CONECT 11 10 6 34 0 NONE 71
CONECT 12 5 13 35 36 NONE 72
CONECT 13 12 37 0 0 NONE 73
CONECT 15 4 0 0 0 NONE 74
CONECT 16 2 17 38 39 NONE 75
CONECT 17 16 23 18 40 NONE 76
CONECT 18 17 20 19 41 NONE 77
CONECT 19 18 20 0 0 NONE 78
CONECT 20 19 18 21 42 NONE 79
CONECT 21 20 22 23 43 NONE 80
CONECT 22 21 2 44 45 NONE 81
CONECT 23 21 17 24 28 NONE 82
CONECT 24 23 25 46 47 NONE 83
CONECT 25 24 26 48 49 NONE 84
CONECT 26 25 27 50 51 NONE 85
CONECT 27 26 52 53 54 NONE 86
CONECT 28 23 55 56 57 NONE 87
END NONE 88</inlineContents>
</jmolApplet>
</jmol>

Above: 3D structure of Hyoscine-N-Butylbromide

This derivative is used to treat bowel diseases. Like Hysocine, this drug can relax the muscle lining of the gastrointestinal and urinary tracts, to reduce spasms and involuntary movements.

==History of Hycocine==

Before the discovery of the various anesthetic agents people underwent severe pain and agony. Patients were strapped down or were given alcohol and other sedative drugs to ameliorate the pain of surgery.

Despite hycocine's high toxicity, at suitable doses this substance has beneficial medicinal effects, which were recognized in folk medicine throughout the world, and later on in scientific medicine.

Hycocine is a popular poison used in classic literature, due to it's presence in a number of plants. Its toxic properties, regardless of whether it is administered internally or externally, makes it a highly useful drug for
physicians and poisoners alike!

Hyoscine in the form of nightshade was also used by practitioners of witchcraft in the concocting of flying potions – large amounts
of it caused hallucination and a sensation of floating.

Scopolamine was first isolated by Albert Ladenburg, in the late 1800's. He isolated it as a racemic mixture with Hyoscine.

[[Image:Racemic_mixture.GIF]]

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 C 0 3.453 2.304 0.685 0.00 0.00 C+0
ATOM 2 N 0 2.834 1.011 0.364 0.00 0.00 N+0
ATOM 3 C 0 3.140 0.731 -1.050 0.00 0.00 C+0
ATOM 4 C 0 4.049 -0.415 -0.670 0.00 0.00 C+0
ATOM 5 C 0 3.779 -0.036 0.796 0.00 0.00 C+0
ATOM 6 C 0 3.013 -1.211 1.448 0.00 0.00 C+0
ATOM 7 C 0 1.803 -1.504 0.547 0.00 0.00 C+0
ATOM 8 O 0 0.905 -0.362 0.569 0.00 0.00 O+0
ATOM 9 C 0 -0.415 -0.542 0.402 0.00 0.00 C+0
ATOM 10 C 0 -1.346 0.642 0.425 0.00 0.00 C+0
ATOM 11 H 0 -1.269 1.147 1.388 0.00 0.00 H+0
ATOM 12 C 0 -2.762 0.172 0.217 0.00 0.00 C+0
ATOM 13 C 0 -3.720 0.412 1.184 0.00 0.00 C+0
ATOM 14 C 0 -5.019 -0.020 0.993 0.00 0.00 C+0
ATOM 15 C 0 -5.361 -0.691 -0.166 0.00 0.00 C+0
ATOM 16 C 0 -4.404 -0.930 -1.134 0.00 0.00 C+0
ATOM 17 C 0 -3.105 -0.495 -0.945 0.00 0.00 C+0
ATOM 18 C 0 -0.962 1.615 -0.693 0.00 0.00 C+0
ATOM 19 O 0 -1.769 2.790 -0.599 0.00 0.00 O+0
ATOM 20 O 0 -0.856 -1.654 0.234 0.00 0.00 O+0
ATOM 21 C 0 2.236 -1.777 -0.892 0.00 0.00 C+0
ATOM 22 O 0 2.879 -0.629 -1.443 0.00 0.00 O+0
ATOM 23 H 0 3.037 3.076 0.039 0.00 0.00 H+0
ATOM 24 H 0 3.253 2.554 1.727 0.00 0.00 H+0
ATOM 25 H 0 4.530 2.240 0.527 0.00 0.00 H+0
ATOM 26 H 0 3.229 1.522 -1.779 0.00 0.00 H+0
ATOM 27 H 0 5.025 -0.717 -1.017 0.00 0.00 H+0
ATOM 28 H 0 4.633 0.313 1.349 0.00 0.00 H+0
ATOM 29 H 0 3.649 -2.091 1.502 0.00 0.00 H+0
ATOM 30 H 0 2.669 -0.932 2.441 0.00 0.00 H+0
ATOM 31 H 0 1.277 -2.379 0.934 0.00 0.00 H+0
ATOM 32 H 0 -3.453 0.936 2.090 0.00 0.00 H+0
ATOM 33 H 0 -5.767 0.167 1.750 0.00 0.00 H+0
ATOM 34 H 0 -6.376 -1.029 -0.315 0.00 0.00 H+0
ATOM 35 H 0 -4.671 -1.455 -2.039 0.00 0.00 H+0
ATOM 36 H 0 -2.357 -0.682 -1.701 0.00 0.00 H+0
ATOM 37 H 0 0.089 1.886 -0.593 0.00 0.00 H+0
ATOM 38 H 0 -1.124 1.139 -1.660 0.00 0.00 H+0
ATOM 39 H 0 -1.495 3.375 -1.319 0.00 0.00 H+0
ATOM 40 H 0 2.928 -2.620 -0.907 0.00 0.00 H+0
ATOM 41 H 0 1.358 -2.021 -1.492 0.00 0.00 H+0
CONECT 1 2 23 24 25 NONE 46
CONECT 2 1 5 3 0 NONE 47
CONECT 3 2 22 4 26 NONE 48
CONECT 4 3 22 5 27 NONE 49
CONECT 5 4 2 6 28 NONE 50
CONECT 6 5 7 29 30 NONE 51
CONECT 7 6 8 21 31 NONE 52
CONECT 8 7 9 0 0 NONE 53
CONECT 9 8 10 20 0 NONE 54
CONECT 10 9 11 12 18 NONE 55
CONECT 12 10 17 13 0 NONE 56
CONECT 13 12 14 32 0 NONE 57
CONECT 14 13 15 33 0 NONE 58
CONECT 15 14 16 34 0 NONE 59
CONECT 16 15 17 35 0 NONE 60
CONECT 17 16 12 36 0 NONE 61
CONECT 18 10 19 37 38 NONE 62
CONECT 19 18 39 0 0 NONE 63
CONECT 20 9 0 0 0 NONE 64
CONECT 21 7 22 40 41 NONE 65
CONECT 22 21 3 4 0 NONE 66
END NONE 67
</inlineContents>
</jmolApplet>
</jmol>

Above: 3d structure of (+)-scopolamine

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 C 0 3.447 2.197 -0.621 0.00 0.00 C+0
ATOM 2 N 0 2.783 0.921 -0.328 0.00 0.00 N+0
ATOM 3 C 0 3.100 0.010 -1.442 0.00 0.00 C+0
ATOM 4 C 0 3.959 -0.855 -0.548 0.00 0.00 C+0
ATOM 5 C 0 3.680 0.167 0.568 0.00 0.00 C+0
ATOM 6 C 0 2.859 -0.552 1.664 0.00 0.00 C+0
ATOM 7 C 0 1.653 -1.195 0.963 0.00 0.00 C+0
ATOM 8 O 0 0.800 -0.148 0.426 0.00 0.00 O+0
ATOM 9 C 0 -0.523 -0.349 0.320 0.00 0.00 C+0
ATOM 10 C 0 -1.408 0.736 -0.237 0.00 0.00 C+0
ATOM 11 H 0 -1.095 0.974 -1.254 0.00 0.00 H+0
ATOM 12 C 0 -2.838 0.261 -0.249 0.00 0.00 C+0
ATOM 13 C 0 -3.531 0.187 -1.443 0.00 0.00 C+0
ATOM 14 C 0 -4.843 -0.248 -1.454 0.00 0.00 C+0
ATOM 15 C 0 -5.462 -0.610 -0.272 0.00 0.00 C+0
ATOM 16 C 0 -4.768 -0.537 0.922 0.00 0.00 C+0
ATOM 17 C 0 -3.455 -0.106 0.932 0.00 0.00 C+0
ATOM 18 C 0 -1.293 1.986 0.638 0.00 0.00 C+0
ATOM 19 O 0 0.037 2.504 0.557 0.00 0.00 O+0
ATOM 20 O 0 -1.004 -1.401 0.671 0.00 0.00 O+0
ATOM 21 C 0 2.097 -2.115 -0.173 0.00 0.00 C+0
ATOM 22 O 0 2.793 -1.370 -1.171 0.00 0.00 O+0
ATOM 23 H 0 3.071 2.594 -1.564 0.00 0.00 H+0
ATOM 24 H 0 3.241 2.907 0.180 0.00 0.00 H+0
ATOM 25 H 0 4.523 2.039 -0.697 0.00 0.00 H+0
ATOM 26 H 0 3.232 0.370 -2.451 0.00 0.00 H+0
ATOM 27 H 0 4.927 -1.309 -0.685 0.00 0.00 H+0
ATOM 28 H 0 4.539 0.709 0.925 0.00 0.00 H+0
ATOM 29 H 0 3.459 -1.324 2.139 0.00 0.00 H+0
ATOM 30 H 0 2.511 0.164 2.405 0.00 0.00 H+0
ATOM 31 H 0 1.087 -1.777 1.693 0.00 0.00 H+0
ATOM 32 H 0 -3.048 0.470 -2.366 0.00 0.00 H+0
ATOM 33 H 0 -5.385 -0.305 -2.386 0.00 0.00 H+0
ATOM 34 H 0 -6.487 -0.950 -0.281 0.00 0.00 H+0
ATOM 35 H 0 -5.251 -0.819 1.845 0.00 0.00 H+0
ATOM 36 H 0 -2.913 -0.048 1.865 0.00 0.00 H+0
ATOM 37 H 0 -1.998 2.740 0.288 0.00 0.00 H+0
ATOM 38 H 0 -1.520 1.728 1.672 0.00 0.00 H+0
ATOM 39 H 0 0.066 3.289 1.121 0.00 0.00 H+0
ATOM 40 H 0 2.756 -2.887 0.225 0.00 0.00 H+0
ATOM 41 H 0 1.220 -2.585 -0.620 0.00 0.00 H+0
CONECT 1 2 23 24 25 NONE 46
CONECT 2 1 5 3 0 NONE 47
CONECT 3 2 22 4 26 NONE 48
CONECT 4 3 22 5 27 NONE 49
CONECT 5 4 2 6 28 NONE 50
CONECT 6 5 7 29 30 NONE 51
CONECT 7 6 8 21 31 NONE 52
CONECT 8 7 9 0 0 NONE 53
CONECT 9 8 10 20 0 NONE 54
CONECT 10 9 11 12 18 NONE 55
CONECT 12 10 17 13 0 NONE 56
CONECT 13 12 14 32 0 NONE 57
CONECT 14 13 15 33 0 NONE 58
CONECT 15 14 16 34 0 NONE 59
CONECT 16 15 17 35 0 NONE 60
CONECT 17 16 12 36 0 NONE 61
CONECT 18 10 19 37 38 NONE 62
CONECT 19 18 39 0 0 NONE 63
CONECT 20 9 0 0 0 NONE 64
CONECT 21 7 22 40 41 NONE 65
CONECT 22 21 3 4 0 NONE 66
END NONE 67
</inlineContents>
</jmolApplet>
</jmol>

Above: 3d structure of (-)-scopolamine (the only difference in comparison to the other enantiomer, is the geometry of the CH<sub>2</sub>OH group near the phenyl ring)

This was discovered when Ladenburg was crystalising hyoscyamine from exctracts of the plant Hyoseyamus and found that an alkaloid still remained in the solution. This alkaloid had never previously been isolated and up to this day was considered to be a waste product by scientists.

[[Image:Hyoseyamus.jpg]] Hyoseyamus (Ref 3)

To completely isolate the molecule, further purification was required, by further recrystallisation. Ladenburg also found that hyoscine decomposed to a froth at 196 to 198<sup>o</sup>C

=Recent history=
In August 2006 a chemical company from Queensland, Australia was being investigated by the Australian Federal Police over fears that a 100-kilogram shipment of hyoscine was diverted to Iraq. Documents from 2002 showed that the federal police questioned the company, Alkaloids of Australia, about a shipment of hyoscine, that was sent to the Syrian pharmaceutical company Ibn Hayan in 2001. US and British military reports show that hyoscine can also be used an "incapacitating agent", causing severe symptoms such as impaired vision, temporary delirium and an abnormally rapid heartbeat. Reports by the US Army show that an injection of as little as 1.5 milligrams of scopolamine hydrobromide can cause a soldier to become delirious for two to four hours. (Ref 4)

==References==

1. http://www.prevent-motion-sickness-scopolamine.com/

2. Savary, B. J. and D. K. Dougall. "Scopolamine Radioimmunoassay for Tissue- cultures of Datura." Phytochemistry 29.5 (1990): 1567-69.

