ChemWiki - User contributions [en]

It:PhenylButazone

2006-12-07T13:32:47Z

Ss1305:

'''PhenylButazone'''

<jmol>
<jmolApplet>
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<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>phenylbutazone.mol
title1
title2
23 25 0 0 0 0 0 0 0 0999 V2000
0.1020 0.5214 -0.3987 N 0 0 0 0 0 0 0 0 0 1
-0.2149 -0.8923 -0.2482 N 0 0 0 0 0 0 0 0 0 2
1.4642 0.6456 -0.7455 C 0 0 0 0 0 0 0 0 0 3
0.9450 -1.6370 -0.5473 C 0 0 0 0 0 0 0 0 0 4
2.1019 -0.7189 -0.8165 C 0 0 0 0 0 0 0 0 0 5
-0.8166 1.5808 -0.0491 C 0 0 0 0 0 0 0 0 0 6
-1.5577 -1.3974 -0.0737 C 0 0 0 0 0 0 0 0 0 7
2.0074 1.7412 -0.9350 O 0 0 0 0 0 0 0 0 0 8
0.9581 -2.8731 -0.5869 O 0 0 0 0 0 0 0 0 0 9
3.1681 -0.9020 0.2757 C 0 0 0 0 0 0 0 0 0 10
-1.4410 1.5641 1.2038 C 0 0 0 0 0 0 0 0 0 11
-1.0742 2.6024 -0.9705 C 0 0 0 0 0 0 0 0 0 12
-2.5779 -0.9600 -0.9267 C 0 0 0 0 0 0 0 0 0 13
-1.8167 -2.3166 0.9492 C 0 0 0 0 0 0 0 0 0 14
4.4732 -0.1715 -0.0677 C 0 0 0 0 0 0 0 0 0 15
5.5029 -0.3629 1.0507 C 0 0 0 0 0 0 0 0 0 16
6.7974 0.3900 0.7252 C 0 0 0 0 0 0 0 0 0 17
-3.8691 -1.4469 -0.7463 C 0 0 0 0 0 0 0 0 0 18
-3.1119 -2.7966 1.1186 C 0 0 0 0 0 0 0 0 0 19
-1.9696 3.6123 -0.6312 C 0 0 0 0 0 0 0 0 0 20
-2.3350 2.5794 1.5306 C 0 0 0 0 0 0 0 0 0 21
-4.1363 -2.3629 0.2740 C 0 0 0 0 0 0 0 0 0 22
-2.5995 3.6012 0.6156 C 0 0 0 0 0 0 0 0 0 23
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22 19 2 0 0 0
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5 4 1 0 0 0
21 23 1 0 0 0
18 22 1 0 0 0
M END</inlineContents>
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''Medical applications''

Phenylbutazone has been used to treat serious pain in dogs due to osteoarthritis as it is a fast effective painkiller and also an anti-inflammatory. However dogs receiving intensive phenylbutazone therapy to tolerate the pain of osteoarthritis usually have regular blood work and renal monitoring to accompany this treatment. This is because an overdose of this drug is known to cause renal failure and liver injury.
This drug is also used to treat horses for such problems as musculoskeletal problems, soft tissue injury and bone and joint problems. Phenylbutazone is a nonsterodial drug which provides fast acting pain relief one to two hours after initial introduction into the body. The drug can be taken either orally or intravenously to the blood.

Safety

This drug is harmful of swallowed in excess of the dosage prescribed, it is also irritating to both the skin and eyes and respiratory system. Another precaution when dealing with phenylbutazone is that it should not be given to animals that are pregnant or nursing young as research has indicated it’s harmful to embryos and young.
This drug must not be injected into the muscles directly or under the skin.

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of phenylbutazone
|-
| align="center" colspan="5" bgcolor="#ffffff" | [[Image:Drawing.JPG|thumb|Description]]
|-
! {{chembox header}} colspan="5" |IR Spectrum of Phenylbutazone
|-
| align="center" colspan="5" bgcolor="#ffffff" | [[Image:MyIR.jpg|thumb|Description]]
|-
| align="center" colspan="5" bgcolor="#ffffff" |
|-
| [[Systematic Name]]
| colspan="2"| 4-butyl-1,2-diphenyl-pyrazolidine-3,5-dione
|-
| [[Alternative Chemical Names]]
| colspan="3"| Phenylbutazone
|-
| [[Chemical formula|Molecular formula]]
| colspan="2" | C<sub>19</sub>H<sub>20</sub>N<sub>2</sub>O<sub>2
|-
| [[Molecular Weight]]
| colspan="2" | 308.38
|-
| [[Melting Points]]
| colspan="2" | 104-107
|-
== Structure ==
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 1 1 1em 1em; border-collapse: collapse;"
|+ '''NMR of phenylbutazone'''
! [[Image:Nmr table.JPG|thumb|Description]] [[Image:Nmr pic.JPG|thumb|Description]] !!
<center><jmol>
|}</jmol>
|}

==References==
http://jpet.aspetjournals.org/cgi/reprint/266/1/81.pdf

www.chemexper.com/

http://www.wedgewoodpharmacy.com/monographs/phenylbutazone.asp

http://www.sciencemag.org/cgi/content/abstract/159/3822/1479

It:PhenylButazone

2006-12-07T13:31:58Z

Ss1305: /* References */

It:PhenylButazone

2006-12-07T13:31:43Z

Ss1305: /* References */

It:PhenylButazone

2006-12-07T13:30:56Z

Ss1305:

It:Gingerone

2006-10-26T14:23:26Z

Ss1305: /* Uses of Zingerone by Chemical Scientists */

{| 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

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

2006-10-26T14:23:14Z

Ss1305:

{| 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

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. (7)

==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

2006-10-26T14:22:52Z

Ss1305: /* References */

== '''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==

[[Image:vlrawleaves.gif]]

[[Image:vlduboisiatree.jpg]]

==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

It:Gingerone

2006-10-26T14:22:22Z

Ss1305:

{| 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

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. (7)

==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).

[[Further Abstract & Syntheses]]

2006-10-26T13:34:17Z

Ss1305:

Talk:It:Hycocine

2006-10-26T13:27:43Z

Ss1305:

I noticed that your structure was labelled Lignocaine when I assume it's supposed to be cytosine, so I changed the title. Hope that's right! If not you can change it back

I made the image that was uploaded named 'Biosynthesis_of_alkaloids' a bit smaller as I thought it was a bit big. I hope that this is ok with you.

Talk:It:Hycocine

2006-10-26T13:27:26Z

Ss1305:

I noticed that your structure was labelled Lignocaine when I assume it's supposed to be cytosine, so I changed the title. Hope that's right! If not you can change it back

I made the image that was uploaded named 'Biosynthesis_of_alkaloids' as I thought it was a bit big. I hope that this is ok with you.

It:Hycocine

2006-10-26T13:25:39Z

Ss1305: /* '''HYOSCINE''' */

== '''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)

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.

{| 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]]

==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

File:Hyoseyamus.jpg

2006-10-26T10:33:14Z

Ss1305:

It:Hycocine

2006-10-26T10:30:20Z

Ss1305:

== '''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)

==Physical properties of Hycoscine==

{| 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 Hyoscine==

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 Hyoscine==

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, hycocine 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.

{| 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==

[[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 Hyoscine==

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]]

==History of Hyoscine==

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.

==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.

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