3. http://ag.msu.montana.edu/cipm/cipmpics.asp?type=thumb&flag=1&id=144

4. http://www.theage.com.au/news/investigations/probe-over-nerve-gas-suspicion/2006/08/20/1156012411533.html

5. E. Leete et. al. "Use of Carbon- 13 Nuclear Magnetic Resonance to establish that the biosynthesis of tropic acid involves an intramolecular rearrangement of phenylalanine." Journal of the American Chemical Society, 1975

*[http://www.plantcell.org/cgi/reprint/7/7/1059.pdf/ Alkaloid Synthesis]- Tropane and Nicotine Alkaloids

6. http://www.drugdelivery.ca/s3557-s-HYOSCINE.aspx

7. http://www.hopepharm.com/motion/index.html

8. http://www.linnea-worldwide.com/products/hyoscine.asp

It:Hycocine

2006-10-26T15:55:59Z

Vl105: /* History of Hycocine */

== '''HYOSCINE''' ==

{| 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 that 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).

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<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 it 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. They studied the accumulation of scopolamine in cell and tissue cultures of Datura as a way of seeing on a biochemical level how the natural products scopolamine and hyoscyamine accumulate in plants of the Datura family. (Ref 2)

[[Image:Datura.jpg|thumb|''Datura wrightii'' ]] ''Datura wrightii''

Scopolamine can be isolated from plants by extraction:

[[Image:Biosynthesis_of_alkaloids2.GIF]] [http://www.plantcell.org/cgi/reprint/7/7/1059.pdf]

==Physical properties of Hycocine==

{| border="1"

|-
! Formula
| C1<sub>7</sub>H<sub>21</sub>NO<sub>4</sub>
|-
! Molecular weight
| 303.35
|-
! Melting point
| 59<sup>o</sup>C
|-
! Appearance
| white, amophous, semi-solid
|}

==Chemical Properties of Hycocine==

It is a drug that acts on the autonomic nervous system and prevents muscle spasm.
It is an alkaloid, obtained from various plants of the nightshade family (such as belladonna). [http://www.tiscali.co.uk/reference/encyclopaedia/hutchinson/m0014386.html]

The depressive action hycocine on the central nervous system makes it suitable for use in very tiny amounts in the treatment of
anxiety-related problems and travel-sickness (in the form of hyoscine hydrobromide, which is a type of anticholinergic drug).

In larger doses, it breaks down a person’s ability to discriminate and make reasoned judgment, making it a potential 'truth drug'.

==Effects of Hycocine==

It is frequently included in premedication to dry up lung secretions and as a postoperative sedative. It is also used to
treat ulcers, to relax the womb in labour, for travel sickness, and to dilate the pupils before an eye examination.

Hyoscine produces sedation. With higher doses it produces agitation and disorientation similar to that of atropine. Hyoscine also has a significant anti-emetic effect, and that is why it is used for the treatment of motion sickness (Rang et al., 1995)

Hyoscine induced a moderate bradycardia and a marked decrease in salivation when administered via injection. These
effects were maximal at 1 to 2 hours after administration of hyoscine but were no longer present at 4 hours.

Consistent behavioral effects of hyoscine in various experiments were a decrease in spontaneous speech and movement and a significant
decrease in energy.

When administered medically, hyoscine may cause the muscles in the eye to become relaxed, widening the pupil. Pupils may remain wide and not respond to light. They'll also be more sensitive.

Fatal doses of hyoscine causes the heart to cease functioning, which results in death.

There are side effects that are known to have affected patients (ref 6). The drug Hyoscine affects the autonomic nervous system so this could be the cause of those side effects:

* Dizziness
* Blurred vision
* Dry mouth
* Vomiting
* Irritation of the skin
* Problems in urinating

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''(+)-scopolamine'''
|-
! CAS Registry Number
| 51-34-3, 138-12-5, 64069-63-2, 124917-17-5
|-
! Chemical Name
|3-hydroxy-2-phenyl-propionic acid 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yl ester
|-
! Molecular Formula
| C17H21NO4
|-
! Molecular Weight
| 303.36
|-
|}

==Synthesis==

In 1957 Fodor synthesised scopolamine via 2 steps. He found that the first work up step to produce 3α-acetoxytrop-6-ene, could be done in three different ways.

[[Image:Route1-2.gif]]

[[Image:route3.gif]]

This shows how the enantiomer of hyoscine is made:

[[image:Synthesis_Scopolamine.gif]] [http://www.ucalgary.ca/~bali/chem353/project/00final/00final.htm#chemistry]

==NMR Spectrum==

'''C-NMR'''

[[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
|-
|}

'''H-NMR'''

[[image:H-NMR_Scopolamine.gif]] [http://www.ucalgary.ca/~bali/chem353/project/00final/00final.htm#chemistry]

==Uses of Hycocine==

Scopolamine is the main ingredient in skin patches marketed as "Tranderm Scop" [[1]], which are skin patches that can prevent nausea and vomitting caused by motion sickness.

The drug scopolamine is sold under the brand name of Scopace®. It is marketed to help prevent nausea and vomiting often caused by motion sickness. For this purpose it is sold over the counter but some doctors may use it to help ease the symptoms of irritable bowel, intestinal problems, parkinsonism, spastic muscle states, divertisulitis, to name a few.
[[Image:Scopace.GIF|thumb|Description]]

==Hyoscine derivative: '''Hyoscine-N-Butylbromide'''==

There is a derivative of Hyoscine called: '''Hyoscine-N-Butylbromide'''. This compound derivative can be obtained from the leaves of the Duboisia tree in Australia (ref 8).

[[Image:vlrawleaves.gif]]
Raw Duboisia leaves

[[Image:vlduboisiatree.jpg]]
Duboisia tree shrubs

The structure of this derivative:
[[Image:vlhyoscinederivative.gif]]

<jmol>
<jmolApplet>
<size>400</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>ATOM 1 H 0 -4.700 -0.815 0.156 0.00 0.00 H+0
ATOM 2 C 0 -4.102 -0.014 -0.277 0.00 0.00 C+0
ATOM 3 O 0 -2.875 -0.567 -0.821 0.00 0.00 O+0
ATOM 4 C 0 -2.330 -1.663 -0.270 0.00 0.00 C+0
ATOM 5 C 0 -1.057 -2.238 -0.834 0.00 0.00 C+0
ATOM 6 C 0 -0.660 -3.456 -0.041 0.00 0.00 C+0
ATOM 7 C 0 0.556 -3.488 0.614 0.00 0.00 C+0
ATOM 8 C 0 0.920 -4.606 1.342 0.00 0.00 C+0
ATOM 9 C 0 0.067 -5.691 1.414 0.00 0.00 C+0
ATOM 10 C 0 -1.150 -5.659 0.760 0.00 0.00 C+0
ATOM 11 C 0 -1.511 -4.544 0.026 0.00 0.00 C+0
ATOM 12 C 0 -1.279 -2.631 -2.296 0.00 0.00 C+0
ATOM 13 O 0 -1.541 -1.459 -3.070 0.00 0.00 O+0
ATOM 14 H 0 -0.264 -1.492 -0.775 0.00 0.00 H+0
ATOM 15 O 0 -2.862 -2.189 0.680 0.00 0.00 O+0
ATOM 16 C 0 -4.895 0.666 -1.397 0.00 0.00 C+0
ATOM 17 C 0 -6.113 1.375 -0.784 0.00 0.00 C+0
ATOM 18 C 0 -6.805 0.381 0.177 0.00 0.00 C+0
ATOM 19 O 0 -5.999 -0.624 0.795 0.00 0.00 O+0
ATOM 20 C 0 -6.106 0.593 1.536 0.00 0.00 C+0
ATOM 21 C 0 -5.055 1.696 1.272 0.00 0.00 C+0
ATOM 22 C 0 -3.761 1.011 0.809 0.00 0.00 C+0
ATOM 23 N 0 -5.597 2.447 0.108 0.00 0.00 N+1
ATOM 24 C 0 -4.531 3.206 -0.559 0.00 0.00 C+0
ATOM 25 C 0 -3.972 4.255 0.405 0.00 0.00 C+0
ATOM 26 C 0 -2.862 5.046 -0.290 0.00 0.00 C+0
ATOM 27 C 0 -2.303 6.095 0.674 0.00 0.00 C+0
ATOM 28 C 0 -6.685 3.339 0.529 0.00 0.00 C+0
ATOM 29 Br 0 14.489 1.142 0.058 0.00 0.00 Br-1
ATOM 30 H 0 1.223 -2.641 0.558 0.00 0.00 H+0
ATOM 31 H 0 1.871 -4.631 1.853 0.00 0.00 H+0
ATOM 32 H 0 0.351 -6.565 1.982 0.00 0.00 H+0
ATOM 33 H 0 -1.816 -6.507 0.816 0.00 0.00 H+0
ATOM 34 H 0 -2.462 -4.519 -0.485 0.00 0.00 H+0
ATOM 35 H 0 -0.387 -3.127 -2.679 0.00 0.00 H+0
ATOM 36 H 0 -2.130 -3.309 -2.365 0.00 0.00 H+0
ATOM 37 H 0 -1.675 -1.750 -3.983 0.00 0.00 H+0
ATOM 38 H 0 -4.262 1.397 -1.900 0.00 0.00 H+0
ATOM 39 H 0 -5.231 -0.084 -2.113 0.00 0.00 H+0
ATOM 40 H 0 -6.794 1.753 -1.546 0.00 0.00 H+0
ATOM 41 H 0 -7.879 0.227 0.067 0.00 0.00 H+0
ATOM 42 H 0 -6.649 0.610 2.481 0.00 0.00 H+0
ATOM 43 H 0 -4.895 2.330 2.145 0.00 0.00 H+0
ATOM 44 H 0 -3.293 0.505 1.653 0.00 0.00 H+0
ATOM 45 H 0 -3.077 1.757 0.404 0.00 0.00 H+0
ATOM 46 H 0 -3.733 2.527 -0.859 0.00 0.00 H+0
ATOM 47 H 0 -4.936 3.703 -1.441 0.00 0.00 H+0
ATOM 48 H 0 -4.770 4.935 0.705 0.00 0.00 H+0
ATOM 49 H 0 -3.567 3.759 1.287 0.00 0.00 H+0
ATOM 50 H 0 -2.065 4.367 -0.590 0.00 0.00 H+0
ATOM 51 H 0 -3.267 5.543 -1.172 0.00 0.00 H+0
ATOM 52 H 0 -3.101 6.775 0.974 0.00 0.00 H+0
ATOM 53 H 0 -1.898 5.598 1.556 0.00 0.00 H+0
ATOM 54 H 0 -1.513 6.659 0.179 0.00 0.00 H+0
ATOM 55 H 0 -6.308 4.051 1.263 0.00 0.00 H+0
ATOM 56 H 0 -7.068 3.879 -0.337 0.00 0.00 H+0
ATOM 57 H 0 -7.487 2.749 0.973 0.00 0.00 H+0
CONECT 2 1 22 3 16 NONE 62
CONECT 3 2 4 0 0 NONE 63
CONECT 4 3 5 15 0 NONE 64
CONECT 5 4 6 12 14 NONE 65
CONECT 6 5 11 7 0 NONE 66
CONECT 7 6 8 30 0 NONE 67
CONECT 8 7 9 31 0 NONE 68
CONECT 9 8 10 32 0 NONE 69
CONECT 10 9 11 33 0 NONE 70
CONECT 11 10 6 34 0 NONE 71
CONECT 12 5 13 35 36 NONE 72
CONECT 13 12 37 0 0 NONE 73
CONECT 15 4 0 0 0 NONE 74
CONECT 16 2 17 38 39 NONE 75
CONECT 17 16 23 18 40 NONE 76
CONECT 18 17 20 19 41 NONE 77
CONECT 19 18 20 0 0 NONE 78
CONECT 20 19 18 21 42 NONE 79
CONECT 21 20 22 23 43 NONE 80
CONECT 22 21 2 44 45 NONE 81
CONECT 23 21 17 24 28 NONE 82
CONECT 24 23 25 46 47 NONE 83
CONECT 25 24 26 48 49 NONE 84
CONECT 26 25 27 50 51 NONE 85
CONECT 27 26 52 53 54 NONE 86
CONECT 28 23 55 56 57 NONE 87
END NONE 88</inlineContents>
</jmolApplet>
</jmol>

Above: 3D structure of Hyoscine-N-Butylbromide

This derivative is used to treat bowel diseases. Like Hysocine, this drug can relax the muscle lining of the gastrointestinal and urinary tracts, to reduce spasms and involuntary movements.

==History of Hycocine==

Before the discovery of the various anesthetic agents people underwent severe pain and agony. Patients were strapped down or were given alcohol and other sedative drugs to ameliorate the pain of surgery.

Despite hycocine's high toxicity, at suitable doses this substance has beneficial medicinal effects, which were recognized in folk medicine throughout the world, and later on in scientific medicine.

Hycocine is a popular poison used in classic literature, due to it's presence in a number of plants. Its toxic properties, regardless of whether it is administered internally or externally, makes it a highly useful drug for
physicians and poisoners alike!

Hyoscine in the form of nightshade was also used by practitioners of witchcraft in the concocting of flying potions – large amounts
of it caused hallucination and a sensation of floating.

Scopolamine was first isolated by Albert Ladenburg, in the late 1800's. He isolated it as a racemic mixture with Hyoscine.

[[Image:Racemic_mixture.GIF]]

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 C 0 3.453 2.304 0.685 0.00 0.00 C+0
ATOM 2 N 0 2.834 1.011 0.364 0.00 0.00 N+0
ATOM 3 C 0 3.140 0.731 -1.050 0.00 0.00 C+0
ATOM 4 C 0 4.049 -0.415 -0.670 0.00 0.00 C+0
ATOM 5 C 0 3.779 -0.036 0.796 0.00 0.00 C+0
ATOM 6 C 0 3.013 -1.211 1.448 0.00 0.00 C+0
ATOM 7 C 0 1.803 -1.504 0.547 0.00 0.00 C+0
ATOM 8 O 0 0.905 -0.362 0.569 0.00 0.00 O+0
ATOM 9 C 0 -0.415 -0.542 0.402 0.00 0.00 C+0
ATOM 10 C 0 -1.346 0.642 0.425 0.00 0.00 C+0
ATOM 11 H 0 -1.269 1.147 1.388 0.00 0.00 H+0
ATOM 12 C 0 -2.762 0.172 0.217 0.00 0.00 C+0
ATOM 13 C 0 -3.720 0.412 1.184 0.00 0.00 C+0
ATOM 14 C 0 -5.019 -0.020 0.993 0.00 0.00 C+0
ATOM 15 C 0 -5.361 -0.691 -0.166 0.00 0.00 C+0
ATOM 16 C 0 -4.404 -0.930 -1.134 0.00 0.00 C+0
ATOM 17 C 0 -3.105 -0.495 -0.945 0.00 0.00 C+0
ATOM 18 C 0 -0.962 1.615 -0.693 0.00 0.00 C+0
ATOM 19 O 0 -1.769 2.790 -0.599 0.00 0.00 O+0
ATOM 20 O 0 -0.856 -1.654 0.234 0.00 0.00 O+0
ATOM 21 C 0 2.236 -1.777 -0.892 0.00 0.00 C+0
ATOM 22 O 0 2.879 -0.629 -1.443 0.00 0.00 O+0
ATOM 23 H 0 3.037 3.076 0.039 0.00 0.00 H+0
ATOM 24 H 0 3.253 2.554 1.727 0.00 0.00 H+0
ATOM 25 H 0 4.530 2.240 0.527 0.00 0.00 H+0
ATOM 26 H 0 3.229 1.522 -1.779 0.00 0.00 H+0
ATOM 27 H 0 5.025 -0.717 -1.017 0.00 0.00 H+0
ATOM 28 H 0 4.633 0.313 1.349 0.00 0.00 H+0
ATOM 29 H 0 3.649 -2.091 1.502 0.00 0.00 H+0
ATOM 30 H 0 2.669 -0.932 2.441 0.00 0.00 H+0
ATOM 31 H 0 1.277 -2.379 0.934 0.00 0.00 H+0
ATOM 32 H 0 -3.453 0.936 2.090 0.00 0.00 H+0
ATOM 33 H 0 -5.767 0.167 1.750 0.00 0.00 H+0
ATOM 34 H 0 -6.376 -1.029 -0.315 0.00 0.00 H+0
ATOM 35 H 0 -4.671 -1.455 -2.039 0.00 0.00 H+0
ATOM 36 H 0 -2.357 -0.682 -1.701 0.00 0.00 H+0
ATOM 37 H 0 0.089 1.886 -0.593 0.00 0.00 H+0
ATOM 38 H 0 -1.124 1.139 -1.660 0.00 0.00 H+0
ATOM 39 H 0 -1.495 3.375 -1.319 0.00 0.00 H+0
ATOM 40 H 0 2.928 -2.620 -0.907 0.00 0.00 H+0
ATOM 41 H 0 1.358 -2.021 -1.492 0.00 0.00 H+0
CONECT 1 2 23 24 25 NONE 46
CONECT 2 1 5 3 0 NONE 47
CONECT 3 2 22 4 26 NONE 48
CONECT 4 3 22 5 27 NONE 49
CONECT 5 4 2 6 28 NONE 50
CONECT 6 5 7 29 30 NONE 51
CONECT 7 6 8 21 31 NONE 52
CONECT 8 7 9 0 0 NONE 53
CONECT 9 8 10 20 0 NONE 54
CONECT 10 9 11 12 18 NONE 55
CONECT 12 10 17 13 0 NONE 56
CONECT 13 12 14 32 0 NONE 57
CONECT 14 13 15 33 0 NONE 58
CONECT 15 14 16 34 0 NONE 59
CONECT 16 15 17 35 0 NONE 60
CONECT 17 16 12 36 0 NONE 61
CONECT 18 10 19 37 38 NONE 62
CONECT 19 18 39 0 0 NONE 63
CONECT 20 9 0 0 0 NONE 64
CONECT 21 7 22 40 41 NONE 65
CONECT 22 21 3 4 0 NONE 66
END NONE 67
</inlineContents>
</jmolApplet>
</jmol>

Above: 3d structure of (+)-scopolamine

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 C 0 3.447 2.197 -0.621 0.00 0.00 C+0
ATOM 2 N 0 2.783 0.921 -0.328 0.00 0.00 N+0
ATOM 3 C 0 3.100 0.010 -1.442 0.00 0.00 C+0
ATOM 4 C 0 3.959 -0.855 -0.548 0.00 0.00 C+0
ATOM 5 C 0 3.680 0.167 0.568 0.00 0.00 C+0
ATOM 6 C 0 2.859 -0.552 1.664 0.00 0.00 C+0
ATOM 7 C 0 1.653 -1.195 0.963 0.00 0.00 C+0
ATOM 8 O 0 0.800 -0.148 0.426 0.00 0.00 O+0
ATOM 9 C 0 -0.523 -0.349 0.320 0.00 0.00 C+0
ATOM 10 C 0 -1.408 0.736 -0.237 0.00 0.00 C+0
ATOM 11 H 0 -1.095 0.974 -1.254 0.00 0.00 H+0
ATOM 12 C 0 -2.838 0.261 -0.249 0.00 0.00 C+0
ATOM 13 C 0 -3.531 0.187 -1.443 0.00 0.00 C+0
ATOM 14 C 0 -4.843 -0.248 -1.454 0.00 0.00 C+0
ATOM 15 C 0 -5.462 -0.610 -0.272 0.00 0.00 C+0
ATOM 16 C 0 -4.768 -0.537 0.922 0.00 0.00 C+0
ATOM 17 C 0 -3.455 -0.106 0.932 0.00 0.00 C+0
ATOM 18 C 0 -1.293 1.986 0.638 0.00 0.00 C+0
ATOM 19 O 0 0.037 2.504 0.557 0.00 0.00 O+0
ATOM 20 O 0 -1.004 -1.401 0.671 0.00 0.00 O+0
ATOM 21 C 0 2.097 -2.115 -0.173 0.00 0.00 C+0
ATOM 22 O 0 2.793 -1.370 -1.171 0.00 0.00 O+0
ATOM 23 H 0 3.071 2.594 -1.564 0.00 0.00 H+0
ATOM 24 H 0 3.241 2.907 0.180 0.00 0.00 H+0
ATOM 25 H 0 4.523 2.039 -0.697 0.00 0.00 H+0
ATOM 26 H 0 3.232 0.370 -2.451 0.00 0.00 H+0
ATOM 27 H 0 4.927 -1.309 -0.685 0.00 0.00 H+0
ATOM 28 H 0 4.539 0.709 0.925 0.00 0.00 H+0
ATOM 29 H 0 3.459 -1.324 2.139 0.00 0.00 H+0
ATOM 30 H 0 2.511 0.164 2.405 0.00 0.00 H+0
ATOM 31 H 0 1.087 -1.777 1.693 0.00 0.00 H+0
ATOM 32 H 0 -3.048 0.470 -2.366 0.00 0.00 H+0
ATOM 33 H 0 -5.385 -0.305 -2.386 0.00 0.00 H+0
ATOM 34 H 0 -6.487 -0.950 -0.281 0.00 0.00 H+0
ATOM 35 H 0 -5.251 -0.819 1.845 0.00 0.00 H+0
ATOM 36 H 0 -2.913 -0.048 1.865 0.00 0.00 H+0
ATOM 37 H 0 -1.998 2.740 0.288 0.00 0.00 H+0
ATOM 38 H 0 -1.520 1.728 1.672 0.00 0.00 H+0
ATOM 39 H 0 0.066 3.289 1.121 0.00 0.00 H+0
ATOM 40 H 0 2.756 -2.887 0.225 0.00 0.00 H+0
ATOM 41 H 0 1.220 -2.585 -0.620 0.00 0.00 H+0
CONECT 1 2 23 24 25 NONE 46
CONECT 2 1 5 3 0 NONE 47
CONECT 3 2 22 4 26 NONE 48
CONECT 4 3 22 5 27 NONE 49
CONECT 5 4 2 6 28 NONE 50
CONECT 6 5 7 29 30 NONE 51
CONECT 7 6 8 21 31 NONE 52
CONECT 8 7 9 0 0 NONE 53
CONECT 9 8 10 20 0 NONE 54
CONECT 10 9 11 12 18 NONE 55
CONECT 12 10 17 13 0 NONE 56
CONECT 13 12 14 32 0 NONE 57
CONECT 14 13 15 33 0 NONE 58
CONECT 15 14 16 34 0 NONE 59
CONECT 16 15 17 35 0 NONE 60
CONECT 17 16 12 36 0 NONE 61
CONECT 18 10 19 37 38 NONE 62
CONECT 19 18 39 0 0 NONE 63
CONECT 20 9 0 0 0 NONE 64
CONECT 21 7 22 40 41 NONE 65
CONECT 22 21 3 4 0 NONE 66
END NONE 67
</inlineContents>
</jmolApplet>
</jmol>

Above: 3d structure of (-)-scopolamine

This was discovered when Ladenburg was crystalising hyoscyamine from exctracts of the plant Hyoseyamus and found that an alkaloid still remained in the solution. This alkaloid had never previously been isolated and up to this day was considered to be a waste product by scientists.

[[Image:Hyoseyamus.jpg]] Hyoseyamus (Ref 3)

To completely isolate the molecule, further purification was required, by further recrystallisation. Ladenburg also found that hyoscine decomposed to a froth at 196 to 198<sup>o</sup>C

=Recent history=
In August 2006 a chemical company from Queensland, Australia was being investigated by the Australian Federal Police over fears that a 100-kilogram shipment of hyoscine was diverted to Iraq. Documents from 2002 showed that the federal police questioned the company, Alkaloids of Australia, about a shipment of hyoscine, that was sent to the Syrian pharmaceutical company Ibn Hayan in 2001. US and British military reports show that hyoscine can also be used an "incapacitating agent", causing severe symptoms such as impaired vision, temporary delirium and an abnormally rapid heartbeat. Reports by the US Army show that an injection of as little as 1.5 milligrams of scopolamine hydrobromide can cause a soldier to become delirious for two to four hours. (Ref 4)

==References==

1. http://www.prevent-motion-sickness-scopolamine.com/

2. Savary, B. J. and D. K. Dougall. "Scopolamine Radioimmunoassay for Tissue- cultures of Datura." Phytochemistry 29.5 (1990): 1567-69.

3. http://ag.msu.montana.edu/cipm/cipmpics.asp?type=thumb&flag=1&id=144

4. http://www.theage.com.au/news/investigations/probe-over-nerve-gas-suspicion/2006/08/20/1156012411533.html

5. E. Leete et. al. "Use of Carbon- 13 Nuclear Magnetic Resonance to establish that the biosynthesis of tropic acid involves an intramolecular rearrangement of phenylalanine." Journal of the American Chemical Society, 1975

*[http://www.plantcell.org/cgi/reprint/7/7/1059.pdf/ Alkaloid Synthesis]- Tropane and Nicotine Alkaloids

6. http://www.drugdelivery.ca/s3557-s-HYOSCINE.aspx

7. http://www.hopepharm.com/motion/index.html

8. http://www.linnea-worldwide.com/products/hyoscine.asp

It:Hycocine

2006-10-26T15:48:02Z

Vl105: /* History of Hycocine */

== '''HYOSCINE''' ==

{| 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 that 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 it 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. They studied the accumulation of scopolamine in cell and tissue cultures of Datura as a way of seeing on a biochemical level how the natural products scopolamine and hyoscyamine accumulate in plants of the Datura family. (Ref 2)

[[Image:Datura.jpg|thumb|''Datura wrightii'' ]] ''Datura wrightii''

Scopolamine can be isolated from plants by extraction:

[[Image:Biosynthesis_of_alkaloids2.GIF]] [http://www.plantcell.org/cgi/reprint/7/7/1059.pdf]

==Physical properties of Hycocine==

{| border="1"

|-
! Formula
| C1<sub>7</sub>H<sub>21</sub>NO<sub>4</sub>
|-
! Molecular weight
| 303.35
|-
! Melting point
| 59<sup>o</sup>C
|-
! Appearance
| white, amophous, semi-solid
|}

==Chemical Properties of Hycocine==

It is a drug that acts on the autonomic nervous system and prevents muscle spasm.
It is an alkaloid, obtained from various plants of the nightshade family (such as belladonna). [http://www.tiscali.co.uk/reference/encyclopaedia/hutchinson/m0014386.html]

The depressive action hycocine on the central nervous system makes it suitable for use in very tiny amounts in the treatment of
anxiety-related problems and travel-sickness (in the form of hyoscine hydrobromide, which is a type of anticholinergic drug).

In larger doses, it breaks down a person’s ability to discriminate and make reasoned judgment, making it a potential 'truth drug'.

==Effects of Hycocine==

It is frequently included in premedication to dry up lung secretions and as a postoperative sedative. It is also used to
treat ulcers, to relax the womb in labour, for travel sickness, and to dilate the pupils before an eye examination.

Hyoscine produces sedation. With higher doses it produces agitation and disorientation similar to that of atropine. Hyoscine also has a significant anti-emetic effect, and that is why it is used for the treatment of motion sickness (Rang et al., 1995)

Hyoscine induced a moderate bradycardia and a marked decrease in salivation when administered via injection. These
effects were maximal at 1 to 2 hours after administration of hyoscine but were no longer present at 4 hours.

Consistent behavioral effects of hyoscine in various experiments were a decrease in spontaneous speech and movement and a significant
decrease in energy.

When administered medically, hyoscine may cause the muscles in the eye to become relaxed, widening the pupil. Pupils may remain wide and not respond to light. They'll also be more sensitive.

Fatal doses of hyoscine causes the heart to cease functioning, which results in death.

There are side effects that are known to have affected patients (ref 6). The drug Hyoscine affects the autonomic nervous system so this could be the cause of those side effects:

* Dizziness
* Blurred vision
* Dry mouth
* Vomiting
* Irritation of the skin
* Problems in urinating

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''(+)-scopolamine'''
|-
! CAS Registry Number
| 51-34-3, 138-12-5, 64069-63-2, 124917-17-5
|-
! Chemical Name
|3-hydroxy-2-phenyl-propionic acid 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yl ester
|-
! Molecular Formula
| C17H21NO4
|-
! Molecular Weight
| 303.36
|-
|}

==Synthesis==

In 1957 Fodor synthesised scopolamine via 2 steps. He found that the first work up step to produce 3α-acetoxytrop-6-ene, could be done in three different ways.

[[Image:Route1-2.gif]]

[[Image:route3.gif]]

This shows how the enantiomer of hyoscine is made:

[[image:Synthesis_Scopolamine.gif]] [http://www.ucalgary.ca/~bali/chem353/project/00final/00final.htm#chemistry]

==NMR Spectrum==

'''C-NMR'''

[[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
|-
|}

'''H-NMR'''

[[image:H-NMR_Scopolamine.gif]] [http://www.ucalgary.ca/~bali/chem353/project/00final/00final.htm#chemistry]

==Uses of Hycocine==

Scopolamine is the main ingredient in skin patches marketed as "Tranderm Scop" [[1]], which are skin patches that can prevent nausea and vomitting caused by motion sickness.

The drug scopolamine is sold under the brand name of Scopace®. It is marketed to help prevent nausea and vomiting often caused by motion sickness. For this purpose it is sold over the counter but some doctors may use it to help ease the symptoms of irritable bowel, intestinal problems, parkinsonism, spastic muscle states, divertisulitis, to name a few.
[[Image:Scopace.GIF|thumb|Description]]

==Hyoscine derivative: '''Hyoscine-N-Butylbromide'''==

There is a derivative of Hyoscine called: '''Hyoscine-N-Butylbromide'''. This compound derivative can be obtained from the leaves of the Duboisia tree in Australia (ref 8).

[[Image:vlrawleaves.gif]]
Raw Duboisia leaves

[[Image:vlduboisiatree.jpg]]
Duboisia tree shrubs

The structure of this derivative:
[[Image:vlhyoscinederivative.gif]]

<jmol>
<jmolApplet>
<size>400</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>ATOM 1 H 0 -4.700 -0.815 0.156 0.00 0.00 H+0
ATOM 2 C 0 -4.102 -0.014 -0.277 0.00 0.00 C+0
ATOM 3 O 0 -2.875 -0.567 -0.821 0.00 0.00 O+0
ATOM 4 C 0 -2.330 -1.663 -0.270 0.00 0.00 C+0
ATOM 5 C 0 -1.057 -2.238 -0.834 0.00 0.00 C+0
ATOM 6 C 0 -0.660 -3.456 -0.041 0.00 0.00 C+0
ATOM 7 C 0 0.556 -3.488 0.614 0.00 0.00 C+0
ATOM 8 C 0 0.920 -4.606 1.342 0.00 0.00 C+0
ATOM 9 C 0 0.067 -5.691 1.414 0.00 0.00 C+0
ATOM 10 C 0 -1.150 -5.659 0.760 0.00 0.00 C+0
ATOM 11 C 0 -1.511 -4.544 0.026 0.00 0.00 C+0
ATOM 12 C 0 -1.279 -2.631 -2.296 0.00 0.00 C+0
ATOM 13 O 0 -1.541 -1.459 -3.070 0.00 0.00 O+0
ATOM 14 H 0 -0.264 -1.492 -0.775 0.00 0.00 H+0
ATOM 15 O 0 -2.862 -2.189 0.680 0.00 0.00 O+0
ATOM 16 C 0 -4.895 0.666 -1.397 0.00 0.00 C+0
ATOM 17 C 0 -6.113 1.375 -0.784 0.00 0.00 C+0
ATOM 18 C 0 -6.805 0.381 0.177 0.00 0.00 C+0
ATOM 19 O 0 -5.999 -0.624 0.795 0.00 0.00 O+0
ATOM 20 C 0 -6.106 0.593 1.536 0.00 0.00 C+0
ATOM 21 C 0 -5.055 1.696 1.272 0.00 0.00 C+0
ATOM 22 C 0 -3.761 1.011 0.809 0.00 0.00 C+0
ATOM 23 N 0 -5.597 2.447 0.108 0.00 0.00 N+1
ATOM 24 C 0 -4.531 3.206 -0.559 0.00 0.00 C+0
ATOM 25 C 0 -3.972 4.255 0.405 0.00 0.00 C+0
ATOM 26 C 0 -2.862 5.046 -0.290 0.00 0.00 C+0
ATOM 27 C 0 -2.303 6.095 0.674 0.00 0.00 C+0
ATOM 28 C 0 -6.685 3.339 0.529 0.00 0.00 C+0
ATOM 29 Br 0 14.489 1.142 0.058 0.00 0.00 Br-1
ATOM 30 H 0 1.223 -2.641 0.558 0.00 0.00 H+0
ATOM 31 H 0 1.871 -4.631 1.853 0.00 0.00 H+0
ATOM 32 H 0 0.351 -6.565 1.982 0.00 0.00 H+0
ATOM 33 H 0 -1.816 -6.507 0.816 0.00 0.00 H+0
ATOM 34 H 0 -2.462 -4.519 -0.485 0.00 0.00 H+0
ATOM 35 H 0 -0.387 -3.127 -2.679 0.00 0.00 H+0
ATOM 36 H 0 -2.130 -3.309 -2.365 0.00 0.00 H+0
ATOM 37 H 0 -1.675 -1.750 -3.983 0.00 0.00 H+0
ATOM 38 H 0 -4.262 1.397 -1.900 0.00 0.00 H+0
ATOM 39 H 0 -5.231 -0.084 -2.113 0.00 0.00 H+0
ATOM 40 H 0 -6.794 1.753 -1.546 0.00 0.00 H+0
ATOM 41 H 0 -7.879 0.227 0.067 0.00 0.00 H+0
ATOM 42 H 0 -6.649 0.610 2.481 0.00 0.00 H+0
ATOM 43 H 0 -4.895 2.330 2.145 0.00 0.00 H+0
ATOM 44 H 0 -3.293 0.505 1.653 0.00 0.00 H+0
ATOM 45 H 0 -3.077 1.757 0.404 0.00 0.00 H+0
ATOM 46 H 0 -3.733 2.527 -0.859 0.00 0.00 H+0
ATOM 47 H 0 -4.936 3.703 -1.441 0.00 0.00 H+0
ATOM 48 H 0 -4.770 4.935 0.705 0.00 0.00 H+0
ATOM 49 H 0 -3.567 3.759 1.287 0.00 0.00 H+0
ATOM 50 H 0 -2.065 4.367 -0.590 0.00 0.00 H+0
ATOM 51 H 0 -3.267 5.543 -1.172 0.00 0.00 H+0
ATOM 52 H 0 -3.101 6.775 0.974 0.00 0.00 H+0
ATOM 53 H 0 -1.898 5.598 1.556 0.00 0.00 H+0
ATOM 54 H 0 -1.513 6.659 0.179 0.00 0.00 H+0
ATOM 55 H 0 -6.308 4.051 1.263 0.00 0.00 H+0
ATOM 56 H 0 -7.068 3.879 -0.337 0.00 0.00 H+0
ATOM 57 H 0 -7.487 2.749 0.973 0.00 0.00 H+0
CONECT 2 1 22 3 16 NONE 62
CONECT 3 2 4 0 0 NONE 63
CONECT 4 3 5 15 0 NONE 64
CONECT 5 4 6 12 14 NONE 65
CONECT 6 5 11 7 0 NONE 66
CONECT 7 6 8 30 0 NONE 67
CONECT 8 7 9 31 0 NONE 68
CONECT 9 8 10 32 0 NONE 69
CONECT 10 9 11 33 0 NONE 70
CONECT 11 10 6 34 0 NONE 71
CONECT 12 5 13 35 36 NONE 72
CONECT 13 12 37 0 0 NONE 73
CONECT 15 4 0 0 0 NONE 74
CONECT 16 2 17 38 39 NONE 75
CONECT 17 16 23 18 40 NONE 76
CONECT 18 17 20 19 41 NONE 77
CONECT 19 18 20 0 0 NONE 78
CONECT 20 19 18 21 42 NONE 79
CONECT 21 20 22 23 43 NONE 80
CONECT 22 21 2 44 45 NONE 81
CONECT 23 21 17 24 28 NONE 82
CONECT 24 23 25 46 47 NONE 83
CONECT 25 24 26 48 49 NONE 84
CONECT 26 25 27 50 51 NONE 85
CONECT 27 26 52 53 54 NONE 86
CONECT 28 23 55 56 57 NONE 87
END NONE 88</inlineContents>
</jmolApplet>
</jmol>

Above: 3D structure of Hyoscine-N-Butylbromide

This derivative is used to treat bowel diseases. Like Hysocine, this drug can relax the muscle lining of the gastrointestinal and urinary tracts, to reduce spasms and involuntary movements.

==History of Hycocine==

Before the discovery of the various anesthetic agents people underwent severe pain and agony. Patients were strapped down or were given alcohol and other sedative drugs to ameliorate the pain of surgery.

Despite hycocine's high toxicity, at suitable doses this substance has beneficial medicinal effects, which were recognized in folk medicine throughout the world, and later on in scientific medicine.

Hycocine is a popular poison used in classic literature, due to it's presence in a number of plants. Its toxic properties, regardless of whether it is administered internally or externally, makes it a highly useful drug for
physicians and poisoners alike!

Hyoscine in the form of nightshade was also used by practitioners of witchcraft in the concocting of flying potions – large amounts
of it caused hallucination and a sensation of floating.

Scopolamine was first isolated by Albert Ladenburg, in the late 1800's. He isolated it as a racemic mixture with Hyoscine.

[[Image:Racemic_mixture.GIF]]

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 C 0 3.453 2.304 0.685 0.00 0.00 C+0
ATOM 2 N 0 2.834 1.011 0.364 0.00 0.00 N+0
ATOM 3 C 0 3.140 0.731 -1.050 0.00 0.00 C+0
ATOM 4 C 0 4.049 -0.415 -0.670 0.00 0.00 C+0
ATOM 5 C 0 3.779 -0.036 0.796 0.00 0.00 C+0
ATOM 6 C 0 3.013 -1.211 1.448 0.00 0.00 C+0
ATOM 7 C 0 1.803 -1.504 0.547 0.00 0.00 C+0
ATOM 8 O 0 0.905 -0.362 0.569 0.00 0.00 O+0
ATOM 9 C 0 -0.415 -0.542 0.402 0.00 0.00 C+0
ATOM 10 C 0 -1.346 0.642 0.425 0.00 0.00 C+0
ATOM 11 H 0 -1.269 1.147 1.388 0.00 0.00 H+0
ATOM 12 C 0 -2.762 0.172 0.217 0.00 0.00 C+0
ATOM 13 C 0 -3.720 0.412 1.184 0.00 0.00 C+0
ATOM 14 C 0 -5.019 -0.020 0.993 0.00 0.00 C+0
ATOM 15 C 0 -5.361 -0.691 -0.166 0.00 0.00 C+0
ATOM 16 C 0 -4.404 -0.930 -1.134 0.00 0.00 C+0
ATOM 17 C 0 -3.105 -0.495 -0.945 0.00 0.00 C+0
ATOM 18 C 0 -0.962 1.615 -0.693 0.00 0.00 C+0
ATOM 19 O 0 -1.769 2.790 -0.599 0.00 0.00 O+0
ATOM 20 O 0 -0.856 -1.654 0.234 0.00 0.00 O+0
ATOM 21 C 0 2.236 -1.777 -0.892 0.00 0.00 C+0
ATOM 22 O 0 2.879 -0.629 -1.443 0.00 0.00 O+0
ATOM 23 H 0 3.037 3.076 0.039 0.00 0.00 H+0
ATOM 24 H 0 3.253 2.554 1.727 0.00 0.00 H+0
ATOM 25 H 0 4.530 2.240 0.527 0.00 0.00 H+0
ATOM 26 H 0 3.229 1.522 -1.779 0.00 0.00 H+0
ATOM 27 H 0 5.025 -0.717 -1.017 0.00 0.00 H+0
ATOM 28 H 0 4.633 0.313 1.349 0.00 0.00 H+0
ATOM 29 H 0 3.649 -2.091 1.502 0.00 0.00 H+0
ATOM 30 H 0 2.669 -0.932 2.441 0.00 0.00 H+0
ATOM 31 H 0 1.277 -2.379 0.934 0.00 0.00 H+0
ATOM 32 H 0 -3.453 0.936 2.090 0.00 0.00 H+0
ATOM 33 H 0 -5.767 0.167 1.750 0.00 0.00 H+0
ATOM 34 H 0 -6.376 -1.029 -0.315 0.00 0.00 H+0
ATOM 35 H 0 -4.671 -1.455 -2.039 0.00 0.00 H+0
ATOM 36 H 0 -2.357 -0.682 -1.701 0.00 0.00 H+0
ATOM 37 H 0 0.089 1.886 -0.593 0.00 0.00 H+0
ATOM 38 H 0 -1.124 1.139 -1.660 0.00 0.00 H+0
ATOM 39 H 0 -1.495 3.375 -1.319 0.00 0.00 H+0
ATOM 40 H 0 2.928 -2.620 -0.907 0.00 0.00 H+0
ATOM 41 H 0 1.358 -2.021 -1.492 0.00 0.00 H+0
CONECT 1 2 23 24 25 NONE 46
CONECT 2 1 5 3 0 NONE 47
CONECT 3 2 22 4 26 NONE 48
CONECT 4 3 22 5 27 NONE 49
CONECT 5 4 2 6 28 NONE 50
CONECT 6 5 7 29 30 NONE 51
CONECT 7 6 8 21 31 NONE 52
CONECT 8 7 9 0 0 NONE 53
CONECT 9 8 10 20 0 NONE 54
CONECT 10 9 11 12 18 NONE 55
CONECT 12 10 17 13 0 NONE 56
CONECT 13 12 14 32 0 NONE 57
CONECT 14 13 15 33 0 NONE 58
CONECT 15 14 16 34 0 NONE 59
CONECT 16 15 17 35 0 NONE 60
CONECT 17 16 12 36 0 NONE 61
CONECT 18 10 19 37 38 NONE 62
CONECT 19 18 39 0 0 NONE 63
CONECT 20 9 0 0 0 NONE 64
CONECT 21 7 22 40 41 NONE 65
CONECT 22 21 3 4 0 NONE 66
END NONE 67
</inlineContents>
</jmolApplet>
</jmol>

Above: 3d structure of (+)-scopolamine

This was discovered when Ladenburg was crystalising hyoscyamine from exctracts of the plant Hyoseyamus and found that an alkaloid still remained in the solution. This alkaloid had never previously been isolated and up to this day was considered to be a waste product by scientists.

[[Image:Hyoseyamus.jpg]] Hyoseyamus (Ref 3)

To completely isolate the molecule, further purification was required, by further recrystallisation. Ladenburg also found that hyoscine decomposed to a froth at 196 to 198<sup>o</sup>C

=Recent history=
In August 2006 a chemical company from Queensland, Australia was being investigated by the Australian Federal Police over fears that a 100-kilogram shipment of hyoscine was diverted to Iraq. Documents from 2002 showed that the federal police questioned the company, Alkaloids of Australia, about a shipment of hyoscine, that was sent to the Syrian pharmaceutical company Ibn Hayan in 2001. US and British military reports show that hyoscine can also be used an "incapacitating agent", causing severe symptoms such as impaired vision, temporary delirium and an abnormally rapid heartbeat. Reports by the US Army show that an injection of as little as 1.5 milligrams of scopolamine hydrobromide can cause a soldier to become delirious for two to four hours. (Ref 4)

==References==

1. http://www.prevent-motion-sickness-scopolamine.com/

2. Savary, B. J. and D. K. Dougall. "Scopolamine Radioimmunoassay for Tissue- cultures of Datura." Phytochemistry 29.5 (1990): 1567-69.

3. http://ag.msu.montana.edu/cipm/cipmpics.asp?type=thumb&flag=1&id=144

4. http://www.theage.com.au/news/investigations/probe-over-nerve-gas-suspicion/2006/08/20/1156012411533.html

5. E. Leete et. al. "Use of Carbon- 13 Nuclear Magnetic Resonance to establish that the biosynthesis of tropic acid involves an intramolecular rearrangement of phenylalanine." Journal of the American Chemical Society, 1975

*[http://www.plantcell.org/cgi/reprint/7/7/1059.pdf/ Alkaloid Synthesis]- Tropane and Nicotine Alkaloids

6. http://www.drugdelivery.ca/s3557-s-HYOSCINE.aspx

7. http://www.hopepharm.com/motion/index.html

8. http://www.linnea-worldwide.com/products/hyoscine.asp

It:Hycocine

2006-10-26T15:40:33Z

Vl105: /* Hyoscine derivative: '''Hyoscine-N-Butylbromide''' */

== '''HYOSCINE''' ==

{| 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 that 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>
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<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 it 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. They studied the accumulation of scopolamine in cell and tissue cultures of Datura as a way of seeing on a biochemical level how the natural products scopolamine and hyoscyamine accumulate in plants of the Datura family. (Ref 2)

[[Image:Datura.jpg|thumb|''Datura wrightii'' ]] ''Datura wrightii''

Scopolamine can be isolated from plants by extraction:

[[Image:Biosynthesis_of_alkaloids2.GIF]] [http://www.plantcell.org/cgi/reprint/7/7/1059.pdf]

==Physical properties of Hycocine==

{| border="1"

|-
! Formula
| C1<sub>7</sub>H<sub>21</sub>NO<sub>4</sub>
|-
! Molecular weight
| 303.35
|-
! Melting point
| 59<sup>o</sup>C
|-
! Appearance
| white, amophous, semi-solid
|}

==Chemical Properties of Hycocine==

It is a drug that acts on the autonomic nervous system and prevents muscle spasm.
It is an alkaloid, obtained from various plants of the nightshade family (such as belladonna). [http://www.tiscali.co.uk/reference/encyclopaedia/hutchinson/m0014386.html]

The depressive action hycocine on the central nervous system makes it suitable for use in very tiny amounts in the treatment of
anxiety-related problems and travel-sickness (in the form of hyoscine hydrobromide, which is a type of anticholinergic drug).

In larger doses, it breaks down a person’s ability to discriminate and make reasoned judgment, making it a potential 'truth drug'.

==Effects of Hycocine==

It is frequently included in premedication to dry up lung secretions and as a postoperative sedative. It is also used to
treat ulcers, to relax the womb in labour, for travel sickness, and to dilate the pupils before an eye examination.

Hyoscine produces sedation. With higher doses it produces agitation and disorientation similar to that of atropine. Hyoscine also has a significant anti-emetic effect, and that is why it is used for the treatment of motion sickness (Rang et al., 1995)

Hyoscine induced a moderate bradycardia and a marked decrease in salivation when administered via injection. These
effects were maximal at 1 to 2 hours after administration of hyoscine but were no longer present at 4 hours.

Consistent behavioral effects of hyoscine in various experiments were a decrease in spontaneous speech and movement and a significant
decrease in energy.

When administered medically, hyoscine may cause the muscles in the eye to become relaxed, widening the pupil. Pupils may remain wide and not respond to light. They'll also be more sensitive.

Fatal doses of hyoscine causes the heart to cease functioning, which results in death.

There are side effects that are known to have affected patients (ref 6). The drug Hyoscine affects the autonomic nervous system so this could be the cause of those side effects:

* Dizziness
* Blurred vision
* Dry mouth
* Vomiting
* Irritation of the skin
* Problems in urinating

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''(+)-scopolamine'''
|-
! CAS Registry Number
| 51-34-3, 138-12-5, 64069-63-2, 124917-17-5
|-
! Chemical Name
|3-hydroxy-2-phenyl-propionic acid 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yl ester
|-
! Molecular Formula
| C17H21NO4
|-
! Molecular Weight
| 303.36
|-
|}

==Synthesis==

In 1957 Fodor synthesised scopolamine via 2 steps. He found that the first work up step to produce 3α-acetoxytrop-6-ene, could be done in three different ways.

[[Image:Route1-2.gif]]

[[Image:route3.gif]]

This shows how the enantiomer of hyoscine is made:

[[image:Synthesis_Scopolamine.gif]] [http://www.ucalgary.ca/~bali/chem353/project/00final/00final.htm#chemistry]

==NMR Spectrum==

'''C-NMR'''

[[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
|-
|}

'''H-NMR'''

[[image:H-NMR_Scopolamine.gif]] [http://www.ucalgary.ca/~bali/chem353/project/00final/00final.htm#chemistry]

==Uses of Hycocine==

Scopolamine is the main ingredient in skin patches marketed as "Tranderm Scop" [[1]], which are skin patches that can prevent nausea and vomitting caused by motion sickness.

The drug scopolamine is sold under the brand name of Scopace®. It is marketed to help prevent nausea and vomiting often caused by motion sickness. For this purpose it is sold over the counter but some doctors may use it to help ease the symptoms of irritable bowel, intestinal problems, parkinsonism, spastic muscle states, divertisulitis, to name a few.
[[Image:Scopace.GIF|thumb|Description]]

==Hyoscine derivative: '''Hyoscine-N-Butylbromide'''==

There is a derivative of Hyoscine called: '''Hyoscine-N-Butylbromide'''. This compound derivative can be obtained from the leaves of the Duboisia tree in Australia (ref 8).

[[Image:vlrawleaves.gif]]
Raw Duboisia leaves

[[Image:vlduboisiatree.jpg]]
Duboisia tree shrubs

The structure of this derivative:
[[Image:vlhyoscinederivative.gif]]

<jmol>
<jmolApplet>
<size>400</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>ATOM 1 H 0 -4.700 -0.815 0.156 0.00 0.00 H+0
ATOM 2 C 0 -4.102 -0.014 -0.277 0.00 0.00 C+0
ATOM 3 O 0 -2.875 -0.567 -0.821 0.00 0.00 O+0
ATOM 4 C 0 -2.330 -1.663 -0.270 0.00 0.00 C+0
ATOM 5 C 0 -1.057 -2.238 -0.834 0.00 0.00 C+0
ATOM 6 C 0 -0.660 -3.456 -0.041 0.00 0.00 C+0
ATOM 7 C 0 0.556 -3.488 0.614 0.00 0.00 C+0
ATOM 8 C 0 0.920 -4.606 1.342 0.00 0.00 C+0
ATOM 9 C 0 0.067 -5.691 1.414 0.00 0.00 C+0
ATOM 10 C 0 -1.150 -5.659 0.760 0.00 0.00 C+0
ATOM 11 C 0 -1.511 -4.544 0.026 0.00 0.00 C+0
ATOM 12 C 0 -1.279 -2.631 -2.296 0.00 0.00 C+0
ATOM 13 O 0 -1.541 -1.459 -3.070 0.00 0.00 O+0
ATOM 14 H 0 -0.264 -1.492 -0.775 0.00 0.00 H+0
ATOM 15 O 0 -2.862 -2.189 0.680 0.00 0.00 O+0
ATOM 16 C 0 -4.895 0.666 -1.397 0.00 0.00 C+0
ATOM 17 C 0 -6.113 1.375 -0.784 0.00 0.00 C+0
ATOM 18 C 0 -6.805 0.381 0.177 0.00 0.00 C+0
ATOM 19 O 0 -5.999 -0.624 0.795 0.00 0.00 O+0
ATOM 20 C 0 -6.106 0.593 1.536 0.00 0.00 C+0
ATOM 21 C 0 -5.055 1.696 1.272 0.00 0.00 C+0
ATOM 22 C 0 -3.761 1.011 0.809 0.00 0.00 C+0
ATOM 23 N 0 -5.597 2.447 0.108 0.00 0.00 N+1
ATOM 24 C 0 -4.531 3.206 -0.559 0.00 0.00 C+0
ATOM 25 C 0 -3.972 4.255 0.405 0.00 0.00 C+0
ATOM 26 C 0 -2.862 5.046 -0.290 0.00 0.00 C+0
ATOM 27 C 0 -2.303 6.095 0.674 0.00 0.00 C+0
ATOM 28 C 0 -6.685 3.339 0.529 0.00 0.00 C+0
ATOM 29 Br 0 14.489 1.142 0.058 0.00 0.00 Br-1
ATOM 30 H 0 1.223 -2.641 0.558 0.00 0.00 H+0
ATOM 31 H 0 1.871 -4.631 1.853 0.00 0.00 H+0
ATOM 32 H 0 0.351 -6.565 1.982 0.00 0.00 H+0
ATOM 33 H 0 -1.816 -6.507 0.816 0.00 0.00 H+0
ATOM 34 H 0 -2.462 -4.519 -0.485 0.00 0.00 H+0
ATOM 35 H 0 -0.387 -3.127 -2.679 0.00 0.00 H+0
ATOM 36 H 0 -2.130 -3.309 -2.365 0.00 0.00 H+0
ATOM 37 H 0 -1.675 -1.750 -3.983 0.00 0.00 H+0
ATOM 38 H 0 -4.262 1.397 -1.900 0.00 0.00 H+0
ATOM 39 H 0 -5.231 -0.084 -2.113 0.00 0.00 H+0
ATOM 40 H 0 -6.794 1.753 -1.546 0.00 0.00 H+0
ATOM 41 H 0 -7.879 0.227 0.067 0.00 0.00 H+0
ATOM 42 H 0 -6.649 0.610 2.481 0.00 0.00 H+0
ATOM 43 H 0 -4.895 2.330 2.145 0.00 0.00 H+0
ATOM 44 H 0 -3.293 0.505 1.653 0.00 0.00 H+0
ATOM 45 H 0 -3.077 1.757 0.404 0.00 0.00 H+0
ATOM 46 H 0 -3.733 2.527 -0.859 0.00 0.00 H+0
ATOM 47 H 0 -4.936 3.703 -1.441 0.00 0.00 H+0
ATOM 48 H 0 -4.770 4.935 0.705 0.00 0.00 H+0
ATOM 49 H 0 -3.567 3.759 1.287 0.00 0.00 H+0
ATOM 50 H 0 -2.065 4.367 -0.590 0.00 0.00 H+0
ATOM 51 H 0 -3.267 5.543 -1.172 0.00 0.00 H+0
ATOM 52 H 0 -3.101 6.775 0.974 0.00 0.00 H+0
ATOM 53 H 0 -1.898 5.598 1.556 0.00 0.00 H+0
ATOM 54 H 0 -1.513 6.659 0.179 0.00 0.00 H+0
ATOM 55 H 0 -6.308 4.051 1.263 0.00 0.00 H+0
ATOM 56 H 0 -7.068 3.879 -0.337 0.00 0.00 H+0
ATOM 57 H 0 -7.487 2.749 0.973 0.00 0.00 H+0
CONECT 2 1 22 3 16 NONE 62
CONECT 3 2 4 0 0 NONE 63
CONECT 4 3 5 15 0 NONE 64
CONECT 5 4 6 12 14 NONE 65
CONECT 6 5 11 7 0 NONE 66
CONECT 7 6 8 30 0 NONE 67
CONECT 8 7 9 31 0 NONE 68
CONECT 9 8 10 32 0 NONE 69
CONECT 10 9 11 33 0 NONE 70
CONECT 11 10 6 34 0 NONE 71
CONECT 12 5 13 35 36 NONE 72
CONECT 13 12 37 0 0 NONE 73
CONECT 15 4 0 0 0 NONE 74
CONECT 16 2 17 38 39 NONE 75
CONECT 17 16 23 18 40 NONE 76
CONECT 18 17 20 19 41 NONE 77
CONECT 19 18 20 0 0 NONE 78
CONECT 20 19 18 21 42 NONE 79
CONECT 21 20 22 23 43 NONE 80
CONECT 22 21 2 44 45 NONE 81
CONECT 23 21 17 24 28 NONE 82
CONECT 24 23 25 46 47 NONE 83
CONECT 25 24 26 48 49 NONE 84
CONECT 26 25 27 50 51 NONE 85
CONECT 27 26 52 53 54 NONE 86
CONECT 28 23 55 56 57 NONE 87
END NONE 88</inlineContents>
</jmolApplet>
</jmol>

Above: 3D structure of Hyoscine-N-Butylbromide

This derivative is used to treat bowel diseases. Like Hysocine, this drug can relax the muscle lining of the gastrointestinal and urinary tracts, to reduce spasms and involuntary movements.

==History of Hycocine==

Before the discovery of the various anesthetic agents people underwent severe pain and agony. Patients were strapped down or were given alcohol and other sedative drugs to ameliorate the pain of surgery.

Despite hycocine's high toxicity, at suitable doses this substance has beneficial medicinal effects, which were recognized in folk medicine throughout the world, and later on in scientific medicine.

Hycocine is a popular poison used in classic literature, due to it's presence in a number of plants. Its toxic properties, regardless of whether it is administered internally or externally, makes it a highly useful drug for
physicians and poisoners alike!

Hyoscine in the form of nightshade was also used by practitioners of witchcraft in the concocting of flying potions – large amounts
of it caused hallucination and a sensation of floating.

Scopolamine was first isolated by Albert Ladenburg, in the late 1800's. He isolated it as a racemic mixture with Hyoscine.

[[Image:Racemic_mixture.GIF]]

This was discovered when Ladenburg was crystalising hyoscyamine from exctracts of the plant Hyoseyamus and found that an alkaloid still remained in the solution. This alkaloid had never previously been isolated and up to this day was considered to be a waste product by scientists.

[[Image:Hyoseyamus.jpg]] Hyoseyamus (Ref 3)

To completely isolate the molecule, further purification was required, by further recrystallisation. Ladenburg also found that hyoscine decomposed to a froth at 196 to 198<sup>o</sup>C

=Recent history=
In August 2006 a chemical company from Queensland, Australia was being investigated by the Australian Federal Police over fears that a 100-kilogram shipment of hyoscine was diverted to Iraq. Documents from 2002 showed that the federal police questioned the company, Alkaloids of Australia, about a shipment of hyoscine, that was sent to the Syrian pharmaceutical company Ibn Hayan in 2001. US and British military reports show that hyoscine can also be used an "incapacitating agent", causing severe symptoms such as impaired vision, temporary delirium and an abnormally rapid heartbeat. Reports by the US Army show that an injection of as little as 1.5 milligrams of scopolamine hydrobromide can cause a soldier to become delirious for two to four hours. (Ref 4)

==References==

1. http://www.prevent-motion-sickness-scopolamine.com/

2. Savary, B. J. and D. K. Dougall. "Scopolamine Radioimmunoassay for Tissue- cultures of Datura." Phytochemistry 29.5 (1990): 1567-69.

3. http://ag.msu.montana.edu/cipm/cipmpics.asp?type=thumb&flag=1&id=144

4. http://www.theage.com.au/news/investigations/probe-over-nerve-gas-suspicion/2006/08/20/1156012411533.html

5. E. Leete et. al. "Use of Carbon- 13 Nuclear Magnetic Resonance to establish that the biosynthesis of tropic acid involves an intramolecular rearrangement of phenylalanine." Journal of the American Chemical Society, 1975

*[http://www.plantcell.org/cgi/reprint/7/7/1059.pdf/ Alkaloid Synthesis]- Tropane and Nicotine Alkaloids

6. http://www.drugdelivery.ca/s3557-s-HYOSCINE.aspx

7. http://www.hopepharm.com/motion/index.html

8. http://www.linnea-worldwide.com/products/hyoscine.asp

It:Hycocine

2006-10-26T15:35:09Z

Vl105: /* Hyoscine derivative: '''Hyoscine-N-Butylbromide''' */

== '''HYOSCINE''' ==

{| 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 that 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 it 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. They studied the accumulation of scopolamine in cell and tissue cultures of Datura as a way of seeing on a biochemical level how the natural products scopolamine and hyoscyamine accumulate in plants of the Datura family. (Ref 2)

[[Image:Datura.jpg|thumb|''Datura wrightii'' ]] ''Datura wrightii''

Scopolamine can be isolated from plants by extraction:

[[Image:Biosynthesis_of_alkaloids2.GIF]] [http://www.plantcell.org/cgi/reprint/7/7/1059.pdf]

==Physical properties of Hycocine==

{| border="1"

|-
! Formula
| C1<sub>7</sub>H<sub>21</sub>NO<sub>4</sub>
|-
! Molecular weight
| 303.35
|-
! Melting point
| 59<sup>o</sup>C
|-
! Appearance
| white, amophous, semi-solid
|}

==Chemical Properties of Hycocine==

It is a drug that acts on the autonomic nervous system and prevents muscle spasm.
It is an alkaloid, obtained from various plants of the nightshade family (such as belladonna). [http://www.tiscali.co.uk/reference/encyclopaedia/hutchinson/m0014386.html]

The depressive action hycocine on the central nervous system makes it suitable for use in very tiny amounts in the treatment of
anxiety-related problems and travel-sickness (in the form of hyoscine hydrobromide, which is a type of anticholinergic drug).

In larger doses, it breaks down a person’s ability to discriminate and make reasoned judgment, making it a potential 'truth drug'.

==Effects of Hycocine==

It is frequently included in premedication to dry up lung secretions and as a postoperative sedative. It is also used to
treat ulcers, to relax the womb in labour, for travel sickness, and to dilate the pupils before an eye examination.

Hyoscine produces sedation. With higher doses it produces agitation and disorientation similar to that of atropine. Hyoscine also has a significant anti-emetic effect, and that is why it is used for the treatment of motion sickness (Rang et al., 1995)

Hyoscine induced a moderate bradycardia and a marked decrease in salivation when administered via injection. These
effects were maximal at 1 to 2 hours after administration of hyoscine but were no longer present at 4 hours.

Consistent behavioral effects of hyoscine in various experiments were a decrease in spontaneous speech and movement and a significant
decrease in energy.

When administered medically, hyoscine may cause the muscles in the eye to become relaxed, widening the pupil. Pupils may remain wide and not respond to light. They'll also be more sensitive.

Fatal doses of hyoscine causes the heart to cease functioning, which results in death.

There are side effects that are known to have affected patients (ref 6). The drug Hyoscine affects the autonomic nervous system so this could be the cause of those side effects:

* Dizziness
* Blurred vision
* Dry mouth
* Vomiting
* Irritation of the skin
* Problems in urinating

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''(+)-scopolamine'''
|-
! CAS Registry Number
| 51-34-3, 138-12-5, 64069-63-2, 124917-17-5
|-
! Chemical Name
|3-hydroxy-2-phenyl-propionic acid 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yl ester
|-
! Molecular Formula
| C17H21NO4
|-
! Molecular Weight
| 303.36
|-
|}

==Synthesis==

In 1957 Fodor synthesised scopolamine via 2 steps. He found that the first work up step to produce 3α-acetoxytrop-6-ene, could be done in three different ways.

[[Image:Route1-2.gif]]

[[Image:route3.gif]]

This shows how the enantiomer of hyoscine is made:

[[image:Synthesis_Scopolamine.gif]] [http://www.ucalgary.ca/~bali/chem353/project/00final/00final.htm#chemistry]

==NMR Spectrum==

'''C-NMR'''

[[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
|-
|}

'''H-NMR'''

[[image:H-NMR_Scopolamine.gif]] [http://www.ucalgary.ca/~bali/chem353/project/00final/00final.htm#chemistry]

==Uses of Hycocine==

Scopolamine is the main ingredient in skin patches marketed as "Tranderm Scop" [[1]], which are skin patches that can prevent nausea and vomitting caused by motion sickness.

The drug scopolamine is sold under the brand name of Scopace®. It is marketed to help prevent nausea and vomiting often caused by motion sickness. For this purpose it is sold over the counter but some doctors may use it to help ease the symptoms of irritable bowel, intestinal problems, parkinsonism, spastic muscle states, divertisulitis, to name a few.
[[Image:Scopace.GIF|thumb|Description]]

==Hyoscine derivative: '''Hyoscine-N-Butylbromide'''==

There is a derivative of Hyoscine called: '''Hyoscine-N-Butylbromide'''. This compound derivative can be obtained from the leaves of the Duboisia tree in Australia (ref 8).

[[Image:vlrawleaves.gif]]
Raw Duboisia leaves

[[Image:vlduboisiatree.jpg]]
Duboisia tree shrubs

The structure of this derivative:
[[Image:vlhyoscinederivative.gif]]

<jmol>
<jmolApplet>
<size>400</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>ATOM 1 H 0 -4.700 -0.815 0.156 0.00 0.00 H+0
ATOM 2 C 0 -4.102 -0.014 -0.277 0.00 0.00 C+0
ATOM 3 O 0 -2.875 -0.567 -0.821 0.00 0.00 O+0
ATOM 4 C 0 -2.330 -1.663 -0.270 0.00 0.00 C+0
ATOM 5 C 0 -1.057 -2.238 -0.834 0.00 0.00 C+0
ATOM 6 C 0 -0.660 -3.456 -0.041 0.00 0.00 C+0
ATOM 7 C 0 0.556 -3.488 0.614 0.00 0.00 C+0
ATOM 8 C 0 0.920 -4.606 1.342 0.00 0.00 C+0
ATOM 9 C 0 0.067 -5.691 1.414 0.00 0.00 C+0
ATOM 10 C 0 -1.150 -5.659 0.760 0.00 0.00 C+0
ATOM 11 C 0 -1.511 -4.544 0.026 0.00 0.00 C+0
ATOM 12 C 0 -1.279 -2.631 -2.296 0.00 0.00 C+0
ATOM 13 O 0 -1.541 -1.459 -3.070 0.00 0.00 O+0
ATOM 14 H 0 -0.264 -1.492 -0.775 0.00 0.00 H+0
ATOM 15 O 0 -2.862 -2.189 0.680 0.00 0.00 O+0
ATOM 16 C 0 -4.895 0.666 -1.397 0.00 0.00 C+0
ATOM 17 C 0 -6.113 1.375 -0.784 0.00 0.00 C+0
ATOM 18 C 0 -6.805 0.381 0.177 0.00 0.00 C+0
ATOM 19 O 0 -5.999 -0.624 0.795 0.00 0.00 O+0
ATOM 20 C 0 -6.106 0.593 1.536 0.00 0.00 C+0
ATOM 21 C 0 -5.055 1.696 1.272 0.00 0.00 C+0
ATOM 22 C 0 -3.761 1.011 0.809 0.00 0.00 C+0
ATOM 23 N 0 -5.597 2.447 0.108 0.00 0.00 N+1
ATOM 24 C 0 -4.531 3.206 -0.559 0.00 0.00 C+0
ATOM 25 C 0 -3.972 4.255 0.405 0.00 0.00 C+0
ATOM 26 C 0 -2.862 5.046 -0.290 0.00 0.00 C+0
ATOM 27 C 0 -2.303 6.095 0.674 0.00 0.00 C+0
ATOM 28 C 0 -6.685 3.339 0.529 0.00 0.00 C+0
ATOM 29 Br 0 14.489 1.142 0.058 0.00 0.00 Br-1
ATOM 30 H 0 1.223 -2.641 0.558 0.00 0.00 H+0
ATOM 31 H 0 1.871 -4.631 1.853 0.00 0.00 H+0
ATOM 32 H 0 0.351 -6.565 1.982 0.00 0.00 H+0
ATOM 33 H 0 -1.816 -6.507 0.816 0.00 0.00 H+0
ATOM 34 H 0 -2.462 -4.519 -0.485 0.00 0.00 H+0
ATOM 35 H 0 -0.387 -3.127 -2.679 0.00 0.00 H+0
ATOM 36 H 0 -2.130 -3.309 -2.365 0.00 0.00 H+0
ATOM 37 H 0 -1.675 -1.750 -3.983 0.00 0.00 H+0
ATOM 38 H 0 -4.262 1.397 -1.900 0.00 0.00 H+0
ATOM 39 H 0 -5.231 -0.084 -2.113 0.00 0.00 H+0
ATOM 40 H 0 -6.794 1.753 -1.546 0.00 0.00 H+0
ATOM 41 H 0 -7.879 0.227 0.067 0.00 0.00 H+0
ATOM 42 H 0 -6.649 0.610 2.481 0.00 0.00 H+0
ATOM 43 H 0 -4.895 2.330 2.145 0.00 0.00 H+0
ATOM 44 H 0 -3.293 0.505 1.653 0.00 0.00 H+0
ATOM 45 H 0 -3.077 1.757 0.404 0.00 0.00 H+0
ATOM 46 H 0 -3.733 2.527 -0.859 0.00 0.00 H+0
ATOM 47 H 0 -4.936 3.703 -1.441 0.00 0.00 H+0
ATOM 48 H 0 -4.770 4.935 0.705 0.00 0.00 H+0
ATOM 49 H 0 -3.567 3.759 1.287 0.00 0.00 H+0
ATOM 50 H 0 -2.065 4.367 -0.590 0.00 0.00 H+0
ATOM 51 H 0 -3.267 5.543 -1.172 0.00 0.00 H+0
ATOM 52 H 0 -3.101 6.775 0.974 0.00 0.00 H+0
ATOM 53 H 0 -1.898 5.598 1.556 0.00 0.00 H+0
ATOM 54 H 0 -1.513 6.659 0.179 0.00 0.00 H+0
ATOM 55 H 0 -6.308 4.051 1.263 0.00 0.00 H+0
ATOM 56 H 0 -7.068 3.879 -0.337 0.00 0.00 H+0
ATOM 57 H 0 -7.487 2.749 0.973 0.00 0.00 H+0
CONECT 2 1 22 3 16 NONE 62
CONECT 3 2 4 0 0 NONE 63
CONECT 4 3 5 15 0 NONE 64
CONECT 5 4 6 12 14 NONE 65
CONECT 6 5 11 7 0 NONE 66
CONECT 7 6 8 30 0 NONE 67
CONECT 8 7 9 31 0 NONE 68
CONECT 9 8 10 32 0 NONE 69
CONECT 10 9 11 33 0 NONE 70
CONECT 11 10 6 34 0 NONE 71
CONECT 12 5 13 35 36 NONE 72
CONECT 13 12 37 0 0 NONE 73
CONECT 15 4 0 0 0 NONE 74
CONECT 16 2 17 38 39 NONE 75
CONECT 17 16 23 18 40 NONE 76
CONECT 18 17 20 19 41 NONE 77
CONECT 19 18 20 0 0 NONE 78
CONECT 20 19 18 21 42 NONE 79
CONECT 21 20 22 23 43 NONE 80
CONECT 22 21 2 44 45 NONE 81
CONECT 23 21 17 24 28 NONE 82
CONECT 24 23 25 46 47 NONE 83
CONECT 25 24 26 48 49 NONE 84
CONECT 26 25 27 50 51 NONE 85
CONECT 27 26 52 53 54 NONE 86
CONECT 28 23 55 56 57 NONE 87
END NONE 88</inlineContents>
</jmolApplet>
</jmol>

This derivative is used to treat bowel diseases. Like Hysocine, this drug can relax the muscle lining of the gastrointestinal and urinary tracts, to reduce spasms and involuntary movements.

==History of Hycocine==

Before the discovery of the various anesthetic agents people underwent severe pain and agony. Patients were strapped down or were given alcohol and other sedative drugs to ameliorate the pain of surgery.

Despite hycocine's high toxicity, at suitable doses this substance has beneficial medicinal effects, which were recognized in folk medicine throughout the world, and later on in scientific medicine.

Hycocine is a popular poison used in classic literature, due to it's presence in a number of plants. Its toxic properties, regardless of whether it is administered internally or externally, makes it a highly useful drug for
physicians and poisoners alike!

Hyoscine in the form of nightshade was also used by practitioners of witchcraft in the concocting of flying potions – large amounts
of it caused hallucination and a sensation of floating.

Scopolamine was first isolated by Albert Ladenburg, in the late 1800's. He isolated it as a racemic mixture with Hyoscine.

[[Image:Racemic_mixture.GIF]]

This was discovered when Ladenburg was crystalising hyoscyamine from exctracts of the plant Hyoseyamus and found that an alkaloid still remained in the solution. This alkaloid had never previously been isolated and up to this day was considered to be a waste product by scientists.

[[Image:Hyoseyamus.jpg]] Hyoseyamus (Ref 3)

To completely isolate the molecule, further purification was required, by further recrystallisation. Ladenburg also found that hyoscine decomposed to a froth at 196 to 198<sup>o</sup>C

=Recent history=
In August 2006 a chemical company from Queensland, Australia was being investigated by the Australian Federal Police over fears that a 100-kilogram shipment of hyoscine was diverted to Iraq. Documents from 2002 showed that the federal police questioned the company, Alkaloids of Australia, about a shipment of hyoscine, that was sent to the Syrian pharmaceutical company Ibn Hayan in 2001. US and British military reports show that hyoscine can also be used an "incapacitating agent", causing severe symptoms such as impaired vision, temporary delirium and an abnormally rapid heartbeat. Reports by the US Army show that an injection of as little as 1.5 milligrams of scopolamine hydrobromide can cause a soldier to become delirious for two to four hours. (Ref 4)

==References==

1. http://www.prevent-motion-sickness-scopolamine.com/

2. Savary, B. J. and D. K. Dougall. "Scopolamine Radioimmunoassay for Tissue- cultures of Datura." Phytochemistry 29.5 (1990): 1567-69.

3. http://ag.msu.montana.edu/cipm/cipmpics.asp?type=thumb&flag=1&id=144

4. http://www.theage.com.au/news/investigations/probe-over-nerve-gas-suspicion/2006/08/20/1156012411533.html

5. E. Leete et. al. "Use of Carbon- 13 Nuclear Magnetic Resonance to establish that the biosynthesis of tropic acid involves an intramolecular rearrangement of phenylalanine." Journal of the American Chemical Society, 1975

*[http://www.plantcell.org/cgi/reprint/7/7/1059.pdf/ Alkaloid Synthesis]- Tropane and Nicotine Alkaloids

6. http://www.drugdelivery.ca/s3557-s-HYOSCINE.aspx

7. http://www.hopepharm.com/motion/index.html

8. http://www.linnea-worldwide.com/products/hyoscine.asp

It:Hycocine

2006-10-26T15:33:00Z

Vl105: /* Hyoscine derivative: '''Hyoscine-N-Butylbromide''' */

== '''HYOSCINE''' ==

{| 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 that 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>
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<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 it 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. They studied the accumulation of scopolamine in cell and tissue cultures of Datura as a way of seeing on a biochemical level how the natural products scopolamine and hyoscyamine accumulate in plants of the Datura family. (Ref 2)

[[Image:Datura.jpg|thumb|''Datura wrightii'' ]] ''Datura wrightii''

Scopolamine can be isolated from plants by extraction:

[[Image:Biosynthesis_of_alkaloids2.GIF]] [http://www.plantcell.org/cgi/reprint/7/7/1059.pdf]

==Physical properties of Hycocine==

{| border="1"

|-
! Formula
| C1<sub>7</sub>H<sub>21</sub>NO<sub>4</sub>
|-
! Molecular weight
| 303.35
|-
! Melting point
| 59<sup>o</sup>C
|-
! Appearance
| white, amophous, semi-solid
|}

==Chemical Properties of Hycocine==

It is a drug that acts on the autonomic nervous system and prevents muscle spasm.
It is an alkaloid, obtained from various plants of the nightshade family (such as belladonna). [http://www.tiscali.co.uk/reference/encyclopaedia/hutchinson/m0014386.html]

The depressive action hycocine on the central nervous system makes it suitable for use in very tiny amounts in the treatment of
anxiety-related problems and travel-sickness (in the form of hyoscine hydrobromide, which is a type of anticholinergic drug).

In larger doses, it breaks down a person’s ability to discriminate and make reasoned judgment, making it a potential 'truth drug'.

==Effects of Hycocine==

It is frequently included in premedication to dry up lung secretions and as a postoperative sedative. It is also used to
treat ulcers, to relax the womb in labour, for travel sickness, and to dilate the pupils before an eye examination.

Hyoscine produces sedation. With higher doses it produces agitation and disorientation similar to that of atropine. Hyoscine also has a significant anti-emetic effect, and that is why it is used for the treatment of motion sickness (Rang et al., 1995)

Hyoscine induced a moderate bradycardia and a marked decrease in salivation when administered via injection. These
effects were maximal at 1 to 2 hours after administration of hyoscine but were no longer present at 4 hours.

Consistent behavioral effects of hyoscine in various experiments were a decrease in spontaneous speech and movement and a significant
decrease in energy.

When administered medically, hyoscine may cause the muscles in the eye to become relaxed, widening the pupil. Pupils may remain wide and not respond to light. They'll also be more sensitive.

Fatal doses of hyoscine causes the heart to cease functioning, which results in death.

There are side effects that are known to have affected patients (ref 6). The drug Hyoscine affects the autonomic nervous system so this could be the cause of those side effects:

* Dizziness
* Blurred vision
* Dry mouth
* Vomiting
* Irritation of the skin
* Problems in urinating

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''(+)-scopolamine'''
|-
! CAS Registry Number
| 51-34-3, 138-12-5, 64069-63-2, 124917-17-5
|-
! Chemical Name
|3-hydroxy-2-phenyl-propionic acid 9-methyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yl ester
|-
! Molecular Formula
| C17H21NO4
|-
! Molecular Weight
| 303.36
|-
|}

==Synthesis==

In 1957 Fodor synthesised scopolamine via 2 steps. He found that the first work up step to produce 3α-acetoxytrop-6-ene, could be done in three different ways.

[[Image:Route1-2.gif]]

[[Image:route3.gif]]

This shows how the enantiomer of hyoscine is made:

[[image:Synthesis_Scopolamine.gif]] [http://www.ucalgary.ca/~bali/chem353/project/00final/00final.htm#chemistry]

==NMR Spectrum==

'''C-NMR'''

[[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
|-
|}

'''H-NMR'''

[[image:H-NMR_Scopolamine.gif]] [http://www.ucalgary.ca/~bali/chem353/project/00final/00final.htm#chemistry]

==Uses of Hycocine==

Scopolamine is the main ingredient in skin patches marketed as "Tranderm Scop" [[1]], which are skin patches that can prevent nausea and vomitting caused by motion sickness.

The drug scopolamine is sold under the brand name of Scopace®. It is marketed to help prevent nausea and vomiting often caused by motion sickness. For this purpose it is sold over the counter but some doctors may use it to help ease the symptoms of irritable bowel, intestinal problems, parkinsonism, spastic muscle states, divertisulitis, to name a few.
[[Image:Scopace.GIF|thumb|Description]]

==Hyoscine derivative: '''Hyoscine-N-Butylbromide'''==

There is a derivative of Hyoscine called: '''Hyoscine-N-Butylbromide'''. This compound derivative can be obtained from the leaves of the Duboisia tree in Australia (ref 8).

[[Image:vlrawleaves.gif]]
Raw Duboisia leaves

[[Image:vlduboisiatree.jpg]]
Duboisia tree shrubs

The structure of this derivative:
[[Image:vlhyoscinederivative.gif]]

<jmol>
<jmolApplet>
<size>200</size>
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<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>ATOM 1 H 0 -4.700 -0.815 0.156 0.00 0.00 H+0
ATOM 2 C 0 -4.102 -0.014 -0.277 0.00 0.00 C+0
ATOM 3 O 0 -2.875 -0.567 -0.821 0.00 0.00 O+0
ATOM 4 C 0 -2.330 -1.663 -0.270 0.00 0.00 C+0
ATOM 5 C 0 -1.057 -2.238 -0.834 0.00 0.00 C+0
ATOM 6 C 0 -0.660 -3.456 -0.041 0.00 0.00 C+0
ATOM 7 C 0 0.556 -3.488 0.614 0.00 0.00 C+0
ATOM 8 C 0 0.920 -4.606 1.342 0.00 0.00 C+0
ATOM 9 C 0 0.067 -5.691 1.414 0.00 0.00 C+0
ATOM 10 C 0 -1.150 -5.659 0.760 0.00 0.00 C+0
ATOM 11 C 0 -1.511 -4.544 0.026 0.00 0.00 C+0
ATOM 12 C 0 -1.279 -2.631 -2.296 0.00 0.00 C+0
ATOM 13 O 0 -1.541 -1.459 -3.070 0.00 0.00 O+0
ATOM 14 H 0 -0.264 -1.492 -0.775 0.00 0.00 H+0
ATOM 15 O 0 -2.862 -2.189 0.680 0.00 0.00 O+0
ATOM 16 C 0 -4.895 0.666 -1.397 0.00 0.00 C+0
ATOM 17 C 0 -6.113 1.375 -0.784 0.00 0.00 C+0
ATOM 18 C 0 -6.805 0.381 0.177 0.00 0.00 C+0
ATOM 19 O 0 -5.999 -0.624 0.795 0.00 0.00 O+0
ATOM 20 C 0 -6.106 0.593 1.536 0.00 0.00 C+0
ATOM 21 C 0 -5.055 1.696 1.272 0.00 0.00 C+0
ATOM 22 C 0 -3.761 1.011 0.809 0.00 0.00 C+0
ATOM 23 N 0 -5.597 2.447 0.108 0.00 0.00 N+1
ATOM 24 C 0 -4.531 3.206 -0.559 0.00 0.00 C+0
ATOM 25 C 0 -3.972 4.255 0.405 0.00 0.00 C+0
ATOM 26 C 0 -2.862 5.046 -0.290 0.00 0.00 C+0
ATOM 27 C 0 -2.303 6.095 0.674 0.00 0.00 C+0
ATOM 28 C 0 -6.685 3.339 0.529 0.00 0.00 C+0
ATOM 29 Br 0 14.489 1.142 0.058 0.00 0.00 Br-1
ATOM 30 H 0 1.223 -2.641 0.558 0.00 0.00 H+0
ATOM 31 H 0 1.871 -4.631 1.853 0.00 0.00 H+0
ATOM 32 H 0 0.351 -6.565 1.982 0.00 0.00 H+0
ATOM 33 H 0 -1.816 -6.507 0.816 0.00 0.00 H+0
ATOM 34 H 0 -2.462 -4.519 -0.485 0.00 0.00 H+0
ATOM 35 H 0 -0.387 -3.127 -2.679 0.00 0.00 H+0
ATOM 36 H 0 -2.130 -3.309 -2.365 0.00 0.00 H+0
ATOM 37 H 0 -1.675 -1.750 -3.983 0.00 0.00 H+0
ATOM 38 H 0 -4.262 1.397 -1.900 0.00 0.00 H+0
ATOM 39 H 0 -5.231 -0.084 -2.113 0.00 0.00 H+0
ATOM 40 H 0 -6.794 1.753 -1.546 0.00 0.00 H+0
ATOM 41 H 0 -7.879 0.227 0.067 0.00 0.00 H+0
ATOM 42 H 0 -6.649 0.610 2.481 0.00 0.00 H+0
ATOM 43 H 0 -4.895 2.330 2.145 0.00 0.00 H+0
ATOM 44 H 0 -3.293 0.505 1.653 0.00 0.00 H+0
ATOM 45 H 0 -3.077 1.757 0.404 0.00 0.00 H+0
ATOM 46 H 0 -3.733 2.527 -0.859 0.00 0.00 H+0
ATOM 47 H 0 -4.936 3.703 -1.441 0.00 0.00 H+0
ATOM 48 H 0 -4.770 4.935 0.705 0.00 0.00 H+0
ATOM 49 H 0 -3.567 3.759 1.287 0.00 0.00 H+0
ATOM 50 H 0 -2.065 4.367 -0.590 0.00 0.00 H+0
ATOM 51 H 0 -3.267 5.543 -1.172 0.00 0.00 H+0
ATOM 52 H 0 -3.101 6.775 0.974 0.00 0.00 H+0
ATOM 53 H 0 -1.898 5.598 1.556 0.00 0.00 H+0
ATOM 54 H 0 -1.513 6.659 0.179 0.00 0.00 H+0
ATOM 55 H 0 -6.308 4.051 1.263 0.00 0.00 H+0
ATOM 56 H 0 -7.068 3.879 -0.337 0.00 0.00 H+0
ATOM 57 H 0 -7.487 2.749 0.973 0.00 0.00 H+0
CONECT 2 1 22 3 16 NONE 62
CONECT 3 2 4 0 0 NONE 63
CONECT 4 3 5 15 0 NONE 64
CONECT 5 4 6 12 14 NONE 65
CONECT 6 5 11 7 0 NONE 66
CONECT 7 6 8 30 0 NONE 67
CONECT 8 7 9 31 0 NONE 68
CONECT 9 8 10 32 0 NONE 69
CONECT 10 9 11 33 0 NONE 70
CONECT 11 10 6 34 0 NONE 71
CONECT 12 5 13 35 36 NONE 72
CONECT 13 12 37 0 0 NONE 73
CONECT 15 4 0 0 0 NONE 74
CONECT 16 2 17 38 39 NONE 75
CONECT 17 16 23 18 40 NONE 76
CONECT 18 17 20 19 41 NONE 77
CONECT 19 18 20 0 0 NONE 78
CONECT 20 19 18 21 42 NONE 79
CONECT 21 20 22 23 43 NONE 80
CONECT 22 21 2 44 45 NONE 81
CONECT 23 21 17 24 28 NONE 82
CONECT 24 23 25 46 47 NONE 83
CONECT 25 24 26 48 49 NONE 84
CONECT 26 25 27 50 51 NONE 85
CONECT 27 26 52 53 54 NONE 86
CONECT 28 23 55 56 57 NONE 87
END NONE 88</inlineContents>
</jmolApplet>
</jmol>

This derivative is used to treat bowel diseases. Like Hysocine, this drug can relax the muscle lining of the gastrointestinal and urinary tracts, to reduce spasms and involuntary movements.

==History of Hycocine==

Before the discovery of the various anesthetic agents people underwent severe pain and agony. Patients were strapped down or were given alcohol and other sedative drugs to ameliorate the pain of surgery.

Despite hycocine's high toxicity, at suitable doses this substance has beneficial medicinal effects, which were recognized in folk medicine throughout the world, and later on in scientific medicine.

Hycocine is a popular poison used in classic literature, due to it's presence in a number of plants. Its toxic properties, regardless of whether it is administered internally or externally, makes it a highly useful drug for
physicians and poisoners alike!

Hyoscine in the form of nightshade was also used by practitioners of witchcraft in the concocting of flying potions – large amounts
of it caused hallucination and a sensation of floating.

Scopolamine was first isolated by Albert Ladenburg, in the late 1800's. He isolated it as a racemic mixture with Hyoscine.

[[Image:Racemic_mixture.GIF]]

This was discovered when Ladenburg was crystalising hyoscyamine from exctracts of the plant Hyoseyamus and found that an alkaloid still remained in the solution. This alkaloid had never previously been isolated and up to this day was considered to be a waste product by scientists.

[[Image:Hyoseyamus.jpg]] Hyoseyamus (Ref 3)

To completely isolate the molecule, further purification was required, by further recrystallisation. Ladenburg also found that hyoscine decomposed to a froth at 196 to 198<sup>o</sup>C

=Recent history=
In August 2006 a chemical company from Queensland, Australia was being investigated by the Australian Federal Police over fears that a 100-kilogram shipment of hyoscine was diverted to Iraq. Documents from 2002 showed that the federal police questioned the company, Alkaloids of Australia, about a shipment of hyoscine, that was sent to the Syrian pharmaceutical company Ibn Hayan in 2001. US and British military reports show that hyoscine can also be used an "incapacitating agent", causing severe symptoms such as impaired vision, temporary delirium and an abnormally rapid heartbeat. Reports by the US Army show that an injection of as little as 1.5 milligrams of scopolamine hydrobromide can cause a soldier to become delirious for two to four hours. (Ref 4)

==References==

1. http://www.prevent-motion-sickness-scopolamine.com/

2. Savary, B. J. and D. K. Dougall. "Scopolamine Radioimmunoassay for Tissue- cultures of Datura." Phytochemistry 29.5 (1990): 1567-69.

3. http://ag.msu.montana.edu/cipm/cipmpics.asp?type=thumb&flag=1&id=144

4. http://www.theage.com.au/news/investigations/probe-over-nerve-gas-suspicion/2006/08/20/1156012411533.html

5. E. Leete et. al. "Use of Carbon- 13 Nuclear Magnetic Resonance to establish that the biosynthesis of tropic acid involves an intramolecular rearrangement of phenylalanine." Journal of the American Chemical Society, 1975

*[http://www.plantcell.org/cgi/reprint/7/7/1059.pdf/ Alkaloid Synthesis]- Tropane and Nicotine Alkaloids

6. http://www.drugdelivery.ca/s3557-s-HYOSCINE.aspx

7. http://www.hopepharm.com/motion/index.html

8. http://www.linnea-worldwide.com/products/hyoscine.asp

It:Hycocine

2006-10-26T14:46:33Z

Vl105: /* Hyoscine derivative: Hyoscine-N-Butylbromide */

File:Vlhyoscinederivative.gif

2006-10-26T14:43:00Z

Vl105: structure of hyoscine derivative

structure of hyoscine derivative

It:Hycocine

2006-10-26T14:30:15Z

Vl105:

It:Hycocine

2006-10-26T14:26:35Z

Vl105:

It:Hycocine

2006-10-26T14:24:54Z

Vl105: added pictures of duboisia tree and leaves

It:Hycocine

2006-10-26T14:19:19Z

Vl105:

File:Vlduboisiatree.jpg

2006-10-26T14:18:21Z

Vl105: duboisia tree shrub

duboisia tree shrub

It:Hycocine

2006-10-26T14:17:51Z

Vl105: