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https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=5612
It:Morphine
2006-11-20T15:00:24Z
<p>Ffs05: edited synthesis image</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
== Properties of Morphine ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data''' <br />
|-<br />
| IUPAC Name<br />
| align="center"|7,8-didehydro-<br />
4,5-epoxy-17-methylmorphinan-3,6-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub><br />
|-<br />
| Molar Mass<br />
| align="center"|285.4 g/mol<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''<br />
|-<br />
| Bioavailability<br />
| align="center"|... ~30%<br />
|-<br />
| Protein binding<br />
| align="center"|... 30–40%<br />
|-<br />
| Metabolism<br />
| align="center"|... Hepatic 90%<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''<br />
|-<br />
| Pregnancy cat.<br />
| align="center"| C(AU) C(US)<br />
|-<br />
| Legal status<br />
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only<br />
|-<br />
| Dependence Liability<br />
| align="center"| Extremely High<br />
|-<br />
| Routes<br />
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
<br />
<br />
==Pharmacology of Morphine==<br />
<br />
Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:48:06 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 18.255 13.156 0.573 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.569 14.167 -0.163 1.00 0.00 <br />
ATOM 3 C3 MOL 1 16.417 14.732 0.663 1.00 0.00 <br />
ATOM 4 C4 MOL 1 18.496 15.366 -0.471 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.015 13.567 -1.482 1.00 0.00 <br />
ATOM 6 C6 MOL 1 15.693 15.779 0.018 1.00 0.00 <br />
ATOM 7 C7 MOL 1 15.307 13.777 1.020 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.942 15.313 2.010 1.00 0.00 <br />
ATOM 9 C9 MOL 1 17.646 16.451 -1.361 1.00 0.00 <br />
ATOM 10 N10 MOL 1 19.019 15.899 0.861 1.00 0.00 <br />
ATOM 11 C11 MOL 1 15.959 12.473 -1.196 1.00 0.00 <br />
ATOM 12 C12 MOL 1 14.403 15.799 0.518 1.00 0.00 <br />
ATOM 13 C13 MOL 1 16.179 16.645 -0.862 1.00 0.00 <br />
ATOM 14 O14 MOL 1 14.159 14.689 1.403 1.00 0.00 <br />
ATOM 15 C15 MOL 1 14.899 12.986 -0.210 1.00 0.00 <br />
ATOM 16 C16 MOL 1 17.969 16.420 1.747 1.00 0.00 <br />
ATOM 17 C17 MOL 1 20.056 16.927 0.663 1.00 0.00 <br />
ATOM 18 C18 MOL 1 13.566 16.775 0.184 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.281 17.721 -1.321 1.00 0.00 <br />
ATOM 20 O20 MOL 1 13.720 12.646 -0.346 1.00 0.00 <br />
ATOM 21 C21 MOL 1 21.259 16.286 0.008 1.00 0.00 <br />
ATOM 22 O22 MOL 1 12.278 16.816 0.702 1.00 0.00 <br />
ATOM 23 C23 MOL 1 14.040 17.798 -0.803 1.00 0.00 <br />
ATOM 24 C24 MOL 1 22.410 16.944 -0.094 1.00 0.00 <br />
ATOM 25 H25 MOL 1 19.357 15.031 -1.060 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:49:10 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 17.558 13.998 -0.496 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.076 15.115 0.248 1.00 0.00 <br />
ATOM 3 C3 MOL 1 17.258 16.394 -0.557 1.00 0.00 <br />
ATOM 4 C4 MOL 1 15.561 15.011 0.531 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.860 15.228 1.589 1.00 0.00 <br />
ATOM 6 C6 MOL 1 16.778 17.574 0.073 1.00 0.00 <br />
ATOM 7 C7 MOL 1 18.653 16.799 -0.879 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.508 16.294 -1.921 1.00 0.00 <br />
ATOM 9 C9 MOL 1 15.127 16.315 1.434 1.00 0.00 <br />
ATOM 10 N10 MOL 1 14.843 14.899 -0.812 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.354 15.543 1.336 1.00 0.00 <br />
ATOM 12 C12 MOL 1 17.493 18.660 -0.426 1.00 0.00 <br />
ATOM 13 C13 MOL 1 15.791 17.648 0.954 1.00 0.00 <br />
ATOM 14 O14 MOL 1 18.548 18.231 -1.333 1.00 0.00 <br />
ATOM 15 C15 MOL 1 19.467 16.754 0.400 1.00 0.00 <br />
ATOM 16 C16 MOL 1 15.014 16.064 -1.686 1.00 0.00 <br />
ATOM 17 C17 MOL 1 13.406 14.609 -0.651 1.00 0.00 <br />
ATOM 18 C18 MOL 1 17.129 19.900 -0.114 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.387 18.995 1.400 1.00 0.00 <br />
ATOM 20 O20 MOL 1 20.317 17.624 0.613 1.00 0.00 <br />
ATOM 21 C21 MOL 1 13.178 13.073 -0.836 1.00 0.00 <br />
ATOM 22 O22 MOL 1 17.801 20.995 -0.638 1.00 0.00 <br />
ATOM 23 C23 MOL 1 16.014 20.069 0.881 1.00 0.00 <br />
ATOM 24 C24 MOL 1 11.870 12.702 -0.129 1.00 0.00 <br />
ATOM 25 C25 MOL 1 13.234 12.318 0.500 1.00 0.00 <br />
ATOM 26 H26 MOL 1 19.132 16.101 -1.579 1.00 0.00 <br />
ATOM 27 H27 MOL 1 15.339 14.101 1.101 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Naloxone<br />
|Naltrexone<br />
|-<br />
|}<br />
<br />
<br />
<br />
Both naloxone and naltrexone are competitive antagonists at the μ- and κ-opioid receptors, and to a lesser extent at δ-opioid receptors. The blockade of these receptors is what prevents the opiods such as morphine, from combining with these receptor sites thus preventing the side effects usually caused by morphine.<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroin<br />
|-<br />
|align="left" colspan="3" bgcolor="white"| <br />
|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 14:36:05 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 12.755 17.484 0.278 1.00 0.00 <br />
ATOM 2 C2 MOL 1 14.165 17.279 0.259 1.00 0.00 <br />
ATOM 3 C3 MOL 1 14.598 16.294 -0.907 1.00 0.00 <br />
ATOM 4 C4 MOL 1 14.783 17.091 1.590 1.00 0.00 <br />
ATOM 5 C5 MOL 1 16.085 15.955 -0.655 1.00 0.00 <br />
ATOM 6 O6 MOL 1 13.944 14.927 -0.976 1.00 0.00 <br />
ATOM 7 C7 MOL 1 16.137 17.074 1.556 1.00 0.00 <br />
ATOM 8 C8 MOL 1 15.986 14.685 0.099 1.00 0.00 <br />
ATOM 9 C9 MOL 1 16.902 16.950 0.154 1.00 0.00 <br />
ATOM 10 C10 MOL 1 16.709 15.628 -2.040 1.00 0.00 <br />
ATOM 11 C11 MOL 1 14.759 14.077 -0.164 1.00 0.00 <br />
ATOM 12 C12 MOL 1 16.917 14.157 0.888 1.00 0.00 <br />
ATOM 13 C13 MOL 1 18.319 16.318 0.340 1.00 0.00 <br />
ATOM 14 C14 MOL 1 18.152 15.134 -1.868 1.00 0.00 <br />
ATOM 15 C15 MOL 1 14.483 12.853 0.325 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.177 14.972 1.210 1.00 0.00 <br />
ATOM 17 C17 MOL 1 16.666 12.844 1.470 1.00 0.00 <br />
ATOM 18 N18 MOL 1 18.922 16.087 -1.029 1.00 0.00 <br />
ATOM 19 O19 MOL 1 13.263 12.126 0.120 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.521 12.211 1.182 1.00 0.00 <br />
ATOM 21 C21 MOL 1 20.289 15.567 -0.871 1.00 0.00 <br />
ATOM 22 C22 MOL 1 12.251 12.761 -0.671 1.00 0.00 <br />
ATOM 23 H23 MOL 1 16.955 17.909 -0.379 1.00 0.00 <br />
ATOM 24 H24 MOL 1 14.357 16.925 -1.773 1.00 0.00 <br />
ATOM 25 H25 MOL 1 18.981 17.000 0.892 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 14:36:49 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.380 10.913 -0.058 1.00 0.00 <br />
ATOM 2 C2 MOL 1 22.712 10.864 -0.568 1.00 0.00 <br />
ATOM 3 C3 MOL 1 20.932 12.266 -0.071 1.00 0.00 <br />
ATOM 4 C4 MOL 1 23.445 9.558 -0.647 1.00 0.00 <br />
ATOM 5 O5 MOL 1 23.307 11.901 -0.901 1.00 0.00 <br />
ATOM 6 C6 MOL 1 19.783 12.581 0.994 1.00 0.00 <br />
ATOM 7 C7 MOL 1 20.757 12.864 -1.427 1.00 0.00 <br />
ATOM 8 C8 MOL 1 19.419 14.067 0.744 1.00 0.00 <br />
ATOM 9 O9 MOL 1 18.395 11.892 1.004 1.00 0.00 <br />
ATOM 10 C10 MOL 1 20.623 14.207 -1.407 1.00 0.00 <br />
ATOM 11 C11 MOL 1 18.168 13.977 -0.025 1.00 0.00 <br />
ATOM 12 C12 MOL 1 20.420 14.937 -0.012 1.00 0.00 <br />
ATOM 13 C13 MOL 1 19.051 14.641 2.138 1.00 0.00 <br />
ATOM 14 C14 MOL 1 17.546 12.770 0.237 1.00 0.00 <br />
ATOM 15 C15 MOL 1 17.644 14.930 -0.793 1.00 0.00 <br />
ATOM 16 C16 MOL 1 19.772 16.333 -0.179 1.00 0.00 <br />
ATOM 17 C17 MOL 1 18.538 16.078 2.002 1.00 0.00 <br />
ATOM 18 C18 MOL 1 16.298 12.542 -0.183 1.00 0.00 <br />
ATOM 19 C19 MOL 1 18.462 16.189 -1.090 1.00 0.00 <br />
ATOM 20 C20 MOL 1 16.318 14.720 -1.345 1.00 0.00 <br />
ATOM 21 N21 MOL 1 19.493 16.889 1.202 1.00 0.00 <br />
ATOM 22 O22 MOL 1 15.642 11.319 0.166 1.00 0.00 <br />
ATOM 23 C23 MOL 1 15.656 13.605 -1.022 1.00 0.00 <br />
ATOM 24 C24 MOL 1 18.950 18.247 1.075 1.00 0.00 <br />
ATOM 25 C25 MOL 1 14.263 11.150 -0.231 1.00 0.00 <br />
ATOM 26 C26 MOL 1 13.567 9.867 0.115 1.00 0.00 <br />
ATOM 27 O27 MOL 1 13.607 12.019 -0.820 1.00 0.00 <br />
ATOM 28 H28 MOL 1 21.358 14.995 0.556 1.00 0.00 <br />
ATOM 29 H29 MOL 1 20.362 12.366 1.900 1.00 0.00 <br />
ATOM 30 H30 MOL 1 20.458 17.021 -0.692 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br><br />
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br><br />
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.<br />
<br />
<br><br />
<br />
==Contraindications==<br />
<br />
*Acute Respiratory Depression <br />
*Acute Alcoholism <br />
*Acute pancreatitis (this may be a result of morphine use as well) <br />
*Renal failure (due to accumulation of the metabolite morphine-6-glucuronide) <br />
<br />
<br />
==Synthesis of Codeine from Morphine==<br />
<br />
[[Image:codeine_s.gif| Synthesis of Codeine]]<br />
<br><br />
<br />
<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]<br />
*Schmitz J, Stotts A, Rhoades H, Grabowski J. "Naltrexone and relapse prevention treatment for cocaine-dependent patients.". Addict Behav 26 (2): 167-80. PMID 11316375. <br />
*Chicago Recovery Alliance's naloxone distrobution project<br />
*Synthesis of codeine from morphine. Ai, Lin; Chen, Xiaoyuan; Zhang, Le. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005)</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=4806
It:Morphine
2006-11-02T13:00:41Z
<p>Ffs05: /* Synthesis of Codeine from Morphine */</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
== Properties of Morphine ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data''' <br />
|-<br />
| IUPAC Name<br />
| align="center"|7,8-didehydro-<br />
4,5-epoxy-17-methylmorphinan-3,6-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub><br />
|-<br />
| Molar Mass<br />
| align="center"|285.4 g/mol<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''<br />
|-<br />
| Bioavailability<br />
| align="center"|... ~30%<br />
|-<br />
| Protein binding<br />
| align="center"|... 30–40%<br />
|-<br />
| Metabolism<br />
| align="center"|... Hepatic 90%<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''<br />
|-<br />
| Pregnancy cat.<br />
| align="center"| C(AU) C(US)<br />
|-<br />
| Legal status<br />
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only<br />
|-<br />
| Dependence Liability<br />
| align="center"| Extremely High<br />
|-<br />
| Routes<br />
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
<br />
<br />
==Pharmacology of Morphine==<br />
<br />
Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:48:06 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 18.255 13.156 0.573 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.569 14.167 -0.163 1.00 0.00 <br />
ATOM 3 C3 MOL 1 16.417 14.732 0.663 1.00 0.00 <br />
ATOM 4 C4 MOL 1 18.496 15.366 -0.471 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.015 13.567 -1.482 1.00 0.00 <br />
ATOM 6 C6 MOL 1 15.693 15.779 0.018 1.00 0.00 <br />
ATOM 7 C7 MOL 1 15.307 13.777 1.020 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.942 15.313 2.010 1.00 0.00 <br />
ATOM 9 C9 MOL 1 17.646 16.451 -1.361 1.00 0.00 <br />
ATOM 10 N10 MOL 1 19.019 15.899 0.861 1.00 0.00 <br />
ATOM 11 C11 MOL 1 15.959 12.473 -1.196 1.00 0.00 <br />
ATOM 12 C12 MOL 1 14.403 15.799 0.518 1.00 0.00 <br />
ATOM 13 C13 MOL 1 16.179 16.645 -0.862 1.00 0.00 <br />
ATOM 14 O14 MOL 1 14.159 14.689 1.403 1.00 0.00 <br />
ATOM 15 C15 MOL 1 14.899 12.986 -0.210 1.00 0.00 <br />
ATOM 16 C16 MOL 1 17.969 16.420 1.747 1.00 0.00 <br />
ATOM 17 C17 MOL 1 20.056 16.927 0.663 1.00 0.00 <br />
ATOM 18 C18 MOL 1 13.566 16.775 0.184 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.281 17.721 -1.321 1.00 0.00 <br />
ATOM 20 O20 MOL 1 13.720 12.646 -0.346 1.00 0.00 <br />
ATOM 21 C21 MOL 1 21.259 16.286 0.008 1.00 0.00 <br />
ATOM 22 O22 MOL 1 12.278 16.816 0.702 1.00 0.00 <br />
ATOM 23 C23 MOL 1 14.040 17.798 -0.803 1.00 0.00 <br />
ATOM 24 C24 MOL 1 22.410 16.944 -0.094 1.00 0.00 <br />
ATOM 25 H25 MOL 1 19.357 15.031 -1.060 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|<jmol><br />
<jmolApplet><br />
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<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:49:10 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 17.558 13.998 -0.496 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.076 15.115 0.248 1.00 0.00 <br />
ATOM 3 C3 MOL 1 17.258 16.394 -0.557 1.00 0.00 <br />
ATOM 4 C4 MOL 1 15.561 15.011 0.531 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.860 15.228 1.589 1.00 0.00 <br />
ATOM 6 C6 MOL 1 16.778 17.574 0.073 1.00 0.00 <br />
ATOM 7 C7 MOL 1 18.653 16.799 -0.879 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.508 16.294 -1.921 1.00 0.00 <br />
ATOM 9 C9 MOL 1 15.127 16.315 1.434 1.00 0.00 <br />
ATOM 10 N10 MOL 1 14.843 14.899 -0.812 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.354 15.543 1.336 1.00 0.00 <br />
ATOM 12 C12 MOL 1 17.493 18.660 -0.426 1.00 0.00 <br />
ATOM 13 C13 MOL 1 15.791 17.648 0.954 1.00 0.00 <br />
ATOM 14 O14 MOL 1 18.548 18.231 -1.333 1.00 0.00 <br />
ATOM 15 C15 MOL 1 19.467 16.754 0.400 1.00 0.00 <br />
ATOM 16 C16 MOL 1 15.014 16.064 -1.686 1.00 0.00 <br />
ATOM 17 C17 MOL 1 13.406 14.609 -0.651 1.00 0.00 <br />
ATOM 18 C18 MOL 1 17.129 19.900 -0.114 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.387 18.995 1.400 1.00 0.00 <br />
ATOM 20 O20 MOL 1 20.317 17.624 0.613 1.00 0.00 <br />
ATOM 21 C21 MOL 1 13.178 13.073 -0.836 1.00 0.00 <br />
ATOM 22 O22 MOL 1 17.801 20.995 -0.638 1.00 0.00 <br />
ATOM 23 C23 MOL 1 16.014 20.069 0.881 1.00 0.00 <br />
ATOM 24 C24 MOL 1 11.870 12.702 -0.129 1.00 0.00 <br />
ATOM 25 C25 MOL 1 13.234 12.318 0.500 1.00 0.00 <br />
ATOM 26 H26 MOL 1 19.132 16.101 -1.579 1.00 0.00 <br />
ATOM 27 H27 MOL 1 15.339 14.101 1.101 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Naloxone<br />
|Naltrexone<br />
|-<br />
|}<br />
<br />
<br />
<br />
Both naloxone and naltrexone are competitive antagonists at the μ- and κ-opioid receptors, and to a lesser extent at δ-opioid receptors. The blockade of these receptors is what prevents the opiods such as morphine, from combining with these receptor sites thus preventing the side effects usually caused by morphine.<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroin<br />
|-<br />
|align="left" colspan="3" bgcolor="white"| <br />
|<br />
<jmol><br />
<jmolApplet><br />
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<inlineContents><br />
REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 14:36:05 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 12.755 17.484 0.278 1.00 0.00 <br />
ATOM 2 C2 MOL 1 14.165 17.279 0.259 1.00 0.00 <br />
ATOM 3 C3 MOL 1 14.598 16.294 -0.907 1.00 0.00 <br />
ATOM 4 C4 MOL 1 14.783 17.091 1.590 1.00 0.00 <br />
ATOM 5 C5 MOL 1 16.085 15.955 -0.655 1.00 0.00 <br />
ATOM 6 O6 MOL 1 13.944 14.927 -0.976 1.00 0.00 <br />
ATOM 7 C7 MOL 1 16.137 17.074 1.556 1.00 0.00 <br />
ATOM 8 C8 MOL 1 15.986 14.685 0.099 1.00 0.00 <br />
ATOM 9 C9 MOL 1 16.902 16.950 0.154 1.00 0.00 <br />
ATOM 10 C10 MOL 1 16.709 15.628 -2.040 1.00 0.00 <br />
ATOM 11 C11 MOL 1 14.759 14.077 -0.164 1.00 0.00 <br />
ATOM 12 C12 MOL 1 16.917 14.157 0.888 1.00 0.00 <br />
ATOM 13 C13 MOL 1 18.319 16.318 0.340 1.00 0.00 <br />
ATOM 14 C14 MOL 1 18.152 15.134 -1.868 1.00 0.00 <br />
ATOM 15 C15 MOL 1 14.483 12.853 0.325 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.177 14.972 1.210 1.00 0.00 <br />
ATOM 17 C17 MOL 1 16.666 12.844 1.470 1.00 0.00 <br />
ATOM 18 N18 MOL 1 18.922 16.087 -1.029 1.00 0.00 <br />
ATOM 19 O19 MOL 1 13.263 12.126 0.120 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.521 12.211 1.182 1.00 0.00 <br />
ATOM 21 C21 MOL 1 20.289 15.567 -0.871 1.00 0.00 <br />
ATOM 22 C22 MOL 1 12.251 12.761 -0.671 1.00 0.00 <br />
ATOM 23 H23 MOL 1 16.955 17.909 -0.379 1.00 0.00 <br />
ATOM 24 H24 MOL 1 14.357 16.925 -1.773 1.00 0.00 <br />
ATOM 25 H25 MOL 1 18.981 17.000 0.892 1.00 0.00 <br />
TER<br />
</inlineContents><br />
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|<br />
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<inlineContents><br />
REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 14:36:49 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.380 10.913 -0.058 1.00 0.00 <br />
ATOM 2 C2 MOL 1 22.712 10.864 -0.568 1.00 0.00 <br />
ATOM 3 C3 MOL 1 20.932 12.266 -0.071 1.00 0.00 <br />
ATOM 4 C4 MOL 1 23.445 9.558 -0.647 1.00 0.00 <br />
ATOM 5 O5 MOL 1 23.307 11.901 -0.901 1.00 0.00 <br />
ATOM 6 C6 MOL 1 19.783 12.581 0.994 1.00 0.00 <br />
ATOM 7 C7 MOL 1 20.757 12.864 -1.427 1.00 0.00 <br />
ATOM 8 C8 MOL 1 19.419 14.067 0.744 1.00 0.00 <br />
ATOM 9 O9 MOL 1 18.395 11.892 1.004 1.00 0.00 <br />
ATOM 10 C10 MOL 1 20.623 14.207 -1.407 1.00 0.00 <br />
ATOM 11 C11 MOL 1 18.168 13.977 -0.025 1.00 0.00 <br />
ATOM 12 C12 MOL 1 20.420 14.937 -0.012 1.00 0.00 <br />
ATOM 13 C13 MOL 1 19.051 14.641 2.138 1.00 0.00 <br />
ATOM 14 C14 MOL 1 17.546 12.770 0.237 1.00 0.00 <br />
ATOM 15 C15 MOL 1 17.644 14.930 -0.793 1.00 0.00 <br />
ATOM 16 C16 MOL 1 19.772 16.333 -0.179 1.00 0.00 <br />
ATOM 17 C17 MOL 1 18.538 16.078 2.002 1.00 0.00 <br />
ATOM 18 C18 MOL 1 16.298 12.542 -0.183 1.00 0.00 <br />
ATOM 19 C19 MOL 1 18.462 16.189 -1.090 1.00 0.00 <br />
ATOM 20 C20 MOL 1 16.318 14.720 -1.345 1.00 0.00 <br />
ATOM 21 N21 MOL 1 19.493 16.889 1.202 1.00 0.00 <br />
ATOM 22 O22 MOL 1 15.642 11.319 0.166 1.00 0.00 <br />
ATOM 23 C23 MOL 1 15.656 13.605 -1.022 1.00 0.00 <br />
ATOM 24 C24 MOL 1 18.950 18.247 1.075 1.00 0.00 <br />
ATOM 25 C25 MOL 1 14.263 11.150 -0.231 1.00 0.00 <br />
ATOM 26 C26 MOL 1 13.567 9.867 0.115 1.00 0.00 <br />
ATOM 27 O27 MOL 1 13.607 12.019 -0.820 1.00 0.00 <br />
ATOM 28 H28 MOL 1 21.358 14.995 0.556 1.00 0.00 <br />
ATOM 29 H29 MOL 1 20.362 12.366 1.900 1.00 0.00 <br />
ATOM 30 H30 MOL 1 20.458 17.021 -0.692 1.00 0.00 <br />
TER<br />
</inlineContents><br />
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|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br><br />
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br><br />
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.<br />
<br />
<br><br />
<br />
==Contraindications==<br />
<br />
*Acute Respiratory Depression <br />
*Acute Alcoholism <br />
*Acute pancreatitis (this may be a result of morphine use as well) <br />
*Renal failure (due to accumulation of the metabolite morphine-6-glucuronide) <br />
<br />
<br />
==Synthesis of Codeine from Morphine==<br />
<br><br />
[[Image:codeine_s.gif|thumb|Synthesis of Codeine]]<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]<br />
*Schmitz J, Stotts A, Rhoades H, Grabowski J. "Naltrexone and relapse prevention treatment for cocaine-dependent patients.". Addict Behav 26 (2): 167-80. PMID 11316375. <br />
*Chicago Recovery Alliance's naloxone distrobution project<br />
*Synthesis of codeine from morphine. Ai, Lin; Chen, Xiaoyuan; Zhang, Le. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005)</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sibutramine&diff=4366
It:Sibutramine
2006-10-26T14:53:28Z
<p>Ffs05: formated section divisions</p>
<hr />
<div>==<font color=red><font size=4>Sibutramine</font color></font size>==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|<br />
[[Image:sibutramine.gif]]<br />
|<jmol><br />
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<inlineContents><br />
HEADER Sibutramine NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 4.921 -0.468 -0.279 0.00 0.00 Cl+0<br />
ATOM 2 C 0 3.242 -0.131 0.004 0.00 0.00 C+0<br />
ATOM 3 C 0 2.815 0.248 1.264 0.00 0.00 C+0<br />
ATOM 4 C 0 1.477 0.515 1.489 0.00 0.00 C+0<br />
ATOM 5 C 0 0.567 0.404 0.455 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.891 0.695 0.700 0.00 0.00 C+0<br />
ATOM 7 C 0 -1.777 0.347 -0.498 0.00 0.00 C+0<br />
ATOM 8 N 0 -1.347 1.126 -1.667 0.00 0.00 N+0<br />
ATOM 9 C 0 -1.872 0.433 -2.852 0.00 0.00 C+0<br />
ATOM 10 C 0 -2.041 2.418 -1.591 0.00 0.00 C+0<br />
ATOM 11 C 0 -1.653 -1.146 -0.807 0.00 0.00 C+0<br />
ATOM 12 C 0 -2.199 -1.957 0.370 0.00 0.00 C+0<br />
ATOM 13 C 0 -3.661 -1.577 0.617 0.00 0.00 C+0<br />
ATOM 14 C 0 -2.108 -3.450 0.047 0.00 0.00 C+0<br />
ATOM 15 C 0 -1.414 0.139 2.035 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.210 1.447 2.178 0.00 0.00 C+0<br />
ATOM 17 C 0 -1.151 2.099 1.271 0.00 0.00 C+0<br />
ATOM 18 C 0 0.993 0.025 -0.805 0.00 0.00 C+0<br />
ATOM 19 C 0 2.331 -0.237 -1.032 0.00 0.00 C+0<br />
ATOM 20 H 0 3.526 0.334 2.072 0.00 0.00 H+0<br />
ATOM 21 H 0 1.144 0.811 2.472 0.00 0.00 H+0<br />
ATOM 22 H 0 -2.814 0.585 -0.264 0.00 0.00 H+0<br />
ATOM 23 H 0 -2.924 0.194 -2.696 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.771 1.079 -3.724 0.00 0.00 H+0<br />
ATOM 25 H 0 -1.310 -0.486 -3.013 0.00 0.00 H+0<br />
ATOM 26 H 0 -1.431 3.126 -1.030 0.00 0.00 H+0<br />
ATOM 27 H 0 -2.207 2.801 -2.599 0.00 0.00 H+0<br />
ATOM 28 H 0 -3.000 2.287 -1.090 0.00 0.00 H+0<br />
ATOM 29 H 0 -2.225 -1.380 -1.705 0.00 0.00 H+0<br />
ATOM 30 H 0 -0.605 -1.399 -0.967 0.00 0.00 H+0<br />
ATOM 31 H 0 -1.612 -1.742 1.263 0.00 0.00 H+0<br />
ATOM 32 H 0 -4.261 -1.862 -0.247 0.00 0.00 H+0<br />
ATOM 33 H 0 -4.027 -2.098 1.502 0.00 0.00 H+0<br />
ATOM 34 H 0 -3.735 -0.501 0.773 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.067 -3.721 -0.128 0.00 0.00 H+0<br />
ATOM 36 H 0 -2.497 -4.028 0.886 0.00 0.00 H+0<br />
ATOM 37 H 0 -2.695 -3.665 -0.845 0.00 0.00 H+0<br />
ATOM 38 H 0 -2.043 -0.745 1.923 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.638 0.015 2.791 0.00 0.00 H+0<br />
ATOM 40 H 0 -3.203 1.405 1.729 0.00 0.00 H+0<br />
ATOM 41 H 0 -2.221 1.843 3.194 0.00 0.00 H+0<br />
ATOM 42 H 0 -0.303 2.512 1.817 0.00 0.00 H+0<br />
ATOM 43 H 0 -1.568 2.797 0.545 0.00 0.00 H+0<br />
ATOM 44 H 0 0.281 -0.061 -1.612 0.00 0.00 H+0<br />
ATOM 45 H 0 2.664 -0.533 -2.016 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 50<br />
CONECT 2 1 19 3 0 NONE 51<br />
CONECT 3 2 4 20 0 NONE 52<br />
CONECT 4 3 5 21 0 NONE 53<br />
CONECT 5 4 6 18 0 NONE 54<br />
CONECT 6 5 17 7 15 NONE 55<br />
CONECT 7 6 8 11 22 NONE 56<br />
CONECT 8 7 9 10 0 NONE 57<br />
CONECT 9 8 23 24 25 NONE 58<br />
CONECT 10 8 26 27 28 NONE 59<br />
CONECT 11 7 12 29 30 NONE 60<br />
CONECT 12 11 13 14 31 NONE 61<br />
CONECT 13 12 32 33 34 NONE 62<br />
CONECT 14 12 35 36 37 NONE 63<br />
CONECT 15 6 16 38 39 NONE 64<br />
CONECT 16 15 17 40 41 NONE 65<br />
CONECT 17 16 6 42 43 NONE 66<br />
CONECT 18 5 19 44 0 NONE 67<br />
CONECT 19 18 2 45 0 NONE 68<br />
END NONE 69<br />
</inlineContents><br />
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<br />
==<font color=red><font size=4>'''How is Sibutramine synthesized?'''</font color></font size>==<br />
[[Image:synthesissibu.gif|right|100|Reaction scheme showing Sibutramine synthesis]]<br><br />
The reaction scheme shown on the right gives an overview of how Sibutramine is synthesized<sup>1</sup>. Known methods for preparation of crucial intermediate in the synthesis of ''1-1-(4-chlorophenyl)-1-cyanocyclobutane'' consist of cycloalkylation of 4-chlorophenylacetonitrile with 1,3-dibromopropane in the presence of such base/solvent systems as: NaH/DMSO/ether, solid KOH/DMSO/ether, solid KOH/toluene/quaternary ammonium salt as a catalyst (solid - liquid phase transfer catalysis, PTC). All of them are inconvenient for large scale applications. On the other hand, it is now commonly accepted, that liquid-liquid PTC (conc. aq. solution of NaOH as a base) is the best practical procedure for alkylation of carbanions of arylacetonitriles and their derivatives. However, with 1,3-dibromopropane under typical PTC conditions (50% NaOH aq. as a base) yields of 1-aryl-1-cyanocyclobutanes are low, b-elimination of HBr from the alkylating agent is often observed, leading to mono- and diallylated arylacetonitriles as by product, which are difficult to separate.<br />
<br />
It was experimentally observed that a simple change of 50% NaOH for 60% KOH overcomes all the difficulties mentioned above. Cycloalkylation of 4-chlorophenylacetonitrile with 1,3-dibromopropane carried out in the presence of 60% KOH and tetrabutylammonium bromide (TBAB) as a catalyst in toluene as a solvent proceeds in high yield, b-elimination of HBr from the alkylating agent practically does not proceed and isolation of ''1-1-(4-chlorophenyl)-1-cyanocyclobutane'' is pretty simple. This process was performed on a 10 mol scale, with the yields exceeding 70%.<br />
<br><br />
<br><br />
<br><br />
<br><br />
<br><br />
== <font size=4><font color=red>'''How does Sibutramine aid in weight loss?'''</font color></font size> <br> <br>==<br />
Sibutramine pills<sup>5</sup>:<br><br><br />
[[Image:sibutramine.jpg|60|Sibutramine pills]]<br><br><br />
Sibutramine primarily works by increasing feelings of satiety and reducing appetite. It is recommended to patients with a BMI of 30kg m<sup>-2</sup> or more for aiding weight loss by reducing appetite and increasing satiety.<br><br />
It increases blood pressure in some patients<sup>4</sup> and therefore blood pressure must be monitored during treatment to ensure that it does not become dangerously high.<br><br><br />
However, the weight loss as a result of using Sibutramine does not come without a price. Side effects of Sibutramine include dry mouth, constipation and insomnia. Less common side effects include headache, increased sweating, increased blood pressure and increased heart rate. Of these, the issue of increased blood pressure is the most concerning, but it is less common and since patients with obesity are regularly monitored by their doctors for changes in blood pressure, this risk is mitigated somewhat<sup>2</sup>. In addition, Sibutramine should not be prescribed for people with a history of coronary artery disease, congestive heart failure, arrhythmias or stroke, as it may dangerously increase the individual's heart rate and/or blood pressure.<br><br />
<br><br />
==<font size=4><font color=red>'''Working principles behind Sibutramine'''</font color></font size><br> <br>==<br />
[[Image:neuro.gif|right|100|Working principle behind Sibutramine]]<br />
Sibutramine (commercially known as Meridia®) is an equipotent serotonin and norepinephrine reuptake inhibitor (SNRI), which means it has an equal effect on serotonin (a brain neurotransmitter which generally promotes a calming feeling) and norepinephrine (a stimulant). The diagram on the right shows how this is brought about<sup>6</sup>. Research indicates that these brain chemicals have an effect on appetite and satiety.<br><br />
<br />
Animals given sibutramine have shown an increase in metabolic rate<sup>3</sup>, but human studies have not been conclusive. The reasons for the difference between animals and humans is not clear but may be due to the small number of subjects tested and the small effect of the drug on energy expenditure. However, even small increases in thermogenesis could be clinically significant in weight loss and weight maintenance. (Thermogenesis refers to increased fat loss through raising the body's core temperature or through an increased caloric use as a result of an heightened energy/metabolic state)<br><br />
<br><br />
==<font size=4><font color=red>'''References'''</font color><font size><br><br>==<br />
1) [http://www.science24.com/paper/6574 Science24.com/confernces]<br><br />
2) ''The effect of sibutramine-assisted weight loss in men with obstructive sleep apnoea'',International Journal of Obesity, 2 May 2006<br><br />
3) Malhotra A, White DP. Obstructive sleep apnoea. Lancet 2002; 360: 237–245<br><br />
4) Kim SH, Lee YM, Jee SH, Nam CM. Effect of sibutramine on weight loss and blood pressure: a meta-analysis of controlled trials. Obes Res 2003; 11: 1116–1123<br><br />
5) [http://www.myelectronicpharmacy.com My electronic pharmacy]<br><br />
6) [http://images.google.co.uk/imgres?imgurl=http://www.weightloss-news.com/graphics.htg/mermov.gif&imgrefurl=http://www.obesity-news.com/merfaq.htm&h=184&w=300&sz=40&hl=en&start=1&tbnid=ieLgEWX8ICsvJM:&tbnh=71&tbnw=116&prev=/images%3Fq%3Dsibutramine%26ndsp%3D20%26svnum%3D10%26hl%3Den%26lr%3D%26sa%3DN Obesity Meds and Research News]</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sibutramine&diff=4344
It:Sibutramine
2006-10-26T14:42:21Z
<p>Ffs05: replaced 2D picture of piperine with that of sibutramine</p>
<hr />
<div>{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|<br />
[[Image:sibutramine.gif]]<br />
|<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
HEADER Sibutramine NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 4.921 -0.468 -0.279 0.00 0.00 Cl+0<br />
ATOM 2 C 0 3.242 -0.131 0.004 0.00 0.00 C+0<br />
ATOM 3 C 0 2.815 0.248 1.264 0.00 0.00 C+0<br />
ATOM 4 C 0 1.477 0.515 1.489 0.00 0.00 C+0<br />
ATOM 5 C 0 0.567 0.404 0.455 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.891 0.695 0.700 0.00 0.00 C+0<br />
ATOM 7 C 0 -1.777 0.347 -0.498 0.00 0.00 C+0<br />
ATOM 8 N 0 -1.347 1.126 -1.667 0.00 0.00 N+0<br />
ATOM 9 C 0 -1.872 0.433 -2.852 0.00 0.00 C+0<br />
ATOM 10 C 0 -2.041 2.418 -1.591 0.00 0.00 C+0<br />
ATOM 11 C 0 -1.653 -1.146 -0.807 0.00 0.00 C+0<br />
ATOM 12 C 0 -2.199 -1.957 0.370 0.00 0.00 C+0<br />
ATOM 13 C 0 -3.661 -1.577 0.617 0.00 0.00 C+0<br />
ATOM 14 C 0 -2.108 -3.450 0.047 0.00 0.00 C+0<br />
ATOM 15 C 0 -1.414 0.139 2.035 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.210 1.447 2.178 0.00 0.00 C+0<br />
ATOM 17 C 0 -1.151 2.099 1.271 0.00 0.00 C+0<br />
ATOM 18 C 0 0.993 0.025 -0.805 0.00 0.00 C+0<br />
ATOM 19 C 0 2.331 -0.237 -1.032 0.00 0.00 C+0<br />
ATOM 20 H 0 3.526 0.334 2.072 0.00 0.00 H+0<br />
ATOM 21 H 0 1.144 0.811 2.472 0.00 0.00 H+0<br />
ATOM 22 H 0 -2.814 0.585 -0.264 0.00 0.00 H+0<br />
ATOM 23 H 0 -2.924 0.194 -2.696 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.771 1.079 -3.724 0.00 0.00 H+0<br />
ATOM 25 H 0 -1.310 -0.486 -3.013 0.00 0.00 H+0<br />
ATOM 26 H 0 -1.431 3.126 -1.030 0.00 0.00 H+0<br />
ATOM 27 H 0 -2.207 2.801 -2.599 0.00 0.00 H+0<br />
ATOM 28 H 0 -3.000 2.287 -1.090 0.00 0.00 H+0<br />
ATOM 29 H 0 -2.225 -1.380 -1.705 0.00 0.00 H+0<br />
ATOM 30 H 0 -0.605 -1.399 -0.967 0.00 0.00 H+0<br />
ATOM 31 H 0 -1.612 -1.742 1.263 0.00 0.00 H+0<br />
ATOM 32 H 0 -4.261 -1.862 -0.247 0.00 0.00 H+0<br />
ATOM 33 H 0 -4.027 -2.098 1.502 0.00 0.00 H+0<br />
ATOM 34 H 0 -3.735 -0.501 0.773 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.067 -3.721 -0.128 0.00 0.00 H+0<br />
ATOM 36 H 0 -2.497 -4.028 0.886 0.00 0.00 H+0<br />
ATOM 37 H 0 -2.695 -3.665 -0.845 0.00 0.00 H+0<br />
ATOM 38 H 0 -2.043 -0.745 1.923 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.638 0.015 2.791 0.00 0.00 H+0<br />
ATOM 40 H 0 -3.203 1.405 1.729 0.00 0.00 H+0<br />
ATOM 41 H 0 -2.221 1.843 3.194 0.00 0.00 H+0<br />
ATOM 42 H 0 -0.303 2.512 1.817 0.00 0.00 H+0<br />
ATOM 43 H 0 -1.568 2.797 0.545 0.00 0.00 H+0<br />
ATOM 44 H 0 0.281 -0.061 -1.612 0.00 0.00 H+0<br />
ATOM 45 H 0 2.664 -0.533 -2.016 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 50<br />
CONECT 2 1 19 3 0 NONE 51<br />
CONECT 3 2 4 20 0 NONE 52<br />
CONECT 4 3 5 21 0 NONE 53<br />
CONECT 5 4 6 18 0 NONE 54<br />
CONECT 6 5 17 7 15 NONE 55<br />
CONECT 7 6 8 11 22 NONE 56<br />
CONECT 8 7 9 10 0 NONE 57<br />
CONECT 9 8 23 24 25 NONE 58<br />
CONECT 10 8 26 27 28 NONE 59<br />
CONECT 11 7 12 29 30 NONE 60<br />
CONECT 12 11 13 14 31 NONE 61<br />
CONECT 13 12 32 33 34 NONE 62<br />
CONECT 14 12 35 36 37 NONE 63<br />
CONECT 15 6 16 38 39 NONE 64<br />
CONECT 16 15 17 40 41 NONE 65<br />
CONECT 17 16 6 42 43 NONE 66<br />
CONECT 18 5 19 44 0 NONE 67<br />
CONECT 19 18 2 45 0 NONE 68<br />
END NONE 69<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
<br />
<br />
<br />
<br />
<br><br />
<br />
<font color=red><font size=4>'''How is Sibutramine synthesized?'''</font color></font size><br />
[[Image:synthesissibu.gif|right|100|Reaction scheme showing Sibutramine synthesis]]<br><br />
The reaction scheme shown on the right gives an overview of how Sibutramine is synthesized<sup>1</sup>. Known methods for preparation of crucial intermediate in the synthesis of ''1-1-(4-chlorophenyl)-1-cyanocyclobutane'' consist of cycloalkylation of 4-chlorophenylacetonitrile with 1,3-dibromopropane in the presence of such base/solvent systems as: NaH/DMSO/ether, solid KOH/DMSO/ether, solid KOH/toluene/quaternary ammonium salt as a catalyst (solid - liquid phase transfer catalysis, PTC). All of them are inconvenient for large scale applications. On the other hand, it is now commonly accepted, that liquid-liquid PTC (conc. aq. solution of NaOH as a base) is the best practical procedure for alkylation of carbanions of arylacetonitriles and their derivatives. However, with 1,3-dibromopropane under typical PTC conditions (50% NaOH aq. as a base) yields of 1-aryl-1-cyanocyclobutanes are low, b-elimination of HBr from the alkylating agent is often observed, leading to mono- and diallylated arylacetonitriles as by product, which are difficult to separate.<br />
<br />
It was experimentally observed that a simple change of 50% NaOH for 60% KOH overcomes all the difficulties mentioned above. Cycloalkylation of 4-chlorophenylacetonitrile with 1,3-dibromopropane carried out in the presence of 60% KOH and tetrabutylammonium bromide (TBAB) as a catalyst in toluene as a solvent proceeds in high yield, b-elimination of HBr from the alkylating agent practically does not proceed and isolation of ''1-1-(4-chlorophenyl)-1-cyanocyclobutane'' is pretty simple. This process was performed on a 10 mol scale, with the yields exceeding 70%.<br />
<br><br />
<br><br />
<br><br />
<br><br />
<br><br />
<font size=4><font color=red>'''How does Sibutramine aid in weight loss?'''</font color></font size><br><br><br />
Sibutramine pills<sup>5</sup>:<br><br><br />
[[Image:sibutramine.jpg|60|Sibutramine pills]]<br><br><br />
Sibutramine primarily works by increasing feelings of satiety and reducing appetite. It is recommended to patients with a BMI of 30kg m<sup>-2</sup> or more for aiding weight loss by reducing appetite and increasing satiety.<br><br />
It increases blood pressure in some patients<sup>4</sup> and therefore blood pressure must be monitored during treatment to ensure that it does not become dangerously high.<br><br><br />
However, the weight loss as a result of using Sibutramine does not come without a price. Side effects of Sibutramine include dry mouth, constipation and insomnia. Less common side effects include headache, increased sweating, increased blood pressure and increased heart rate. Of these, the issue of increased blood pressure is the most concerning, but it is less common and since patients with obesity are regularly monitored by their doctors for changes in blood pressure, this risk is mitigated somewhat<sup>2</sup>. In addition, Sibutramine should not be prescribed for people with a history of coronary artery disease, congestive heart failure, arrhythmias or stroke, as it may dangerously increase the individual's heart rate and/or blood pressure.<br><br />
<br><br />
<font size=4><font color=red>'''Working principles behind Sibutramine'''</font color></font size><br><br><br />
[[Image:neuro.gif|right|100|Working principle behind Sibutramine]]<br />
Sibutramine (commercially known as Meridia®) is an equipotent serotonin and norepinephrine reuptake inhibitor (SNRI), which means it has an equal effect on serotonin (a brain neurotransmitter which generally promotes a calming feeling) and norepinephrine (a stimulant). The diagram on the right shows how this is brought about<sup>6</sup>. Research indicates that these brain chemicals have an effect on appetite and satiety.<br><br />
<br />
Animals given sibutramine have shown an increase in metabolic rate<sup>3</sup>, but human studies have not been conclusive. The reasons for the difference between animals and humans is not clear but may be due to the small number of subjects tested and the small effect of the drug on energy expenditure. However, even small increases in thermogenesis could be clinically significant in weight loss and weight maintenance. (Thermogenesis refers to increased fat loss through raising the body's core temperature or through an increased caloric use as a result of an heightened energy/metabolic state)<br><br />
<br><br />
<font size=4><font color=red>'''References'''</font color><font size><br><br><br />
1) [http://www.science24.com/paper/6574 Science24.com/confernces]<br><br />
2) ''The effect of sibutramine-assisted weight loss in men with obstructive sleep apnoea'',International Journal of Obesity, 2 May 2006<br><br />
3) Malhotra A, White DP. Obstructive sleep apnoea. Lancet 2002; 360: 237–245<br><br />
4) Kim SH, Lee YM, Jee SH, Nam CM. Effect of sibutramine on weight loss and blood pressure: a meta-analysis of controlled trials. Obes Res 2003; 11: 1116–1123<br><br />
5) [http://www.myelectronicpharmacy.com My electronic pharmacy]<br><br />
6) [http://images.google.co.uk/imgres?imgurl=http://www.weightloss-news.com/graphics.htg/mermov.gif&imgrefurl=http://www.obesity-news.com/merfaq.htm&h=184&w=300&sz=40&hl=en&start=1&tbnid=ieLgEWX8ICsvJM:&tbnh=71&tbnw=116&prev=/images%3Fq%3Dsibutramine%26ndsp%3D20%26svnum%3D10%26hl%3Den%26lr%3D%26sa%3DN Obesity Meds and Research News]</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Sibutramine&diff=4335
It:Sibutramine
2006-10-26T14:36:11Z
<p>Ffs05: edited 3D structure</p>
<hr />
<div>[[Image:piperine.gif]]<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
HEADER Sibutramine NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 20-Oct-06 0 NONE 4<br />
ATOM 1 Cl 0 4.921 -0.468 -0.279 0.00 0.00 Cl+0<br />
ATOM 2 C 0 3.242 -0.131 0.004 0.00 0.00 C+0<br />
ATOM 3 C 0 2.815 0.248 1.264 0.00 0.00 C+0<br />
ATOM 4 C 0 1.477 0.515 1.489 0.00 0.00 C+0<br />
ATOM 5 C 0 0.567 0.404 0.455 0.00 0.00 C+0<br />
ATOM 6 C 0 -0.891 0.695 0.700 0.00 0.00 C+0<br />
ATOM 7 C 0 -1.777 0.347 -0.498 0.00 0.00 C+0<br />
ATOM 8 N 0 -1.347 1.126 -1.667 0.00 0.00 N+0<br />
ATOM 9 C 0 -1.872 0.433 -2.852 0.00 0.00 C+0<br />
ATOM 10 C 0 -2.041 2.418 -1.591 0.00 0.00 C+0<br />
ATOM 11 C 0 -1.653 -1.146 -0.807 0.00 0.00 C+0<br />
ATOM 12 C 0 -2.199 -1.957 0.370 0.00 0.00 C+0<br />
ATOM 13 C 0 -3.661 -1.577 0.617 0.00 0.00 C+0<br />
ATOM 14 C 0 -2.108 -3.450 0.047 0.00 0.00 C+0<br />
ATOM 15 C 0 -1.414 0.139 2.035 0.00 0.00 C+0<br />
ATOM 16 C 0 -2.210 1.447 2.178 0.00 0.00 C+0<br />
ATOM 17 C 0 -1.151 2.099 1.271 0.00 0.00 C+0<br />
ATOM 18 C 0 0.993 0.025 -0.805 0.00 0.00 C+0<br />
ATOM 19 C 0 2.331 -0.237 -1.032 0.00 0.00 C+0<br />
ATOM 20 H 0 3.526 0.334 2.072 0.00 0.00 H+0<br />
ATOM 21 H 0 1.144 0.811 2.472 0.00 0.00 H+0<br />
ATOM 22 H 0 -2.814 0.585 -0.264 0.00 0.00 H+0<br />
ATOM 23 H 0 -2.924 0.194 -2.696 0.00 0.00 H+0<br />
ATOM 24 H 0 -1.771 1.079 -3.724 0.00 0.00 H+0<br />
ATOM 25 H 0 -1.310 -0.486 -3.013 0.00 0.00 H+0<br />
ATOM 26 H 0 -1.431 3.126 -1.030 0.00 0.00 H+0<br />
ATOM 27 H 0 -2.207 2.801 -2.599 0.00 0.00 H+0<br />
ATOM 28 H 0 -3.000 2.287 -1.090 0.00 0.00 H+0<br />
ATOM 29 H 0 -2.225 -1.380 -1.705 0.00 0.00 H+0<br />
ATOM 30 H 0 -0.605 -1.399 -0.967 0.00 0.00 H+0<br />
ATOM 31 H 0 -1.612 -1.742 1.263 0.00 0.00 H+0<br />
ATOM 32 H 0 -4.261 -1.862 -0.247 0.00 0.00 H+0<br />
ATOM 33 H 0 -4.027 -2.098 1.502 0.00 0.00 H+0<br />
ATOM 34 H 0 -3.735 -0.501 0.773 0.00 0.00 H+0<br />
ATOM 35 H 0 -1.067 -3.721 -0.128 0.00 0.00 H+0<br />
ATOM 36 H 0 -2.497 -4.028 0.886 0.00 0.00 H+0<br />
ATOM 37 H 0 -2.695 -3.665 -0.845 0.00 0.00 H+0<br />
ATOM 38 H 0 -2.043 -0.745 1.923 0.00 0.00 H+0<br />
ATOM 39 H 0 -0.638 0.015 2.791 0.00 0.00 H+0<br />
ATOM 40 H 0 -3.203 1.405 1.729 0.00 0.00 H+0<br />
ATOM 41 H 0 -2.221 1.843 3.194 0.00 0.00 H+0<br />
ATOM 42 H 0 -0.303 2.512 1.817 0.00 0.00 H+0<br />
ATOM 43 H 0 -1.568 2.797 0.545 0.00 0.00 H+0<br />
ATOM 44 H 0 0.281 -0.061 -1.612 0.00 0.00 H+0<br />
ATOM 45 H 0 2.664 -0.533 -2.016 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 50<br />
CONECT 2 1 19 3 0 NONE 51<br />
CONECT 3 2 4 20 0 NONE 52<br />
CONECT 4 3 5 21 0 NONE 53<br />
CONECT 5 4 6 18 0 NONE 54<br />
CONECT 6 5 17 7 15 NONE 55<br />
CONECT 7 6 8 11 22 NONE 56<br />
CONECT 8 7 9 10 0 NONE 57<br />
CONECT 9 8 23 24 25 NONE 58<br />
CONECT 10 8 26 27 28 NONE 59<br />
CONECT 11 7 12 29 30 NONE 60<br />
CONECT 12 11 13 14 31 NONE 61<br />
CONECT 13 12 32 33 34 NONE 62<br />
CONECT 14 12 35 36 37 NONE 63<br />
CONECT 15 6 16 38 39 NONE 64<br />
CONECT 16 15 17 40 41 NONE 65<br />
CONECT 17 16 6 42 43 NONE 66<br />
CONECT 18 5 19 44 0 NONE 67<br />
CONECT 19 18 2 45 0 NONE 68<br />
END NONE 69<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br><br />
<br />
<font color=red><font size=4>'''How is Sibutramine synthesized?'''</font color></font size><br />
[[Image:synthesissibu.gif|right|100|Reaction scheme showing Sibutramine synthesis]]<br><br />
The reaction scheme shown on the right gives an overview of how Sibutramine is synthesized<sup>1</sup>. Known methods for preparation of crucial intermediate in the synthesis of ''1-1-(4-chlorophenyl)-1-cyanocyclobutane'' consist of cycloalkylation of 4-chlorophenylacetonitrile with 1,3-dibromopropane in the presence of such base/solvent systems as: NaH/DMSO/ether, solid KOH/DMSO/ether, solid KOH/toluene/quaternary ammonium salt as a catalyst (solid - liquid phase transfer catalysis, PTC). All of them are inconvenient for large scale applications. On the other hand, it is now commonly accepted, that liquid-liquid PTC (conc. aq. solution of NaOH as a base) is the best practical procedure for alkylation of carbanions of arylacetonitriles and their derivatives. However, with 1,3-dibromopropane under typical PTC conditions (50% NaOH aq. as a base) yields of 1-aryl-1-cyanocyclobutanes are low, b-elimination of HBr from the alkylating agent is often observed, leading to mono- and diallylated arylacetonitriles as by product, which are difficult to separate.<br />
<br />
It was experimentally observed that a simple change of 50% NaOH for 60% KOH overcomes all the difficulties mentioned above. Cycloalkylation of 4-chlorophenylacetonitrile with 1,3-dibromopropane carried out in the presence of 60% KOH and tetrabutylammonium bromide (TBAB) as a catalyst in toluene as a solvent proceeds in high yield, b-elimination of HBr from the alkylating agent practically does not proceed and isolation of ''1-1-(4-chlorophenyl)-1-cyanocyclobutane'' is pretty simple. This process was performed on a 10 mol scale, with the yields exceeding 70%.<br />
<br><br />
<br><br />
<br><br />
<br><br />
<br><br />
<font size=4><font color=red>'''How does Sibutramine aid in weight loss?'''</font color></font size><br><br><br />
Sibutramine pills<sup>5</sup>:<br><br><br />
[[Image:sibutramine.jpg|60|Sibutramine pills]]<br><br><br />
Sibutramine primarily works by increasing feelings of satiety and reducing appetite. It is recommended to patients with a BMI of 30kg m<sup>-2</sup> or more for aiding weight loss by reducing appetite and increasing satiety.<br><br />
It increases blood pressure in some patients<sup>4</sup> and therefore blood pressure must be monitored during treatment to ensure that it does not become dangerously high.<br><br><br />
However, the weight loss as a result of using Sibutramine does not come without a price. Side effects of Sibutramine include dry mouth, constipation and insomnia. Less common side effects include headache, increased sweating, increased blood pressure and increased heart rate. Of these, the issue of increased blood pressure is the most concerning, but it is less common and since patients with obesity are regularly monitored by their doctors for changes in blood pressure, this risk is mitigated somewhat<sup>2</sup>. In addition, Sibutramine should not be prescribed for people with a history of coronary artery disease, congestive heart failure, arrhythmias or stroke, as it may dangerously increase the individual's heart rate and/or blood pressure.<br><br />
<br><br />
<font size=4><font color=red>'''Working principles behind Sibutramine'''</font color></font size><br><br><br />
[[Image:neuro.gif|right|100|Working principle behind Sibutramine]]<br />
Sibutramine (commercially known as Meridia®) is an equipotent serotonin and norepinephrine reuptake inhibitor (SNRI), which means it has an equal effect on serotonin (a brain neurotransmitter which generally promotes a calming feeling) and norepinephrine (a stimulant). The diagram on the right shows how this is brought about<sup>6</sup>. Research indicates that these brain chemicals have an effect on appetite and satiety.<br><br />
<br />
Animals given sibutramine have shown an increase in metabolic rate<sup>3</sup>, but human studies have not been conclusive. The reasons for the difference between animals and humans is not clear but may be due to the small number of subjects tested and the small effect of the drug on energy expenditure. However, even small increases in thermogenesis could be clinically significant in weight loss and weight maintenance. (Thermogenesis refers to increased fat loss through raising the body's core temperature or through an increased caloric use as a result of an heightened energy/metabolic state)<br><br />
<br><br />
<font size=4><font color=red>'''References'''</font color><font size><br><br><br />
1) [http://www.science24.com/paper/6574 Science24.com/confernces]<br><br />
2) ''The effect of sibutramine-assisted weight loss in men with obstructive sleep apnoea'',International Journal of Obesity, 2 May 2006<br><br />
3) Malhotra A, White DP. Obstructive sleep apnoea. Lancet 2002; 360: 237–245<br><br />
4) Kim SH, Lee YM, Jee SH, Nam CM. Effect of sibutramine on weight loss and blood pressure: a meta-analysis of controlled trials. Obes Res 2003; 11: 1116–1123<br><br />
5) [http://www.myelectronicpharmacy.com My electronic pharmacy]<br><br />
6) [http://images.google.co.uk/imgres?imgurl=http://www.weightloss-news.com/graphics.htg/mermov.gif&imgrefurl=http://www.obesity-news.com/merfaq.htm&h=184&w=300&sz=40&hl=en&start=1&tbnid=ieLgEWX8ICsvJM:&tbnh=71&tbnw=116&prev=/images%3Fq%3Dsibutramine%26ndsp%3D20%26svnum%3D10%26hl%3Den%26lr%3D%26sa%3DN Obesity Meds and Research News]</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=4330
It:Morphine
2006-10-26T14:29:12Z
<p>Ffs05: edited 3d structures</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
== Properties of Morphine ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data''' <br />
|-<br />
| IUPAC Name<br />
| align="center"|7,8-didehydro-<br />
4,5-epoxy-17-methylmorphinan-3,6-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub><br />
|-<br />
| Molar Mass<br />
| align="center"|285.4 g/mol<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''<br />
|-<br />
| Bioavailability<br />
| align="center"|... ~30%<br />
|-<br />
| Protein binding<br />
| align="center"|... 30–40%<br />
|-<br />
| Metabolism<br />
| align="center"|... Hepatic 90%<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''<br />
|-<br />
| Pregnancy cat.<br />
| align="center"| C(AU) C(US)<br />
|-<br />
| Legal status<br />
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only<br />
|-<br />
| Dependence Liability<br />
| align="center"| Extremely High<br />
|-<br />
| Routes<br />
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
<br />
<br />
==Pharmacology of Morphine==<br />
<br />
Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:48:06 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 18.255 13.156 0.573 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.569 14.167 -0.163 1.00 0.00 <br />
ATOM 3 C3 MOL 1 16.417 14.732 0.663 1.00 0.00 <br />
ATOM 4 C4 MOL 1 18.496 15.366 -0.471 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.015 13.567 -1.482 1.00 0.00 <br />
ATOM 6 C6 MOL 1 15.693 15.779 0.018 1.00 0.00 <br />
ATOM 7 C7 MOL 1 15.307 13.777 1.020 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.942 15.313 2.010 1.00 0.00 <br />
ATOM 9 C9 MOL 1 17.646 16.451 -1.361 1.00 0.00 <br />
ATOM 10 N10 MOL 1 19.019 15.899 0.861 1.00 0.00 <br />
ATOM 11 C11 MOL 1 15.959 12.473 -1.196 1.00 0.00 <br />
ATOM 12 C12 MOL 1 14.403 15.799 0.518 1.00 0.00 <br />
ATOM 13 C13 MOL 1 16.179 16.645 -0.862 1.00 0.00 <br />
ATOM 14 O14 MOL 1 14.159 14.689 1.403 1.00 0.00 <br />
ATOM 15 C15 MOL 1 14.899 12.986 -0.210 1.00 0.00 <br />
ATOM 16 C16 MOL 1 17.969 16.420 1.747 1.00 0.00 <br />
ATOM 17 C17 MOL 1 20.056 16.927 0.663 1.00 0.00 <br />
ATOM 18 C18 MOL 1 13.566 16.775 0.184 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.281 17.721 -1.321 1.00 0.00 <br />
ATOM 20 O20 MOL 1 13.720 12.646 -0.346 1.00 0.00 <br />
ATOM 21 C21 MOL 1 21.259 16.286 0.008 1.00 0.00 <br />
ATOM 22 O22 MOL 1 12.278 16.816 0.702 1.00 0.00 <br />
ATOM 23 C23 MOL 1 14.040 17.798 -0.803 1.00 0.00 <br />
ATOM 24 C24 MOL 1 22.410 16.944 -0.094 1.00 0.00 <br />
ATOM 25 H25 MOL 1 19.357 15.031 -1.060 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:49:10 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 17.558 13.998 -0.496 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.076 15.115 0.248 1.00 0.00 <br />
ATOM 3 C3 MOL 1 17.258 16.394 -0.557 1.00 0.00 <br />
ATOM 4 C4 MOL 1 15.561 15.011 0.531 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.860 15.228 1.589 1.00 0.00 <br />
ATOM 6 C6 MOL 1 16.778 17.574 0.073 1.00 0.00 <br />
ATOM 7 C7 MOL 1 18.653 16.799 -0.879 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.508 16.294 -1.921 1.00 0.00 <br />
ATOM 9 C9 MOL 1 15.127 16.315 1.434 1.00 0.00 <br />
ATOM 10 N10 MOL 1 14.843 14.899 -0.812 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.354 15.543 1.336 1.00 0.00 <br />
ATOM 12 C12 MOL 1 17.493 18.660 -0.426 1.00 0.00 <br />
ATOM 13 C13 MOL 1 15.791 17.648 0.954 1.00 0.00 <br />
ATOM 14 O14 MOL 1 18.548 18.231 -1.333 1.00 0.00 <br />
ATOM 15 C15 MOL 1 19.467 16.754 0.400 1.00 0.00 <br />
ATOM 16 C16 MOL 1 15.014 16.064 -1.686 1.00 0.00 <br />
ATOM 17 C17 MOL 1 13.406 14.609 -0.651 1.00 0.00 <br />
ATOM 18 C18 MOL 1 17.129 19.900 -0.114 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.387 18.995 1.400 1.00 0.00 <br />
ATOM 20 O20 MOL 1 20.317 17.624 0.613 1.00 0.00 <br />
ATOM 21 C21 MOL 1 13.178 13.073 -0.836 1.00 0.00 <br />
ATOM 22 O22 MOL 1 17.801 20.995 -0.638 1.00 0.00 <br />
ATOM 23 C23 MOL 1 16.014 20.069 0.881 1.00 0.00 <br />
ATOM 24 C24 MOL 1 11.870 12.702 -0.129 1.00 0.00 <br />
ATOM 25 C25 MOL 1 13.234 12.318 0.500 1.00 0.00 <br />
ATOM 26 H26 MOL 1 19.132 16.101 -1.579 1.00 0.00 <br />
ATOM 27 H27 MOL 1 15.339 14.101 1.101 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Naloxone<br />
|Naltrexone<br />
|-<br />
|}<br />
<br />
<br />
<br />
Both naloxone and naltrexone are competitive antagonists at the μ- and κ-opioid receptors, and to a lesser extent at δ-opioid receptors. The blockade of these receptors is what prevents the opiods such as morphine, from combining with these receptor sites thus preventing the side effects usually caused by morphine.<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroin<br />
|-<br />
|align="left" colspan="3" bgcolor="white"| <br />
|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 14:36:05 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 12.755 17.484 0.278 1.00 0.00 <br />
ATOM 2 C2 MOL 1 14.165 17.279 0.259 1.00 0.00 <br />
ATOM 3 C3 MOL 1 14.598 16.294 -0.907 1.00 0.00 <br />
ATOM 4 C4 MOL 1 14.783 17.091 1.590 1.00 0.00 <br />
ATOM 5 C5 MOL 1 16.085 15.955 -0.655 1.00 0.00 <br />
ATOM 6 O6 MOL 1 13.944 14.927 -0.976 1.00 0.00 <br />
ATOM 7 C7 MOL 1 16.137 17.074 1.556 1.00 0.00 <br />
ATOM 8 C8 MOL 1 15.986 14.685 0.099 1.00 0.00 <br />
ATOM 9 C9 MOL 1 16.902 16.950 0.154 1.00 0.00 <br />
ATOM 10 C10 MOL 1 16.709 15.628 -2.040 1.00 0.00 <br />
ATOM 11 C11 MOL 1 14.759 14.077 -0.164 1.00 0.00 <br />
ATOM 12 C12 MOL 1 16.917 14.157 0.888 1.00 0.00 <br />
ATOM 13 C13 MOL 1 18.319 16.318 0.340 1.00 0.00 <br />
ATOM 14 C14 MOL 1 18.152 15.134 -1.868 1.00 0.00 <br />
ATOM 15 C15 MOL 1 14.483 12.853 0.325 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.177 14.972 1.210 1.00 0.00 <br />
ATOM 17 C17 MOL 1 16.666 12.844 1.470 1.00 0.00 <br />
ATOM 18 N18 MOL 1 18.922 16.087 -1.029 1.00 0.00 <br />
ATOM 19 O19 MOL 1 13.263 12.126 0.120 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.521 12.211 1.182 1.00 0.00 <br />
ATOM 21 C21 MOL 1 20.289 15.567 -0.871 1.00 0.00 <br />
ATOM 22 C22 MOL 1 12.251 12.761 -0.671 1.00 0.00 <br />
ATOM 23 H23 MOL 1 16.955 17.909 -0.379 1.00 0.00 <br />
ATOM 24 H24 MOL 1 14.357 16.925 -1.773 1.00 0.00 <br />
ATOM 25 H25 MOL 1 18.981 17.000 0.892 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 14:36:49 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.380 10.913 -0.058 1.00 0.00 <br />
ATOM 2 C2 MOL 1 22.712 10.864 -0.568 1.00 0.00 <br />
ATOM 3 C3 MOL 1 20.932 12.266 -0.071 1.00 0.00 <br />
ATOM 4 C4 MOL 1 23.445 9.558 -0.647 1.00 0.00 <br />
ATOM 5 O5 MOL 1 23.307 11.901 -0.901 1.00 0.00 <br />
ATOM 6 C6 MOL 1 19.783 12.581 0.994 1.00 0.00 <br />
ATOM 7 C7 MOL 1 20.757 12.864 -1.427 1.00 0.00 <br />
ATOM 8 C8 MOL 1 19.419 14.067 0.744 1.00 0.00 <br />
ATOM 9 O9 MOL 1 18.395 11.892 1.004 1.00 0.00 <br />
ATOM 10 C10 MOL 1 20.623 14.207 -1.407 1.00 0.00 <br />
ATOM 11 C11 MOL 1 18.168 13.977 -0.025 1.00 0.00 <br />
ATOM 12 C12 MOL 1 20.420 14.937 -0.012 1.00 0.00 <br />
ATOM 13 C13 MOL 1 19.051 14.641 2.138 1.00 0.00 <br />
ATOM 14 C14 MOL 1 17.546 12.770 0.237 1.00 0.00 <br />
ATOM 15 C15 MOL 1 17.644 14.930 -0.793 1.00 0.00 <br />
ATOM 16 C16 MOL 1 19.772 16.333 -0.179 1.00 0.00 <br />
ATOM 17 C17 MOL 1 18.538 16.078 2.002 1.00 0.00 <br />
ATOM 18 C18 MOL 1 16.298 12.542 -0.183 1.00 0.00 <br />
ATOM 19 C19 MOL 1 18.462 16.189 -1.090 1.00 0.00 <br />
ATOM 20 C20 MOL 1 16.318 14.720 -1.345 1.00 0.00 <br />
ATOM 21 N21 MOL 1 19.493 16.889 1.202 1.00 0.00 <br />
ATOM 22 O22 MOL 1 15.642 11.319 0.166 1.00 0.00 <br />
ATOM 23 C23 MOL 1 15.656 13.605 -1.022 1.00 0.00 <br />
ATOM 24 C24 MOL 1 18.950 18.247 1.075 1.00 0.00 <br />
ATOM 25 C25 MOL 1 14.263 11.150 -0.231 1.00 0.00 <br />
ATOM 26 C26 MOL 1 13.567 9.867 0.115 1.00 0.00 <br />
ATOM 27 O27 MOL 1 13.607 12.019 -0.820 1.00 0.00 <br />
ATOM 28 H28 MOL 1 21.358 14.995 0.556 1.00 0.00 <br />
ATOM 29 H29 MOL 1 20.362 12.366 1.900 1.00 0.00 <br />
ATOM 30 H30 MOL 1 20.458 17.021 -0.692 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br><br />
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br><br />
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.<br />
<br />
<br><br />
<br />
==Synthesis of Codeine from Morphine==<br />
[[Image:codeine_s.gif|thumb|Synthesis of Codeine]]<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]<br />
*Schmitz J, Stotts A, Rhoades H, Grabowski J. "Naltrexone and relapse prevention treatment for cocaine-dependent patients.". Addict Behav 26 (2): 167-80. PMID 11316375. <br />
*Chicago Recovery Alliance's naloxone distrobution project<br />
*Synthesis of codeine from morphine. Ai, Lin; Chen, Xiaoyuan; Zhang, Le. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005)</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=4313
It:Gentamycin
2006-10-26T14:18:24Z
<p>Ffs05: edite property table</p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against [[Gram]] negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial [[ribosome]]. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
==Before taking Gentamycin,==<br />
<br />
Talk to your doctor if you have sulfite sensitivity, kidney disease, hearing loss or loss of balance due to ear problems, Parkinson's disease, or a neuromuscular disorder such as myasthenia gravis. You may not be able to use gentamicin, or you may require a dosage adjustment or special monitoring during treatment if you have any of the conditions listed above.<br />
<br />
Do not take any other medicines, including vitamins, minerals, and herbal products, without first talking to your doctor during treatment with gentamycin <br />
<br />
There are no restrictions on food, beverages, or activity while taking gentamycin unless otherwise directed by your doctor.<br />
<br />
[http://www.lawyersandsettlements.com/articles/gentamycin_balance.html Article: 'The Dangers of Gentamycin' by Jane Mundy, December 18, 2005. ]<br />
<br />
==Side Effects==<br />
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).<br />
<br />
In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:<br />
*deafness<br />
<br />
The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.<br />
<br />
*loss of equilibrium<br />
<br />
The reason for this is that the gentamysin can cause significant damage to a patient’s vestibular system, which is part of the inner ear responsible for <br />
maintaining balance, sense of body position, visual focus, coordination, and orientation. Gentamicin can seriously damage the tiny hairs of the inner ears (responsible for sense of gravity, sense of motion, and providing information to the brain), causing serious hearing problems and visuo-spacial problems.<br />
<br />
In addition, Unfortunately, there is no cure for gentamicin hearing problems or vestibular damage. Patients may recover, but the process is very slow and not often complete. The brain may be able to adapt and compensate for information no longer received from the inner ear by relying on other senses for input. Vestibular Rehabilitation, designed to stimulate the partially damaged system, may also be beneficial. Early diagnosis of gentamicin hearing damage is essential to maximizing a patient’s prognosis. Diagnosis is made by thorough physical examination, special testing, and taking a full medical history.<br />
<br />
==Symptoms of overdose ==<br />
<br />
*damage to the kidneys<br />
<br />
*hearing loss<br />
<br />
*dizziness<br />
<br />
*numbness<br />
<br />
*skin tingling<br />
<br />
*muscle twitching<br />
<br />
*seizures (which may be signs of nerve damage)<br />
<br />
*Trouble walking or balancing<br />
<br />
*The symptoms of gentamicin poisoning often persist after leaving the hospital, can also include mental confusion, extreme fatigue, and diminished short-term memory. These symptoms of serious gentamicin side effects may be difficult to detect in a child.<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00 <br />
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00 <br />
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00 <br />
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00 <br />
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00 <br />
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00 <br />
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00 <br />
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00 <br />
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00 <br />
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00 <br />
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00 <br />
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
68 70 0 0 0 0 0 0 0 0999 V2000<br />
-4.8690 -0.2540 2.7230 O 0 0 0 0 0 0 0 0 0 1<br />
-4.8110 0.9570 1.9660 C 0 0 0 0 0 0 0 0 0 2<br />
-4.2080 0.6690 0.5900 C 0 0 1 0 0 0 0 0 0 3<br />
-4.2610 1.9380 -0.2640 C 0 0 2 0 0 0 0 0 0 4<br />
-3.4860 2.9650 0.3570 O 0 0 0 0 0 0 0 0 0 5<br />
-3.6860 1.6300 -1.6520 C 0 0 1 0 0 0 0 0 0 6<br />
-3.5880 2.8380 -2.4090 O 0 0 0 0 0 0 0 0 0 7<br />
-2.2910 1.0170 -1.4800 C 0 0 1 0 0 0 0 0 0 8<br />
-1.3800 2.0190 -0.9120 N 0 0 0 0 0 0 0 0 0 9<br />
-2.3880 -0.1830 -0.5340 C 0 0 1 0 0 0 0 0 0 10<br />
-1.0970 -0.7810 -0.3920 O 0 0 0 0 0 0 0 0 0 11<br />
-1.2960 -2.0440 0.2460 C 0 0 1 0 0 0 0 0 0 12<br />
-1.3100 -3.1520 -0.8090 C 0 0 1 0 0 0 0 0 0 13<br />
-2.4010 -2.9070 -1.7610 N 0 0 0 0 0 0 0 0 0 14<br />
0.0260 -3.1610 -1.5560 C 0 0 0 0 0 0 0 0 0 15<br />
1.1630 -3.4160 -0.5650 C 0 0 2 0 0 0 0 0 0 16<br />
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1.1770 -2.3080 0.4900 C 0 0 1 0 0 0 0 0 0 18<br />
1.3750 -1.0450 -0.1480 O 0 0 0 0 0 0 0 0 0 19<br />
2.6860 -0.6020 0.2110 C 0 0 1 0 0 0 0 0 0 20<br />
3.0880 0.5730 -0.6830 C 0 0 2 0 0 0 0 0 0 21<br />
2.1790 1.6580 -0.4840 O 0 0 0 0 0 0 0 0 0 22<br />
4.5070 1.0190 -0.3140 C 0 0 2 0 0 0 0 0 0 23<br />
4.8480 2.2420 -1.0540 N 0 0 0 0 0 0 0 0 0 24<br />
6.3130 2.2790 -1.1560 C 0 0 0 0 0 0 0 0 0 25<br />
4.5570 1.2980 1.1920 C 0 0 2 0 0 0 0 0 0 26<br />
3.7320 2.4240 1.4980 O 0 0 0 0 0 0 0 0 0 27<br />
4.0440 0.0680 1.9440 C 0 0 0 0 0 0 0 0 0 28<br />
2.6910 -0.1930 1.5770 O 0 0 0 0 0 0 0 0 0 29<br />
-0.1580 -2.2980 1.2370 C 0 0 2 0 0 0 0 0 0 30<br />
-0.1450 -1.2630 2.2230 O 0 0 0 0 0 0 0 0 0 31<br />
-2.8540 0.2460 0.7440 O 0 0 0 0 0 0 0 0 0 32<br />
-5.2540 -0.0280 3.5810 H 0 0 0 0 0 0 0 0 0 33<br />
-5.8170 1.3580 1.8450 H 0 0 0 0 0 0 0 0 0 34<br />
-4.1900 1.6840 2.4900 H 0 0 0 0 0 0 0 0 0 35<br />
-4.7790 -0.1210 0.1020 H 0 0 0 0 0 0 0 0 0 36<br />
-5.2940 2.2690 -0.3620 H 0 0 0 0 0 0 0 0 0 37<br />
-3.9350 3.1930 1.1830 H 0 0 0 0 0 0 0 0 0 38<br />
-4.3370 0.9260 -2.1690 H 0 0 0 0 0 0 0 0 0 39<br />
-4.4830 3.1960 -2.4810 H 0 0 0 0 0 0 0 0 0 40<br />
-1.9150 0.6890 -2.4490 H 0 0 0 0 0 0 0 0 0 41<br />
-0.4630 1.5980 -0.8890 H 0 0 0 0 0 0 0 0 0 42<br />
-1.3340 2.7780 -1.5750 H 0 0 0 0 0 0 0 0 0 43<br />
-3.0830 -0.9140 -0.9450 H 0 0 0 0 0 0 0 0 0 44<br />
-2.2470 -2.0370 0.7780 H 0 0 0 0 0 0 0 0 0 45<br />
-1.4610 -4.1150 -0.3220 H 0 0 0 0 0 0 0 0 0 46<br />
-2.3720 -3.6580 -2.4340 H 0 0 0 0 0 0 0 0 0 47<br />
-3.2630 -3.0120 -1.2470 H 0 0 0 0 0 0 0 0 0 48<br />
0.0160 -3.9510 -2.3080 H 0 0 0 0 0 0 0 0 0 49<br />
0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50<br />
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51<br />
2.4310 -4.2300 -1.8900 H 0 0 0 0 0 0 0 0 0 52<br />
2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53<br />
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54<br />
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55<br />
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56<br />
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57<br />
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58<br />
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59<br />
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60<br />
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61<br />
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62<br />
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63<br />
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64<br />
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65<br />
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66<br />
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67<br />
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68<br />
1 2 1 0 0 0<br />
1 33 1 0 0 0<br />
5 4 1 0 0 0<br />
5 38 1 0 0 0<br />
7 6 1 0 0 0<br />
7 40 1 0 0 0<br />
9 8 1 0 0 0<br />
9 42 1 0 0 0<br />
9 43 1 0 0 0<br />
11 10 1 0 0 0<br />
11 12 1 0 0 0<br />
14 13 1 0 0 0<br />
14 47 1 0 0 0<br />
14 48 1 0 0 0<br />
17 16 1 0 0 0<br />
17 52 1 0 0 0<br />
17 53 1 0 0 0<br />
19 18 1 0 0 0<br />
19 20 1 0 0 0<br />
22 21 1 0 0 0<br />
22 57 1 0 0 0<br />
24 23 1 0 0 0<br />
24 25 1 0 0 0<br />
24 59 1 0 0 0<br />
27 26 1 0 0 0<br />
27 64 1 0 0 0<br />
29 28 1 0 0 0<br />
29 20 1 0 0 0<br />
31 30 1 0 0 0<br />
31 68 1 0 0 0<br />
32 10 1 0 0 0<br />
32 3 1 0 0 0<br />
2 35 1 0 0 0<br />
2 34 1 0 0 0<br />
2 3 1 0 0 0<br />
3 36 1 0 0 0<br />
3 4 1 0 0 0<br />
4 37 1 0 0 0<br />
4 6 1 0 0 0<br />
6 8 1 0 0 0<br />
6 39 1 0 0 0<br />
8 10 1 0 0 0<br />
8 41 1 0 0 0<br />
10 44 1 0 0 0<br />
12 30 1 0 0 0<br />
12 45 1 0 0 0<br />
12 13 1 0 0 0<br />
13 15 1 0 0 0<br />
13 46 1 0 0 0<br />
15 16 1 0 0 0<br />
15 50 1 0 0 0<br />
15 49 1 0 0 0<br />
16 51 1 0 0 0<br />
16 18 1 0 0 0<br />
18 30 1 0 0 0<br />
18 54 1 0 0 0<br />
20 55 1 0 0 0<br />
20 21 1 0 0 0<br />
21 56 1 0 0 0<br />
21 23 1 0 0 0<br />
23 58 1 0 0 0<br />
23 26 1 0 0 0<br />
25 60 1 0 0 0<br />
25 61 1 0 0 0<br />
25 62 1 0 0 0<br />
26 63 1 0 0 0<br />
26 28 1 0 0 0<br />
28 66 1 0 0 0<br />
28 65 1 0 0 0<br />
30 67 1 0 0 0<br />
M END<br />
<br />
<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
== Properties of Gentamycin ==<br />
<br />
'''Physical propertites'''<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General'''<br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| solubility in water<br />
| align="center"| 100mg/mL<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| CA Index Name<br />
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
|-<br />
|CAS Registry Number<br />
| align="center"| 13291-74-2<br />
|-<br />
|}<br />
'''Pharmacokinetic properties'''<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| Toxicity<br />
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.<br />
|- <br />
| Protein bonding<br />
| align="left"|Low (between 0 and 30%)<br />
|-<br />
| Half life<br />
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.<br />
|-<br />
| Dosage form<br />
| align="left"|Cream Drops Liquid Ointment Solution <br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
*Sci Finder, Registry Number: 13291-74-2<br />
*http://en.wikipedia.org/wiki/Gentamicin</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=4247
It:Morphine
2006-10-26T13:50:33Z
<p>Ffs05: /* Pharmacology of Morphine */</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
== Properties of Morphine ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data''' <br />
|-<br />
| IUPAC Name<br />
| align="center"|7,8-didehydro-<br />
4,5-epoxy-17-methylmorphinan-3,6-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub><br />
|-<br />
| Molar Mass<br />
| align="center"|285.4 g/mol<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''<br />
|-<br />
| Bioavailability<br />
| align="center"|... ~30%<br />
|-<br />
| Protein binding<br />
| align="center"|... 30–40%<br />
|-<br />
| Metabolism<br />
| align="center"|... Hepatic 90%<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''<br />
|-<br />
| Pregnancy cat.<br />
| align="center"| C(AU) C(US)<br />
|-<br />
| Legal status<br />
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only<br />
|-<br />
| Dependence Liability<br />
| align="center"| Extremely High<br />
|-<br />
| Routes<br />
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
<br />
<br />
==Pharmacology of Morphine==<br />
<br />
Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:48:06 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 18.255 13.156 0.573 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.569 14.167 -0.163 1.00 0.00 <br />
ATOM 3 C3 MOL 1 16.417 14.732 0.663 1.00 0.00 <br />
ATOM 4 C4 MOL 1 18.496 15.366 -0.471 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.015 13.567 -1.482 1.00 0.00 <br />
ATOM 6 C6 MOL 1 15.693 15.779 0.018 1.00 0.00 <br />
ATOM 7 C7 MOL 1 15.307 13.777 1.020 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.942 15.313 2.010 1.00 0.00 <br />
ATOM 9 C9 MOL 1 17.646 16.451 -1.361 1.00 0.00 <br />
ATOM 10 N10 MOL 1 19.019 15.899 0.861 1.00 0.00 <br />
ATOM 11 C11 MOL 1 15.959 12.473 -1.196 1.00 0.00 <br />
ATOM 12 C12 MOL 1 14.403 15.799 0.518 1.00 0.00 <br />
ATOM 13 C13 MOL 1 16.179 16.645 -0.862 1.00 0.00 <br />
ATOM 14 O14 MOL 1 14.159 14.689 1.403 1.00 0.00 <br />
ATOM 15 C15 MOL 1 14.899 12.986 -0.210 1.00 0.00 <br />
ATOM 16 C16 MOL 1 17.969 16.420 1.747 1.00 0.00 <br />
ATOM 17 C17 MOL 1 20.056 16.927 0.663 1.00 0.00 <br />
ATOM 18 C18 MOL 1 13.566 16.775 0.184 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.281 17.721 -1.321 1.00 0.00 <br />
ATOM 20 O20 MOL 1 13.720 12.646 -0.346 1.00 0.00 <br />
ATOM 21 C21 MOL 1 21.259 16.286 0.008 1.00 0.00 <br />
ATOM 22 O22 MOL 1 12.278 16.816 0.702 1.00 0.00 <br />
ATOM 23 C23 MOL 1 14.040 17.798 -0.803 1.00 0.00 <br />
ATOM 24 C24 MOL 1 22.410 16.944 -0.094 1.00 0.00 <br />
ATOM 25 H25 MOL 1 19.357 15.031 -1.060 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:49:10 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 17.558 13.998 -0.496 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.076 15.115 0.248 1.00 0.00 <br />
ATOM 3 C3 MOL 1 17.258 16.394 -0.557 1.00 0.00 <br />
ATOM 4 C4 MOL 1 15.561 15.011 0.531 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.860 15.228 1.589 1.00 0.00 <br />
ATOM 6 C6 MOL 1 16.778 17.574 0.073 1.00 0.00 <br />
ATOM 7 C7 MOL 1 18.653 16.799 -0.879 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.508 16.294 -1.921 1.00 0.00 <br />
ATOM 9 C9 MOL 1 15.127 16.315 1.434 1.00 0.00 <br />
ATOM 10 N10 MOL 1 14.843 14.899 -0.812 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.354 15.543 1.336 1.00 0.00 <br />
ATOM 12 C12 MOL 1 17.493 18.660 -0.426 1.00 0.00 <br />
ATOM 13 C13 MOL 1 15.791 17.648 0.954 1.00 0.00 <br />
ATOM 14 O14 MOL 1 18.548 18.231 -1.333 1.00 0.00 <br />
ATOM 15 C15 MOL 1 19.467 16.754 0.400 1.00 0.00 <br />
ATOM 16 C16 MOL 1 15.014 16.064 -1.686 1.00 0.00 <br />
ATOM 17 C17 MOL 1 13.406 14.609 -0.651 1.00 0.00 <br />
ATOM 18 C18 MOL 1 17.129 19.900 -0.114 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.387 18.995 1.400 1.00 0.00 <br />
ATOM 20 O20 MOL 1 20.317 17.624 0.613 1.00 0.00 <br />
ATOM 21 C21 MOL 1 13.178 13.073 -0.836 1.00 0.00 <br />
ATOM 22 O22 MOL 1 17.801 20.995 -0.638 1.00 0.00 <br />
ATOM 23 C23 MOL 1 16.014 20.069 0.881 1.00 0.00 <br />
ATOM 24 C24 MOL 1 11.870 12.702 -0.129 1.00 0.00 <br />
ATOM 25 C25 MOL 1 13.234 12.318 0.500 1.00 0.00 <br />
ATOM 26 H26 MOL 1 19.132 16.101 -1.579 1.00 0.00 <br />
ATOM 27 H27 MOL 1 15.339 14.101 1.101 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Naloxone<br />
|Naltrexone<br />
|-<br />
|}<br />
<br />
<br />
<br />
Both naloxone and naltrexone are competitive antagonists at the μ- and κ-opioid receptors, and to a lesser extent at δ-opioid receptors. The blockade of these receptors is what prevents the opiods such as morphine, from combining with these receptor sites thus preventing the side effects usually caused by morphine.<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroin<br />
|-<br />
|align="left" colspan="3" bgcolor="white"| <br />
|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 14:36:49 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.380 10.913 -0.058 1.00 0.00 <br />
ATOM 2 C2 MOL 1 22.712 10.864 -0.568 1.00 0.00 <br />
ATOM 3 C3 MOL 1 20.932 12.266 -0.071 1.00 0.00 <br />
ATOM 4 C4 MOL 1 23.445 9.558 -0.647 1.00 0.00 <br />
ATOM 5 O5 MOL 1 23.307 11.901 -0.901 1.00 0.00 <br />
ATOM 6 C6 MOL 1 19.783 12.581 0.994 1.00 0.00 <br />
ATOM 7 C7 MOL 1 20.757 12.864 -1.427 1.00 0.00 <br />
ATOM 8 C8 MOL 1 19.419 14.067 0.744 1.00 0.00 <br />
ATOM 9 O9 MOL 1 18.395 11.892 1.004 1.00 0.00 <br />
ATOM 10 C10 MOL 1 20.623 14.207 -1.407 1.00 0.00 <br />
ATOM 11 C11 MOL 1 18.168 13.977 -0.025 1.00 0.00 <br />
ATOM 12 C12 MOL 1 20.420 14.937 -0.012 1.00 0.00 <br />
ATOM 13 C13 MOL 1 19.051 14.641 2.138 1.00 0.00 <br />
ATOM 14 C14 MOL 1 17.546 12.770 0.237 1.00 0.00 <br />
ATOM 15 C15 MOL 1 17.644 14.930 -0.793 1.00 0.00 <br />
ATOM 16 C16 MOL 1 19.772 16.333 -0.179 1.00 0.00 <br />
ATOM 17 C17 MOL 1 18.538 16.078 2.002 1.00 0.00 <br />
ATOM 18 C18 MOL 1 16.298 12.542 -0.183 1.00 0.00 <br />
ATOM 19 C19 MOL 1 18.462 16.189 -1.090 1.00 0.00 <br />
ATOM 20 C20 MOL 1 16.318 14.720 -1.345 1.00 0.00 <br />
ATOM 21 N21 MOL 1 19.493 16.889 1.202 1.00 0.00 <br />
ATOM 22 O22 MOL 1 15.642 11.319 0.166 1.00 0.00 <br />
ATOM 23 C23 MOL 1 15.656 13.605 -1.022 1.00 0.00 <br />
ATOM 24 C24 MOL 1 18.950 18.247 1.075 1.00 0.00 <br />
ATOM 25 C25 MOL 1 14.263 11.150 -0.231 1.00 0.00 <br />
ATOM 26 C26 MOL 1 13.567 9.867 0.115 1.00 0.00 <br />
ATOM 27 O27 MOL 1 13.607 12.019 -0.820 1.00 0.00 <br />
ATOM 28 H28 MOL 1 21.358 14.995 0.556 1.00 0.00 <br />
ATOM 29 H29 MOL 1 20.362 12.366 1.900 1.00 0.00 <br />
ATOM 30 H30 MOL 1 20.458 17.021 -0.692 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 14:36:05 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 12.755 17.484 0.278 1.00 0.00 <br />
ATOM 2 C2 MOL 1 14.165 17.279 0.259 1.00 0.00 <br />
ATOM 3 C3 MOL 1 14.598 16.294 -0.907 1.00 0.00 <br />
ATOM 4 C4 MOL 1 14.783 17.091 1.590 1.00 0.00 <br />
ATOM 5 C5 MOL 1 16.085 15.955 -0.655 1.00 0.00 <br />
ATOM 6 O6 MOL 1 13.944 14.927 -0.976 1.00 0.00 <br />
ATOM 7 C7 MOL 1 16.137 17.074 1.556 1.00 0.00 <br />
ATOM 8 C8 MOL 1 15.986 14.685 0.099 1.00 0.00 <br />
ATOM 9 C9 MOL 1 16.902 16.950 0.154 1.00 0.00 <br />
ATOM 10 C10 MOL 1 16.709 15.628 -2.040 1.00 0.00 <br />
ATOM 11 C11 MOL 1 14.759 14.077 -0.164 1.00 0.00 <br />
ATOM 12 C12 MOL 1 16.917 14.157 0.888 1.00 0.00 <br />
ATOM 13 C13 MOL 1 18.319 16.318 0.340 1.00 0.00 <br />
ATOM 14 C14 MOL 1 18.152 15.134 -1.868 1.00 0.00 <br />
ATOM 15 C15 MOL 1 14.483 12.853 0.325 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.177 14.972 1.210 1.00 0.00 <br />
ATOM 17 C17 MOL 1 16.666 12.844 1.470 1.00 0.00 <br />
ATOM 18 N18 MOL 1 18.922 16.087 -1.029 1.00 0.00 <br />
ATOM 19 O19 MOL 1 13.263 12.126 0.120 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.521 12.211 1.182 1.00 0.00 <br />
ATOM 21 C21 MOL 1 20.289 15.567 -0.871 1.00 0.00 <br />
ATOM 22 C22 MOL 1 12.251 12.761 -0.671 1.00 0.00 <br />
ATOM 23 H23 MOL 1 16.955 17.909 -0.379 1.00 0.00 <br />
ATOM 24 H24 MOL 1 14.357 16.925 -1.773 1.00 0.00 <br />
ATOM 25 H25 MOL 1 18.981 17.000 0.892 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br><br />
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br><br />
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.<br />
<br />
<br><br />
<br />
<br />
==Synthesis of Codeine from Morphine==<br />
[[Image:codeine_s.gif|thumb|Synthesis of Codeine]]<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]<br />
*Schmitz J, Stotts A, Rhoades H, Grabowski J. "Naltrexone and relapse prevention treatment for cocaine-dependent patients.". Addict Behav 26 (2): 167-80. PMID 11316375. <br />
*Chicago Recovery Alliance's naloxone distrobution project<br />
*Synthesis of codeine from morphine. Ai, Lin; Chen, Xiaoyuan; Zhang, Le. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005)</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=4245
It:Morphine
2006-10-26T13:49:58Z
<p>Ffs05: added 3d structures of codeine and heroin</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
== Properties of Morphine ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data''' <br />
|-<br />
| IUPAC Name<br />
| align="center"|7,8-didehydro-<br />
4,5-epoxy-17-methylmorphinan-3,6-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub><br />
|-<br />
| Molar Mass<br />
| align="center"|285.4 g/mol<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''<br />
|-<br />
| Bioavailability<br />
| align="center"|... ~30%<br />
|-<br />
| Protein binding<br />
| align="center"|... 30–40%<br />
|-<br />
| Metabolism<br />
| align="center"|... Hepatic 90%<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''<br />
|-<br />
| Pregnancy cat.<br />
| align="center"| C(AU) C(US)<br />
|-<br />
| Legal status<br />
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only<br />
|-<br />
| Dependence Liability<br />
| align="center"| Extremely High<br />
|-<br />
| Routes<br />
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
<br />
<br />
==Pharmacology of Morphine==<br />
<br />
Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:48:06 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 18.255 13.156 0.573 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.569 14.167 -0.163 1.00 0.00 <br />
ATOM 3 C3 MOL 1 16.417 14.732 0.663 1.00 0.00 <br />
ATOM 4 C4 MOL 1 18.496 15.366 -0.471 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.015 13.567 -1.482 1.00 0.00 <br />
ATOM 6 C6 MOL 1 15.693 15.779 0.018 1.00 0.00 <br />
ATOM 7 C7 MOL 1 15.307 13.777 1.020 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.942 15.313 2.010 1.00 0.00 <br />
ATOM 9 C9 MOL 1 17.646 16.451 -1.361 1.00 0.00 <br />
ATOM 10 N10 MOL 1 19.019 15.899 0.861 1.00 0.00 <br />
ATOM 11 C11 MOL 1 15.959 12.473 -1.196 1.00 0.00 <br />
ATOM 12 C12 MOL 1 14.403 15.799 0.518 1.00 0.00 <br />
ATOM 13 C13 MOL 1 16.179 16.645 -0.862 1.00 0.00 <br />
ATOM 14 O14 MOL 1 14.159 14.689 1.403 1.00 0.00 <br />
ATOM 15 C15 MOL 1 14.899 12.986 -0.210 1.00 0.00 <br />
ATOM 16 C16 MOL 1 17.969 16.420 1.747 1.00 0.00 <br />
ATOM 17 C17 MOL 1 20.056 16.927 0.663 1.00 0.00 <br />
ATOM 18 C18 MOL 1 13.566 16.775 0.184 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.281 17.721 -1.321 1.00 0.00 <br />
ATOM 20 O20 MOL 1 13.720 12.646 -0.346 1.00 0.00 <br />
ATOM 21 C21 MOL 1 21.259 16.286 0.008 1.00 0.00 <br />
ATOM 22 O22 MOL 1 12.278 16.816 0.702 1.00 0.00 <br />
ATOM 23 C23 MOL 1 14.040 17.798 -0.803 1.00 0.00 <br />
ATOM 24 C24 MOL 1 22.410 16.944 -0.094 1.00 0.00 <br />
ATOM 25 H25 MOL 1 19.357 15.031 -1.060 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:49:10 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 17.558 13.998 -0.496 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.076 15.115 0.248 1.00 0.00 <br />
ATOM 3 C3 MOL 1 17.258 16.394 -0.557 1.00 0.00 <br />
ATOM 4 C4 MOL 1 15.561 15.011 0.531 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.860 15.228 1.589 1.00 0.00 <br />
ATOM 6 C6 MOL 1 16.778 17.574 0.073 1.00 0.00 <br />
ATOM 7 C7 MOL 1 18.653 16.799 -0.879 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.508 16.294 -1.921 1.00 0.00 <br />
ATOM 9 C9 MOL 1 15.127 16.315 1.434 1.00 0.00 <br />
ATOM 10 N10 MOL 1 14.843 14.899 -0.812 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.354 15.543 1.336 1.00 0.00 <br />
ATOM 12 C12 MOL 1 17.493 18.660 -0.426 1.00 0.00 <br />
ATOM 13 C13 MOL 1 15.791 17.648 0.954 1.00 0.00 <br />
ATOM 14 O14 MOL 1 18.548 18.231 -1.333 1.00 0.00 <br />
ATOM 15 C15 MOL 1 19.467 16.754 0.400 1.00 0.00 <br />
ATOM 16 C16 MOL 1 15.014 16.064 -1.686 1.00 0.00 <br />
ATOM 17 C17 MOL 1 13.406 14.609 -0.651 1.00 0.00 <br />
ATOM 18 C18 MOL 1 17.129 19.900 -0.114 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.387 18.995 1.400 1.00 0.00 <br />
ATOM 20 O20 MOL 1 20.317 17.624 0.613 1.00 0.00 <br />
ATOM 21 C21 MOL 1 13.178 13.073 -0.836 1.00 0.00 <br />
ATOM 22 O22 MOL 1 17.801 20.995 -0.638 1.00 0.00 <br />
ATOM 23 C23 MOL 1 16.014 20.069 0.881 1.00 0.00 <br />
ATOM 24 C24 MOL 1 11.870 12.702 -0.129 1.00 0.00 <br />
ATOM 25 C25 MOL 1 13.234 12.318 0.500 1.00 0.00 <br />
ATOM 26 H26 MOL 1 19.132 16.101 -1.579 1.00 0.00 <br />
ATOM 27 H27 MOL 1 15.339 14.101 1.101 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Naloxone<br />
|Naltrexone<br />
|-<br />
|}<br />
<br />
<br />
<br />
Both naloxone and naltrexone are competitive antagonists at the μ- and κ-opioid receptors, and to a lesser extent at δ-opioid receptors. The blockade of these receptors is what prevents the opiods such as morphine, from combining with these receptor sites thus preventing the side effects usually caused by morphine.<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroin<br />
|-<br />
|align="left" colspan="3" bgcolor="white"| <br />
|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 14:36:49 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.380 10.913 -0.058 1.00 0.00 <br />
ATOM 2 C2 MOL 1 22.712 10.864 -0.568 1.00 0.00 <br />
ATOM 3 C3 MOL 1 20.932 12.266 -0.071 1.00 0.00 <br />
ATOM 4 C4 MOL 1 23.445 9.558 -0.647 1.00 0.00 <br />
ATOM 5 O5 MOL 1 23.307 11.901 -0.901 1.00 0.00 <br />
ATOM 6 C6 MOL 1 19.783 12.581 0.994 1.00 0.00 <br />
ATOM 7 C7 MOL 1 20.757 12.864 -1.427 1.00 0.00 <br />
ATOM 8 C8 MOL 1 19.419 14.067 0.744 1.00 0.00 <br />
ATOM 9 O9 MOL 1 18.395 11.892 1.004 1.00 0.00 <br />
ATOM 10 C10 MOL 1 20.623 14.207 -1.407 1.00 0.00 <br />
ATOM 11 C11 MOL 1 18.168 13.977 -0.025 1.00 0.00 <br />
ATOM 12 C12 MOL 1 20.420 14.937 -0.012 1.00 0.00 <br />
ATOM 13 C13 MOL 1 19.051 14.641 2.138 1.00 0.00 <br />
ATOM 14 C14 MOL 1 17.546 12.770 0.237 1.00 0.00 <br />
ATOM 15 C15 MOL 1 17.644 14.930 -0.793 1.00 0.00 <br />
ATOM 16 C16 MOL 1 19.772 16.333 -0.179 1.00 0.00 <br />
ATOM 17 C17 MOL 1 18.538 16.078 2.002 1.00 0.00 <br />
ATOM 18 C18 MOL 1 16.298 12.542 -0.183 1.00 0.00 <br />
ATOM 19 C19 MOL 1 18.462 16.189 -1.090 1.00 0.00 <br />
ATOM 20 C20 MOL 1 16.318 14.720 -1.345 1.00 0.00 <br />
ATOM 21 N21 MOL 1 19.493 16.889 1.202 1.00 0.00 <br />
ATOM 22 O22 MOL 1 15.642 11.319 0.166 1.00 0.00 <br />
ATOM 23 C23 MOL 1 15.656 13.605 -1.022 1.00 0.00 <br />
ATOM 24 C24 MOL 1 18.950 18.247 1.075 1.00 0.00 <br />
ATOM 25 C25 MOL 1 14.263 11.150 -0.231 1.00 0.00 <br />
ATOM 26 C26 MOL 1 13.567 9.867 0.115 1.00 0.00 <br />
ATOM 27 O27 MOL 1 13.607 12.019 -0.820 1.00 0.00 <br />
ATOM 28 H28 MOL 1 21.358 14.995 0.556 1.00 0.00 <br />
ATOM 29 H29 MOL 1 20.362 12.366 1.900 1.00 0.00 <br />
ATOM 30 H30 MOL 1 20.458 17.021 -0.692 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents><br />
REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 14:36:05 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 12.755 17.484 0.278 1.00 0.00 <br />
ATOM 2 C2 MOL 1 14.165 17.279 0.259 1.00 0.00 <br />
ATOM 3 C3 MOL 1 14.598 16.294 -0.907 1.00 0.00 <br />
ATOM 4 C4 MOL 1 14.783 17.091 1.590 1.00 0.00 <br />
ATOM 5 C5 MOL 1 16.085 15.955 -0.655 1.00 0.00 <br />
ATOM 6 O6 MOL 1 13.944 14.927 -0.976 1.00 0.00 <br />
ATOM 7 C7 MOL 1 16.137 17.074 1.556 1.00 0.00 <br />
ATOM 8 C8 MOL 1 15.986 14.685 0.099 1.00 0.00 <br />
ATOM 9 C9 MOL 1 16.902 16.950 0.154 1.00 0.00 <br />
ATOM 10 C10 MOL 1 16.709 15.628 -2.040 1.00 0.00 <br />
ATOM 11 C11 MOL 1 14.759 14.077 -0.164 1.00 0.00 <br />
ATOM 12 C12 MOL 1 16.917 14.157 0.888 1.00 0.00 <br />
ATOM 13 C13 MOL 1 18.319 16.318 0.340 1.00 0.00 <br />
ATOM 14 C14 MOL 1 18.152 15.134 -1.868 1.00 0.00 <br />
ATOM 15 C15 MOL 1 14.483 12.853 0.325 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.177 14.972 1.210 1.00 0.00 <br />
ATOM 17 C17 MOL 1 16.666 12.844 1.470 1.00 0.00 <br />
ATOM 18 N18 MOL 1 18.922 16.087 -1.029 1.00 0.00 <br />
ATOM 19 O19 MOL 1 13.263 12.126 0.120 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.521 12.211 1.182 1.00 0.00 <br />
ATOM 21 C21 MOL 1 20.289 15.567 -0.871 1.00 0.00 <br />
ATOM 22 C22 MOL 1 12.251 12.761 -0.671 1.00 0.00 <br />
ATOM 23 H23 MOL 1 16.955 17.909 -0.379 1.00 0.00 <br />
ATOM 24 H24 MOL 1 14.357 16.925 -1.773 1.00 0.00 <br />
ATOM 25 H25 MOL 1 18.981 17.000 0.892 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br><br />
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br><br />
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.<br />
<br />
<br><br />
<br />
<br />
==Synthesis of Codeine from Morphine==<br />
[[Image:codeine_s.gif|thumb|Synthesis of Codeine]]<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]<br />
*Schmitz J, Stotts A, Rhoades H, Grabowski J. "Naltrexone and relapse prevention treatment for cocaine-dependent patients.". Addict Behav 26 (2): 167-80. PMID 11316375. <br />
*Chicago Recovery Alliance's naloxone distrobution project<br />
*Synthesis of codeine from morphine. Ai, Lin; Chen, Xiaoyuan; Zhang, Le. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005)</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=4200
It:Morphine
2006-10-26T13:10:20Z
<p>Ffs05: added reference</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
== Properties of Morphine ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data''' <br />
|-<br />
| IUPAC Name<br />
| align="center"|7,8-didehydro-<br />
4,5-epoxy-17-methylmorphinan-3,6-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub><br />
|-<br />
| Molar Mass<br />
| align="center"|285.4 g/mol<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''<br />
|-<br />
| Bioavailability<br />
| align="center"|... ~30%<br />
|-<br />
| Protein binding<br />
| align="center"|... 30–40%<br />
|-<br />
| Metabolism<br />
| align="center"|... Hepatic 90%<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''<br />
|-<br />
| Pregnancy cat.<br />
| align="center"| C(AU) C(US)<br />
|-<br />
| Legal status<br />
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only<br />
|-<br />
| Dependence Liability<br />
| align="center"| Extremely High<br />
|-<br />
| Routes<br />
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
<br />
<br />
==Pharmacology of Morphine==<br />
<br />
Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:48:06 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 18.255 13.156 0.573 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.569 14.167 -0.163 1.00 0.00 <br />
ATOM 3 C3 MOL 1 16.417 14.732 0.663 1.00 0.00 <br />
ATOM 4 C4 MOL 1 18.496 15.366 -0.471 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.015 13.567 -1.482 1.00 0.00 <br />
ATOM 6 C6 MOL 1 15.693 15.779 0.018 1.00 0.00 <br />
ATOM 7 C7 MOL 1 15.307 13.777 1.020 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.942 15.313 2.010 1.00 0.00 <br />
ATOM 9 C9 MOL 1 17.646 16.451 -1.361 1.00 0.00 <br />
ATOM 10 N10 MOL 1 19.019 15.899 0.861 1.00 0.00 <br />
ATOM 11 C11 MOL 1 15.959 12.473 -1.196 1.00 0.00 <br />
ATOM 12 C12 MOL 1 14.403 15.799 0.518 1.00 0.00 <br />
ATOM 13 C13 MOL 1 16.179 16.645 -0.862 1.00 0.00 <br />
ATOM 14 O14 MOL 1 14.159 14.689 1.403 1.00 0.00 <br />
ATOM 15 C15 MOL 1 14.899 12.986 -0.210 1.00 0.00 <br />
ATOM 16 C16 MOL 1 17.969 16.420 1.747 1.00 0.00 <br />
ATOM 17 C17 MOL 1 20.056 16.927 0.663 1.00 0.00 <br />
ATOM 18 C18 MOL 1 13.566 16.775 0.184 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.281 17.721 -1.321 1.00 0.00 <br />
ATOM 20 O20 MOL 1 13.720 12.646 -0.346 1.00 0.00 <br />
ATOM 21 C21 MOL 1 21.259 16.286 0.008 1.00 0.00 <br />
ATOM 22 O22 MOL 1 12.278 16.816 0.702 1.00 0.00 <br />
ATOM 23 C23 MOL 1 14.040 17.798 -0.803 1.00 0.00 <br />
ATOM 24 C24 MOL 1 22.410 16.944 -0.094 1.00 0.00 <br />
ATOM 25 H25 MOL 1 19.357 15.031 -1.060 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:49:10 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 17.558 13.998 -0.496 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.076 15.115 0.248 1.00 0.00 <br />
ATOM 3 C3 MOL 1 17.258 16.394 -0.557 1.00 0.00 <br />
ATOM 4 C4 MOL 1 15.561 15.011 0.531 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.860 15.228 1.589 1.00 0.00 <br />
ATOM 6 C6 MOL 1 16.778 17.574 0.073 1.00 0.00 <br />
ATOM 7 C7 MOL 1 18.653 16.799 -0.879 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.508 16.294 -1.921 1.00 0.00 <br />
ATOM 9 C9 MOL 1 15.127 16.315 1.434 1.00 0.00 <br />
ATOM 10 N10 MOL 1 14.843 14.899 -0.812 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.354 15.543 1.336 1.00 0.00 <br />
ATOM 12 C12 MOL 1 17.493 18.660 -0.426 1.00 0.00 <br />
ATOM 13 C13 MOL 1 15.791 17.648 0.954 1.00 0.00 <br />
ATOM 14 O14 MOL 1 18.548 18.231 -1.333 1.00 0.00 <br />
ATOM 15 C15 MOL 1 19.467 16.754 0.400 1.00 0.00 <br />
ATOM 16 C16 MOL 1 15.014 16.064 -1.686 1.00 0.00 <br />
ATOM 17 C17 MOL 1 13.406 14.609 -0.651 1.00 0.00 <br />
ATOM 18 C18 MOL 1 17.129 19.900 -0.114 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.387 18.995 1.400 1.00 0.00 <br />
ATOM 20 O20 MOL 1 20.317 17.624 0.613 1.00 0.00 <br />
ATOM 21 C21 MOL 1 13.178 13.073 -0.836 1.00 0.00 <br />
ATOM 22 O22 MOL 1 17.801 20.995 -0.638 1.00 0.00 <br />
ATOM 23 C23 MOL 1 16.014 20.069 0.881 1.00 0.00 <br />
ATOM 24 C24 MOL 1 11.870 12.702 -0.129 1.00 0.00 <br />
ATOM 25 C25 MOL 1 13.234 12.318 0.500 1.00 0.00 <br />
ATOM 26 H26 MOL 1 19.132 16.101 -1.579 1.00 0.00 <br />
ATOM 27 H27 MOL 1 15.339 14.101 1.101 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Naloxone<br />
|Naltrexone<br />
|-<br />
|}<br />
<br />
<br />
<br />
Both naloxone and naltrexone are competitive antagonists at the μ- and κ-opioid receptors, and to a lesser extent at δ-opioid receptors. The blockade of these receptors is what prevents the opiods such as morphine, from combining with these receptor sites thus preventing the side effects usually caused by morphine.<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroine<br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br><br />
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br><br />
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.<br />
<br />
<br><br />
<br />
<br />
==Synthesis of Codeine from Morphine==<br />
[[Image:codeine_s.gif|thumb|Synthesis of Codeine]]<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]<br />
*Schmitz J, Stotts A, Rhoades H, Grabowski J. "Naltrexone and relapse prevention treatment for cocaine-dependent patients.". Addict Behav 26 (2): 167-80. PMID 11316375. <br />
*Chicago Recovery Alliance's naloxone distrobution project<br />
*Synthesis of codeine from morphine. Ai, Lin; Chen, Xiaoyuan; Zhang, Le. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005)</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=4194
It:Morphine
2006-10-26T13:06:45Z
<p>Ffs05: changed formating of 3D strucutures</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
== Properties of Morphine ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data''' <br />
|-<br />
| IUPAC Name<br />
| align="center"|7,8-didehydro-<br />
4,5-epoxy-17-methylmorphinan-3,6-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub><br />
|-<br />
| Molar Mass<br />
| align="center"|285.4 g/mol<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''<br />
|-<br />
| Bioavailability<br />
| align="center"|... ~30%<br />
|-<br />
| Protein binding<br />
| align="center"|... 30–40%<br />
|-<br />
| Metabolism<br />
| align="center"|... Hepatic 90%<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''<br />
|-<br />
| Pregnancy cat.<br />
| align="center"| C(AU) C(US)<br />
|-<br />
| Legal status<br />
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only<br />
|-<br />
| Dependence Liability<br />
| align="center"| Extremely High<br />
|-<br />
| Routes<br />
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
<br />
<br />
==Pharmacology of Morphine==<br />
<br />
Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|<br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:48:06 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 18.255 13.156 0.573 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.569 14.167 -0.163 1.00 0.00 <br />
ATOM 3 C3 MOL 1 16.417 14.732 0.663 1.00 0.00 <br />
ATOM 4 C4 MOL 1 18.496 15.366 -0.471 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.015 13.567 -1.482 1.00 0.00 <br />
ATOM 6 C6 MOL 1 15.693 15.779 0.018 1.00 0.00 <br />
ATOM 7 C7 MOL 1 15.307 13.777 1.020 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.942 15.313 2.010 1.00 0.00 <br />
ATOM 9 C9 MOL 1 17.646 16.451 -1.361 1.00 0.00 <br />
ATOM 10 N10 MOL 1 19.019 15.899 0.861 1.00 0.00 <br />
ATOM 11 C11 MOL 1 15.959 12.473 -1.196 1.00 0.00 <br />
ATOM 12 C12 MOL 1 14.403 15.799 0.518 1.00 0.00 <br />
ATOM 13 C13 MOL 1 16.179 16.645 -0.862 1.00 0.00 <br />
ATOM 14 O14 MOL 1 14.159 14.689 1.403 1.00 0.00 <br />
ATOM 15 C15 MOL 1 14.899 12.986 -0.210 1.00 0.00 <br />
ATOM 16 C16 MOL 1 17.969 16.420 1.747 1.00 0.00 <br />
ATOM 17 C17 MOL 1 20.056 16.927 0.663 1.00 0.00 <br />
ATOM 18 C18 MOL 1 13.566 16.775 0.184 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.281 17.721 -1.321 1.00 0.00 <br />
ATOM 20 O20 MOL 1 13.720 12.646 -0.346 1.00 0.00 <br />
ATOM 21 C21 MOL 1 21.259 16.286 0.008 1.00 0.00 <br />
ATOM 22 O22 MOL 1 12.278 16.816 0.702 1.00 0.00 <br />
ATOM 23 C23 MOL 1 14.040 17.798 -0.803 1.00 0.00 <br />
ATOM 24 C24 MOL 1 22.410 16.944 -0.094 1.00 0.00 <br />
ATOM 25 H25 MOL 1 19.357 15.031 -1.060 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Thu Oct 26 11:49:10 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 17.558 13.998 -0.496 1.00 0.00 <br />
ATOM 2 C2 MOL 1 17.076 15.115 0.248 1.00 0.00 <br />
ATOM 3 C3 MOL 1 17.258 16.394 -0.557 1.00 0.00 <br />
ATOM 4 C4 MOL 1 15.561 15.011 0.531 1.00 0.00 <br />
ATOM 5 C5 MOL 1 17.860 15.228 1.589 1.00 0.00 <br />
ATOM 6 C6 MOL 1 16.778 17.574 0.073 1.00 0.00 <br />
ATOM 7 C7 MOL 1 18.653 16.799 -0.879 1.00 0.00 <br />
ATOM 8 C8 MOL 1 16.508 16.294 -1.921 1.00 0.00 <br />
ATOM 9 C9 MOL 1 15.127 16.315 1.434 1.00 0.00 <br />
ATOM 10 N10 MOL 1 14.843 14.899 -0.812 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.354 15.543 1.336 1.00 0.00 <br />
ATOM 12 C12 MOL 1 17.493 18.660 -0.426 1.00 0.00 <br />
ATOM 13 C13 MOL 1 15.791 17.648 0.954 1.00 0.00 <br />
ATOM 14 O14 MOL 1 18.548 18.231 -1.333 1.00 0.00 <br />
ATOM 15 C15 MOL 1 19.467 16.754 0.400 1.00 0.00 <br />
ATOM 16 C16 MOL 1 15.014 16.064 -1.686 1.00 0.00 <br />
ATOM 17 C17 MOL 1 13.406 14.609 -0.651 1.00 0.00 <br />
ATOM 18 C18 MOL 1 17.129 19.900 -0.114 1.00 0.00 <br />
ATOM 19 C19 MOL 1 15.387 18.995 1.400 1.00 0.00 <br />
ATOM 20 O20 MOL 1 20.317 17.624 0.613 1.00 0.00 <br />
ATOM 21 C21 MOL 1 13.178 13.073 -0.836 1.00 0.00 <br />
ATOM 22 O22 MOL 1 17.801 20.995 -0.638 1.00 0.00 <br />
ATOM 23 C23 MOL 1 16.014 20.069 0.881 1.00 0.00 <br />
ATOM 24 C24 MOL 1 11.870 12.702 -0.129 1.00 0.00 <br />
ATOM 25 C25 MOL 1 13.234 12.318 0.500 1.00 0.00 <br />
ATOM 26 H26 MOL 1 19.132 16.101 -1.579 1.00 0.00 <br />
ATOM 27 H27 MOL 1 15.339 14.101 1.101 1.00 0.00 <br />
TER</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Naloxone<br />
|Naltrexone<br />
|-<br />
|}<br />
<br />
<br />
<br />
Both naloxone and naltrexone are competitive antagonists at the μ- and κ-opioid receptors, and to a lesser extent at δ-opioid receptors. The blockade of these receptors is what prevents the opiods such as morphine, from combining with these receptor sites thus preventing the side effects usually caused by morphine.<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroine<br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br><br />
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br><br />
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.<br />
<br />
<br><br />
<br />
<br />
==Synthesis of Codeine from Morphine==<br />
[[Image:codeine_s.gif|thumb|Synthesis of Codeine]]<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]<br />
*Schmitz J, Stotts A, Rhoades H, Grabowski J. "Naltrexone and relapse prevention treatment for cocaine-dependent patients.". Addict Behav 26 (2): 167-80. PMID 11316375. <br />
*Chicago Recovery Alliance's naloxone distrobution project</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=4138
It:Morphine
2006-10-26T10:59:06Z
<p>Ffs05: added synthesis of codeine</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
== Properties of Morphine ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data''' <br />
|-<br />
| Chemical name<br />
| align="center"|7,8-didehydro-<br />
4,5-epoxy-17-methylmorphinan-3,6-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub><br />
|-<br />
| Molar Mass<br />
| align="center"|285.4 g/mol<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''<br />
|-<br />
| Bioavailability<br />
| align="center"|... ~30%<br />
|-<br />
| Protein binding<br />
| align="center"|... 30–40%<br />
|-<br />
| Metabolism<br />
| align="center"|... Hepatic 90%<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''<br />
|-<br />
| Pregnancy cat.<br />
| align="center"| C(AU) C(US)<br />
|-<br />
| Legal status<br />
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only<br />
|-<br />
| Dependence Liability<br />
| align="center"| Extremely High<br />
|-<br />
| Routes<br />
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
<br />
<br />
==Pharmacology of Morphine==<br />
<br />
Morphine is an opiod receptor agaonist whose main function is to bind and activate the µ-opioid receptors in the central nervous system.The activation of these receptors is what leads to euphoria, sedation, analgesia, physical dependence and respiratory depression. Morphine is also a κ-opioid receptor agonist, which is associated with spinal analgesia and miosis. These effects of Morphine can only be countered with naloxone or naltrexone.<br />
<br />
<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroine<br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br><br />
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br><br />
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.<br />
<br />
<br><br />
Click on the thumbnail to view the enlarged synthesis of codeine from morphine.<br />
[[Image:codeine_s.gif|thumb|Synthesis of Codeine]]<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Codeine_s.gif&diff=4130
File:Codeine s.gif
2006-10-26T10:54:47Z
<p>Ffs05: </p>
<hr />
<div></div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=4101
It:Morphine
2006-10-26T10:33:00Z
<p>Ffs05: /* Properties of Morphine */</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
== Properties of Morphine ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data''' <br />
|-<br />
| Chemical name<br />
| align="center"|7,8-didehydro-<br />
4,5-epoxy-17-methylmorphinan-3,6-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>17</sub>H<sub>19</sub>NO<sub>3</sub><br />
|-<br />
| Molar Mass<br />
| align="center"|285.4 g/mol<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''<br />
|-<br />
| Bioavailability<br />
| align="center"|... ~30%<br />
|-<br />
| Protein binding<br />
| align="center"|... 30–40%<br />
|-<br />
| Metabolism<br />
| align="center"|... Hepatic 90%<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''<br />
|-<br />
| Pregnancy cat.<br />
| align="center"| C(AU) C(US)<br />
|-<br />
| Legal status<br />
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only<br />
|-<br />
| Dependence Liability<br />
| align="center"| Extremely High<br />
|-<br />
| Routes<br />
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroine<br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br><br />
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br><br />
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.<br />
<br />
<br><br />
Click here to view the synthesis of codeine from morphine.<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=4093
It:Morphine
2006-10-26T10:19:41Z
<p>Ffs05: corrected molecular formula</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
== Properties of Morphine ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data''' <br />
|-<br />
| Chemical name<br />
| align="center"|7,8-didehydro-<br />
4,5-epoxy-17-methylmorphinan-3,6-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>16</sub>H<sub>17</sub>NO<sub>3</sub><br />
|-<br />
| Molar Mass<br />
| align="center"|285.4 g/mol<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''<br />
|-<br />
| Bioavailability<br />
| align="center"|... ~30%<br />
|-<br />
| Protein binding<br />
| align="center"|... 30–40%<br />
|-<br />
| Metabolism<br />
| align="center"|... Hepatic 90%<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''<br />
|-<br />
| Pregnancy cat.<br />
| align="center"| C(AU) C(US)<br />
|-<br />
| Legal status<br />
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only<br />
|-<br />
| Dependence Liability<br />
| align="center"| Extremely High<br />
|-<br />
| Routes<br />
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroine<br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br><br />
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br><br />
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.<br />
<br />
<br><br />
Click here to view the synthesis of codeine from morphine.<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=4091
It:Morphine
2006-10-26T10:16:46Z
<p>Ffs05: /* Derrivatives of Morphine */</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
== Properties of Morphine ==<br />
<br />
{| class="toccolours" border="1" style="fix : right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Chemical Data''' <br />
|-<br />
| Chemical name<br />
| align="center"|7,8-didehydro-<br />
4,5-epoxy-17-methylmorphinan-3,6-diol<br />
|-<br />
| Chemical formula<br />
| align="center"|C<sub>20</sub>H<sub>28</sub>O<br />
|-<br />
| Molar Mass<br />
| align="center"|285.4 g/mol<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Pharmakenetic Data'''<br />
|-<br />
| Bioavailability<br />
| align="center"|... ~30%<br />
|-<br />
| Protein binding<br />
| align="center"|... 30–40%<br />
|-<br />
| Metabolism<br />
| align="center"|... Hepatic 90%<br />
|-<br />
| align="center" colspan="2" bgcolor="lt blue" |'''Therapeutic Considerations'''<br />
|-<br />
| Pregnancy cat.<br />
| align="center"| C(AU) C(US)<br />
|-<br />
| Legal status<br />
| align="center"|S8(AU) Schedule I(CA) Class A(UK) Schedule II(US) Prescription only<br />
|-<br />
| Dependence Liability<br />
| align="center"| Extremely High<br />
|-<br />
| Routes<br />
| align="center"| smoked/inhaled, insufflated, Oral, SC, IM, IV<br />
|-<br />
|}<br />
<br />
<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroine<br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, it becomes clear that there are only slight differences. If one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br><br />
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br><br />
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.<br />
<br />
<br><br />
Click here to view the synthesis of codeine from morphine.<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=3923
It:Morphine
2006-10-24T15:20:14Z
<p>Ffs05: more text added to derrivatives</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroine<br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, i becomes clear that there are only slight differences. Then one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br><br />
Codeine is used as an analgesic, in a similar way to morphine. It is not as effective as morphine, however the addiction potential is much lower than that of morphine.<br><br />
Heroin acts as a very strong analgesic with an extremely strong potential for addiciotn. For obvoius reasons the synthesis of heroin will be omited.<br />
<br />
<br><br />
Click here to view the synthesis of codeine from morphine.<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=3911
It:Morphine
2006-10-24T14:59:49Z
<p>Ffs05: /* Derrivatives of Morphine */</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroine<br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, i becomes clear that there are only slight differences. Then one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br />
<br />
Click here to view the sunthesis of codeine from morphine.<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=3905
It:Morphine
2006-10-24T14:53:33Z
<p>Ffs05: added more text to derrivatives section</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroine<br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Morphine with those of Codeine and Heroine, i becomes clear that there are only slight differences. Then one of the OH groups from Morphine (marked in red) is replaced by a OMe group it becomes codeine. If these -OH groups are both replaced bu CH<sub>3</sub>COO group it becomes heroin.<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=3892
It:Morphine
2006-10-24T14:30:44Z
<p>Ffs05: added 2D structures in derrivatives section</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.gif]]<br />
|[[Image:codeine.gif]]<br />
|[[Image:heroin.gif]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroine<br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Codeine and Heroin with that of Morphine it is clearly visible that a slight change in the structure leads to the fomration of completely different molecules.<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Heroin.gif&diff=3889
File:Heroin.gif
2006-10-24T14:29:39Z
<p>Ffs05: </p>
<hr />
<div></div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Morphine.gif&diff=3887
File:Morphine.gif
2006-10-24T14:27:51Z
<p>Ffs05: </p>
<hr />
<div></div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Codeine.gif&diff=3886
File:Codeine.gif
2006-10-24T14:27:44Z
<p>Ffs05: </p>
<hr />
<div></div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Cocaine.gif&diff=3884
File:Cocaine.gif
2006-10-24T14:27:36Z
<p>Ffs05: </p>
<hr />
<div></div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=3881
It:Morphine
2006-10-24T14:13:03Z
<p>Ffs05: added text to derrivatives section</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
Morphine can be used to synthesize a variety of different opiates. Some of the most prominent examples include:<br />
<br><br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|[[Image:morphine.GIF]]<br />
|[[Image:codeine.GIF]]<br />
|[[Image:heroine.GIF]]<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|Morphine<br />
|Codeine<br />
|Heroine<br />
|-<br />
|}<br />
<br><br />
When comparing the structures of Codeine and Heroin with that of Morphine it is clearly visible that a slight change in the structure leads to the fomration of completely different molecules.<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=3824
It:Morphine
2006-10-24T13:09:27Z
<p>Ffs05: added reference</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month<br />
*[http://holivo.pharmacy.uiowa.edu/morphine/morphine.html Opioid Analgesics]</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=3815
It:Morphine
2006-10-24T13:06:04Z
<p>Ffs05: /* 3D Structure of Morphine */</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=3814
It:Morphine
2006-10-24T13:05:52Z
<p>Ffs05: Rearrangement of structural pictures</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==3D Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=3810
It:Morphine
2006-10-24T13:05:06Z
<p>Ffs05: /* 3D Structure of Morphine */</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==3D Structure of Morphine==<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
|<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
|-<br />
|}<br />
<br />
==2D Structure of Morphine==<br />
<br />
<br />
[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
<br />
<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=3799
It:Morphine
2006-10-24T12:59:11Z
<p>Ffs05: formated picture of poppy</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy2.GIF]]<br />
|-<br />
|}<br />
<br />
==3D Structure of Morphine==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==2D Structure of Morphine==<br />
<br />
<br />
[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
<br />
<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Poppy2.GIF&diff=3796
File:Poppy2.GIF
2006-10-24T12:53:35Z
<p>Ffs05: </p>
<hr />
<div></div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=3791
It:Morphine
2006-10-24T12:51:56Z
<p>Ffs05: added some text and poppy plant picture</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
<br />
{| class="toccolours" border="0" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|Morphine originates from the dried seeds of the poppy (Papaver somniferum.)Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects such as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
|colspan="5"|[[Image:poppy.GIF]]<br />
|-<br />
|}<br />
<br />
==3D Structure of Morphine==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==2D Structure of Morphine==<br />
<br />
<br />
[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
<br />
<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Poppy.GIF&diff=3763
File:Poppy.GIF
2006-10-24T12:29:45Z
<p>Ffs05: </p>
<hr />
<div></div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Morphine&diff=3758
It:Morphine
2006-10-24T12:23:03Z
<p>Ffs05: added derrivatives section</p>
<hr />
<div>==Introduction to Morphine==<br />
<br />
Morphine is an extremely powerful analgesic drug, whcih is the principal active agent in opium. Morphine acts directly on the central nervous system to reduce pain. It has numerous side effects suc as; impairment of mental performance, euphoria, drowsiness, lethargy and blurred vision. It also causes a decrease in hunger and promotes constipation. Morphine is highly addictive when compared to other substances.<br />
<br />
<br />
==3D Structure of Morphine==<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>300</size><br />
<color>white</color><br />
<script>zoom 100; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 16:25:25 GMT Standard Time 2006<br />
ATOM 1 O1 MOL A 1 17.271 10.541 -0.367 1.00 0.00 <br />
ATOM 2 C2 MOL A 1 17.053 11.947 -0.307 1.00 0.00 <br />
ATOM 3 C3 MOL A 1 16.079 12.347 0.885 1.00 0.00 <br />
ATOM 4 C4 MOL A 1 16.849 12.596 -1.622 1.00 0.00 <br />
ATOM 5 C5 MOL A 1 15.738 13.843 0.665 1.00 0.00 <br />
ATOM 6 O6 MOL A 1 14.699 11.697 0.968 1.00 0.00 <br />
ATOM 7 C7 MOL A 1 16.829 13.949 -1.558 1.00 0.00 <br />
ATOM 8 C8 MOL A 1 14.461 13.758 -0.066 1.00 0.00 <br />
ATOM 9 C9 MOL A 1 16.718 14.681 -0.139 1.00 0.00 <br />
ATOM 10 C10 MOL A 1 15.425 14.437 2.067 1.00 0.00 <br />
ATOM 11 C11 MOL A 1 13.864 12.546 0.196 1.00 0.00 <br />
ATOM 12 C12 MOL A 1 13.912 14.693 -0.837 1.00 0.00 <br />
ATOM 13 C13 MOL A 1 16.073 16.095 -0.291 1.00 0.00 <br />
ATOM 14 C14 MOL A 1 14.917 15.878 1.928 1.00 0.00 <br />
ATOM 15 C15 MOL A 1 12.642 12.273 -0.245 1.00 0.00 <br />
ATOM 16 C16 MOL A 1 14.719 15.958 -1.155 1.00 0.00 <br />
ATOM 17 C17 MOL A 1 12.576 14.438 -1.393 1.00 0.00 <br />
ATOM 18 N18 MOL A 1 15.850 16.672 1.091 1.00 0.00 <br />
ATOM 19 O19 MOL A 1 12.041 11.056 0.042 1.00 0.00 <br />
ATOM 20 C20 MOL A 1 11.954 13.288 -1.088 1.00 0.00 <br />
ATOM 21 C21 MOL A 1 15.314 18.035 0.964 1.00 0.00 <br />
ATOM 22 H22 MOL A 1 17.683 14.729 0.384 1.00 0.00 <br />
ATOM 23 H23 MOL A 1 16.722 12.088 1.736 1.00 0.00 <br />
ATOM 24 H24 MOL A 1 16.744 16.773 -0.837 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==2D Structure of Morphine==<br />
<br />
<br />
[[Image:200px-Morphine-2D-skeletal.GIF]]<br />
<br />
<br />
<br />
==Uses==<br />
<br />
Morphine is used legally:<br />
<br />
*analgesic in hospital settings for <br />
*Pain after surgery <br />
*Pain associated with trauma <br />
*In the relief of severe chronic pain <br />
*Cancer pain <br />
*Pain from kidney stones <br />
*Back pain <br />
*In epidural anesthesia <br />
*As an antitussive for severe cough <br />
*As an antidiarrheal in chronic conditions (e.g., for diarrhea associated with AIDS) <br />
*To relieve breathlessness in patients in respiratory failure<br />
<br />
==Derrivatives of Morphine==<br />
<br />
==References and External Links==<br />
*Morphine Apparently in Your Head -- Wired Magazine article about endogenous production of morphine <br />
*Morphine, Molecule of the Month</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3542
It:Gentamycin
2006-10-23T15:35:39Z
<p>Ffs05: spelling correction</p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
====Side Effects====<br />
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).<br />
<br />
In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:<br />
*deafness<br />
*loss of equilibrium<br />
<br />
The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00 <br />
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00 <br />
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00 <br />
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00 <br />
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00 <br />
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00 <br />
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00 <br />
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00 <br />
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00 <br />
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00 <br />
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00 <br />
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
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-3.4860 2.9650 0.3570 O 0 0 0 0 0 0 0 0 0 5<br />
-3.6860 1.6300 -1.6520 C 0 0 1 0 0 0 0 0 0 6<br />
-3.5880 2.8380 -2.4090 O 0 0 0 0 0 0 0 0 0 7<br />
-2.2910 1.0170 -1.4800 C 0 0 1 0 0 0 0 0 0 8<br />
-1.3800 2.0190 -0.9120 N 0 0 0 0 0 0 0 0 0 9<br />
-2.3880 -0.1830 -0.5340 C 0 0 1 0 0 0 0 0 0 10<br />
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-2.8540 0.2460 0.7440 O 0 0 0 0 0 0 0 0 0 32<br />
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-4.1900 1.6840 2.4900 H 0 0 0 0 0 0 0 0 0 35<br />
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1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54<br />
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55<br />
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6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60<br />
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6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62<br />
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0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68<br />
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30 67 1 0 0 0<br />
M END<br />
<br />
<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
== Properties of Gentamycin ==<br />
<br />
'''Physical propertites'''<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General'''<br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| solubility in water<br />
| align="center"| 100mg/mL<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| CA Index Name<br />
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
|-<br />
|CAS Registry Number<br />
| align="center"| 13291-74-2<br />
|-<br />
|}<br />
'''Pharmacokinetic properties'''<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General''' <br />
|-<br />
| Toxicity<br />
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.<br />
|- <br />
| Protein bonding<br />
| align="left"|Low (between 0 and 30%)<br />
|-<br />
| Half life<br />
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.<br />
|-<br />
| Dosage form<br />
| align="left"|Cream Drops Liquid Ointment Solution <br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
*Sci Finder, Registry Number: 13291-74-2<br />
*http://en.wikipedia.org/wiki/Gentamicin</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3541
It:Gentamycin
2006-10-23T15:34:19Z
<p>Ffs05: added reference</p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
====Side Effects====<br />
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).<br />
<br />
In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:<br />
*deafness<br />
*loss of equilibrium<br />
<br />
The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
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ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
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<br />
== Properties of Gentacymin ==<br />
<br />
'''Physical propertites'''<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General'''<br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| solubility in water<br />
| align="center"| 100mg/mL<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| CA Index Name<br />
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
|-<br />
|CAS Registry Number<br />
| align="center"| 13291-74-2<br />
|-<br />
|}<br />
'''Pharmacokinetic properties'''<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General''' <br />
|-<br />
| Toxicity<br />
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.<br />
|- <br />
| Protein bonding<br />
| align="left"|Low (between 0 and 30%)<br />
|-<br />
| Half life<br />
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.<br />
|-<br />
| Dosage form<br />
| align="left"|Cream Drops Liquid Ointment Solution <br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
*Sci Finder, Registry Number: 13291-74-2<br />
*http://en.wikipedia.org/wiki/Gentamicin</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3539
It:Gentamycin
2006-10-23T15:33:24Z
<p>Ffs05: /* Properties of Gentacymin */</p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
====Side Effects====<br />
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).<br />
<br />
In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:<br />
*deafness<br />
*loss of equilibrium<br />
<br />
The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
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<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
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TER<br />
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M END<br />
<br />
<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
== Properties of Gentacymin ==<br />
<br />
'''Physical propertites'''<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General'''<br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| solubility in water<br />
| align="center"| 100mg/mL<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| CA Index Name<br />
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
|-<br />
|CAS Registry Number<br />
| align="center"| 13291-74-2<br />
|-<br />
|}<br />
'''Pharmacokinetic properties'''<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General''' <br />
|-<br />
| Toxicity<br />
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.<br />
|- <br />
| Protein bonding<br />
| align="left"|Low (between 0 and 30%)<br />
|-<br />
| Half life<br />
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.<br />
|-<br />
| Dosage form<br />
| align="left"|Cream Drops Liquid Ointment Solution <br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
Sci Finder, Registry Number: 13291-74-2</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3538
It:Gentamycin
2006-10-23T15:32:38Z
<p>Ffs05: added side effects part</p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
====Side Effects====<br />
Gentamycin can cause kidney damage in high dosages (especially in individuals with existing renal conditions).<br />
<br />
In individuals with a certain DNA mutation that allows the gentamacyn to attack their cells side effects can include:<br />
*deafness<br />
*loss of equilibrium<br />
<br />
The reason for this is that the cells around the ears are especially volunerable for the attack of the gentamycin.<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00 <br />
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00 <br />
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00 <br />
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00 <br />
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00 <br />
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00 <br />
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00 <br />
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00 <br />
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00 <br />
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00 <br />
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00 <br />
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
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1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57<br />
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6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60<br />
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6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62<br />
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63<br />
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64<br />
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M END<br />
<br />
<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
== Properties of Gentacymin ==<br />
<br />
'''Physical propertites'''<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''Physical Properties'''<br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| solubility in water<br />
| align="center"| 100mg/mL<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| CA Index Name<br />
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
|-<br />
|CAS Registry Number<br />
| align="center"| 13291-74-2<br />
|-<br />
|}<br />
'''Pharmacokinetic properties'''<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General''' <br />
|-<br />
| Toxicity<br />
| align="left"|Mouse, Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.<br />
|- <br />
| Protein bonding<br />
| align="left"|Low (between 0 and 30%)<br />
|-<br />
| Half life<br />
| align="left"|3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.<br />
|-<br />
| Dosage form<br />
| align="left"|Cream Drops Liquid Ointment Solution <br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
Sci Finder, Registry Number: 13291-74-2</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3480
It:Gentamycin
2006-10-23T15:10:53Z
<p>Ffs05: changed properties section formating</p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00 <br />
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00 <br />
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00 <br />
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00 <br />
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00 <br />
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00 <br />
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00 <br />
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00 <br />
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00 <br />
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00 <br />
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00 <br />
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
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M END<br />
<br />
<br />
<br />
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</jmol><br />
<br />
== Properties of Gentacymin ==<br />
<br />
<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''Physical Properties'''<br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| solubility in water<br />
| align="center"| 100mg/mL<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| CA Index Name<br />
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
|-<br />
|CAS Registry Number<br />
| align="center"| 13291-74-2<br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
Sci Finder, Registry Number: 13291-74-2</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3473
It:Gentamycin
2006-10-23T15:07:15Z
<p>Ffs05: /* Properties of Gentacymin */</p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
<jmolApplet><br />
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<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00 <br />
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00 <br />
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00 <br />
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00 <br />
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00 <br />
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00 <br />
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00 <br />
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00 <br />
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00 <br />
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00 <br />
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00 <br />
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
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30 67 1 0 0 0<br />
M END<br />
<br />
<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
== Properties of Gentacymin ==<br />
<br />
'''physical properties'''<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General''' <br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| solubility in water<br />
| align="center"| 100mg/mL<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| CA Index Name<br />
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
|-<br />
|CAS Registry Number<br />
| align="center"| 13291-74-2<br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
Sci Finder, Registry Number: 13291-74-2</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3472
It:Gentamycin
2006-10-23T15:06:40Z
<p>Ffs05: /* Properties of Gentacymin */</p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00 <br />
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00 <br />
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00 <br />
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00 <br />
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00 <br />
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00 <br />
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00 <br />
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00 <br />
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00 <br />
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00 <br />
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00 <br />
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
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30 67 1 0 0 0<br />
M END<br />
<br />
<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
== Properties of Gentacymin ==<br />
<br />
'''physical properties'''<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General''' <br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| solubility in water<br />
| align="center"| 100mg/mL<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| CAS Index Name<br />
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
|-<br />
|CAS Registry Number<br />
| align="center"| 13291-74-2<br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
Sci Finder, Registry Number: 13291-74-2</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3418
It:Gentamycin
2006-10-23T14:48:22Z
<p>Ffs05: formated table</p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00 <br />
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00 <br />
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00 <br />
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00 <br />
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00 <br />
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00 <br />
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00 <br />
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00 <br />
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00 <br />
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00 <br />
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00 <br />
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
68 70 0 0 0 0 0 0 0 0999 V2000<br />
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-0.1450 -1.2630 2.2230 O 0 0 0 0 0 0 0 0 0 31<br />
-2.8540 0.2460 0.7440 O 0 0 0 0 0 0 0 0 0 32<br />
-5.2540 -0.0280 3.5810 H 0 0 0 0 0 0 0 0 0 33<br />
-5.8170 1.3580 1.8450 H 0 0 0 0 0 0 0 0 0 34<br />
-4.1900 1.6840 2.4900 H 0 0 0 0 0 0 0 0 0 35<br />
-4.7790 -0.1210 0.1020 H 0 0 0 0 0 0 0 0 0 36<br />
-5.2940 2.2690 -0.3620 H 0 0 0 0 0 0 0 0 0 37<br />
-3.9350 3.1930 1.1830 H 0 0 0 0 0 0 0 0 0 38<br />
-4.3370 0.9260 -2.1690 H 0 0 0 0 0 0 0 0 0 39<br />
-4.4830 3.1960 -2.4810 H 0 0 0 0 0 0 0 0 0 40<br />
-1.9150 0.6890 -2.4490 H 0 0 0 0 0 0 0 0 0 41<br />
-0.4630 1.5980 -0.8890 H 0 0 0 0 0 0 0 0 0 42<br />
-1.3340 2.7780 -1.5750 H 0 0 0 0 0 0 0 0 0 43<br />
-3.0830 -0.9140 -0.9450 H 0 0 0 0 0 0 0 0 0 44<br />
-2.2470 -2.0370 0.7780 H 0 0 0 0 0 0 0 0 0 45<br />
-1.4610 -4.1150 -0.3220 H 0 0 0 0 0 0 0 0 0 46<br />
-2.3720 -3.6580 -2.4340 H 0 0 0 0 0 0 0 0 0 47<br />
-3.2630 -3.0120 -1.2470 H 0 0 0 0 0 0 0 0 0 48<br />
0.0160 -3.9510 -2.3080 H 0 0 0 0 0 0 0 0 0 49<br />
0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50<br />
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51<br />
2.4310 -4.2300 -1.8900 H 0 0 0 0 0 0 0 0 0 52<br />
2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53<br />
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54<br />
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55<br />
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56<br />
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57<br />
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58<br />
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59<br />
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60<br />
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61<br />
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62<br />
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63<br />
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64<br />
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65<br />
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66<br />
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67<br />
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68<br />
1 2 1 0 0 0<br />
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M END<br />
<br />
<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
== Properties of Gentacymin ==<br />
<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General''' <br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| solubility in water<br />
| align="center"| 100mg/mL<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| CA Index Name<br />
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-<br>[3-deoxy-3-(methylamino)-&alpha-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
Sci Finder, Registry Number: 13291-74-2</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3405
It:Gentamycin
2006-10-23T14:44:30Z
<p>Ffs05: moved info to properties</p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00 <br />
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00 <br />
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00 <br />
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00 <br />
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00 <br />
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00 <br />
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00 <br />
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00 <br />
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00 <br />
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00 <br />
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00 <br />
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
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-4.4830 3.1960 -2.4810 H 0 0 0 0 0 0 0 0 0 40<br />
-1.9150 0.6890 -2.4490 H 0 0 0 0 0 0 0 0 0 41<br />
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-3.0830 -0.9140 -0.9450 H 0 0 0 0 0 0 0 0 0 44<br />
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-2.3720 -3.6580 -2.4340 H 0 0 0 0 0 0 0 0 0 47<br />
-3.2630 -3.0120 -1.2470 H 0 0 0 0 0 0 0 0 0 48<br />
0.0160 -3.9510 -2.3080 H 0 0 0 0 0 0 0 0 0 49<br />
0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50<br />
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51<br />
2.4310 -4.2300 -1.8900 H 0 0 0 0 0 0 0 0 0 52<br />
2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53<br />
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54<br />
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55<br />
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56<br />
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57<br />
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58<br />
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59<br />
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60<br />
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61<br />
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62<br />
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63<br />
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64<br />
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65<br />
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66<br />
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67<br />
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68<br />
1 2 1 0 0 0<br />
1 33 1 0 0 0<br />
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17 53 1 0 0 0<br />
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25 61 1 0 0 0<br />
25 62 1 0 0 0<br />
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28 65 1 0 0 0<br />
30 67 1 0 0 0<br />
M END<br />
<br />
<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
== Properties of Gentacymin ==<br />
<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General''' <br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| solubility in water<br />
| align="center"| 100mg/mL<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| CA Index Name<br />
| align="center"|D-Streptamine, O-2-amino-2-deoxy-a-D-glucopyranosyl-(1->4)-O-[3-deoxy-3-(methylamino)-a-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
Sci Finder, Registry Number: 13291-74-2</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3396
It:Gentamycin
2006-10-23T14:38:49Z
<p>Ffs05: moved some info to properties</p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00 <br />
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00 <br />
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00 <br />
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00 <br />
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00 <br />
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00 <br />
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00 <br />
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00 <br />
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00 <br />
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00 <br />
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00 <br />
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
</inlineContents><br />
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M END<br />
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<br />
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</jmol><br />
<br />
== Properties of Gentacymin ==<br />
<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General''' <br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| solubility in water<br />
| align="center"| 100mg/mL<br />
|-<br />
|align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| <br />
| align="center"|...<br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
Sci Finder, Registry Number: 13291-74-2</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3387
It:Gentamycin
2006-10-23T14:35:07Z
<p>Ffs05: </p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
Gentamycin A (also knwon as: Gentamicin A (7CI) or Streptamine) has the chemical formula C18 H36 N4 O10. Its CA-Index name is:<br> O-2-amino-2-deoxy-a-D-glucopyranosyl-(1®4)-O-[3-deoxy-3-(methylamino)-a-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
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<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00 <br />
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00 <br />
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00 <br />
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00 <br />
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00 <br />
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00 <br />
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00 <br />
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00 <br />
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00 <br />
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00 <br />
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00 <br />
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
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27 26 1 0 0 0<br />
27 64 1 0 0 0<br />
29 28 1 0 0 0<br />
29 20 1 0 0 0<br />
31 30 1 0 0 0<br />
31 68 1 0 0 0<br />
32 10 1 0 0 0<br />
32 3 1 0 0 0<br />
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M END<br />
<br />
<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
== Properties of Gentacymin ==<br />
<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General''' <br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| <br />
| align="center"|...<br />
|-<br />
|}<br />
<br />
== References ==<br />
<br />
Sci Finder, Registry Number: 13291-74-2</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3383
It:Gentamycin
2006-10-23T14:34:40Z
<p>Ffs05: /* References */</p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
Gentamycin A (also knwon as: Gentamicin A (7CI) or Streptamine) has the chemical formula C18 H36 N4 O10. Its CA-Index name is:<br> O-2-amino-2-deoxy-a-D-glucopyranosyl-(1®4)-O-[3-deoxy-3-(methylamino)-a-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00 <br />
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00 <br />
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00 <br />
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00 <br />
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00 <br />
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00 <br />
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00 <br />
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00 <br />
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00 <br />
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00 <br />
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00 <br />
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
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-4.2610 1.9380 -0.2640 C 0 0 2 0 0 0 0 0 0 4<br />
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-3.6860 1.6300 -1.6520 C 0 0 1 0 0 0 0 0 0 6<br />
-3.5880 2.8380 -2.4090 O 0 0 0 0 0 0 0 0 0 7<br />
-2.2910 1.0170 -1.4800 C 0 0 1 0 0 0 0 0 0 8<br />
-1.3800 2.0190 -0.9120 N 0 0 0 0 0 0 0 0 0 9<br />
-2.3880 -0.1830 -0.5340 C 0 0 1 0 0 0 0 0 0 10<br />
-1.0970 -0.7810 -0.3920 O 0 0 0 0 0 0 0 0 0 11<br />
-1.2960 -2.0440 0.2460 C 0 0 1 0 0 0 0 0 0 12<br />
-1.3100 -3.1520 -0.8090 C 0 0 1 0 0 0 0 0 0 13<br />
-2.4010 -2.9070 -1.7610 N 0 0 0 0 0 0 0 0 0 14<br />
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1.1770 -2.3080 0.4900 C 0 0 1 0 0 0 0 0 0 18<br />
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4.8480 2.2420 -1.0540 N 0 0 0 0 0 0 0 0 0 24<br />
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4.5570 1.2980 1.1920 C 0 0 2 0 0 0 0 0 0 26<br />
3.7320 2.4240 1.4980 O 0 0 0 0 0 0 0 0 0 27<br />
4.0440 0.0680 1.9440 C 0 0 0 0 0 0 0 0 0 28<br />
2.6910 -0.1930 1.5770 O 0 0 0 0 0 0 0 0 0 29<br />
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-0.1450 -1.2630 2.2230 O 0 0 0 0 0 0 0 0 0 31<br />
-2.8540 0.2460 0.7440 O 0 0 0 0 0 0 0 0 0 32<br />
-5.2540 -0.0280 3.5810 H 0 0 0 0 0 0 0 0 0 33<br />
-5.8170 1.3580 1.8450 H 0 0 0 0 0 0 0 0 0 34<br />
-4.1900 1.6840 2.4900 H 0 0 0 0 0 0 0 0 0 35<br />
-4.7790 -0.1210 0.1020 H 0 0 0 0 0 0 0 0 0 36<br />
-5.2940 2.2690 -0.3620 H 0 0 0 0 0 0 0 0 0 37<br />
-3.9350 3.1930 1.1830 H 0 0 0 0 0 0 0 0 0 38<br />
-4.3370 0.9260 -2.1690 H 0 0 0 0 0 0 0 0 0 39<br />
-4.4830 3.1960 -2.4810 H 0 0 0 0 0 0 0 0 0 40<br />
-1.9150 0.6890 -2.4490 H 0 0 0 0 0 0 0 0 0 41<br />
-0.4630 1.5980 -0.8890 H 0 0 0 0 0 0 0 0 0 42<br />
-1.3340 2.7780 -1.5750 H 0 0 0 0 0 0 0 0 0 43<br />
-3.0830 -0.9140 -0.9450 H 0 0 0 0 0 0 0 0 0 44<br />
-2.2470 -2.0370 0.7780 H 0 0 0 0 0 0 0 0 0 45<br />
-1.4610 -4.1150 -0.3220 H 0 0 0 0 0 0 0 0 0 46<br />
-2.3720 -3.6580 -2.4340 H 0 0 0 0 0 0 0 0 0 47<br />
-3.2630 -3.0120 -1.2470 H 0 0 0 0 0 0 0 0 0 48<br />
0.0160 -3.9510 -2.3080 H 0 0 0 0 0 0 0 0 0 49<br />
0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50<br />
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51<br />
2.4310 -4.2300 -1.8900 H 0 0 0 0 0 0 0 0 0 52<br />
2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53<br />
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54<br />
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55<br />
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56<br />
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57<br />
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58<br />
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59<br />
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60<br />
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61<br />
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62<br />
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63<br />
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64<br />
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65<br />
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66<br />
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67<br />
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68<br />
1 2 1 0 0 0<br />
1 33 1 0 0 0<br />
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30 67 1 0 0 0<br />
M END<br />
<br />
<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
== Properties of Gentacymin ==<br />
<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General''' <br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| <br />
| align="center"|...<br />
|-<br />
|}<br />
<br />
=== References ===<br />
<br />
Sci Finder, Registry Number: 13291-74-2</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3381
It:Gentamycin
2006-10-23T14:33:52Z
<p>Ffs05: </p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
Gentamycin A (also knwon as: Gentamicin A (7CI) or Streptamine) has the chemical formula C18 H36 N4 O10. Its CA-Index name is:<br> O-2-amino-2-deoxy-a-D-glucopyranosyl-(1®4)-O-[3-deoxy-3-(methylamino)-a-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00 <br />
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00 <br />
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00 <br />
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00 <br />
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00 <br />
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00 <br />
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00 <br />
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00 <br />
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00 <br />
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00 <br />
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00 <br />
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
68 70 0 0 0 0 0 0 0 0999 V2000<br />
-4.8690 -0.2540 2.7230 O 0 0 0 0 0 0 0 0 0 1<br />
-4.8110 0.9570 1.9660 C 0 0 0 0 0 0 0 0 0 2<br />
-4.2080 0.6690 0.5900 C 0 0 1 0 0 0 0 0 0 3<br />
-4.2610 1.9380 -0.2640 C 0 0 2 0 0 0 0 0 0 4<br />
-3.4860 2.9650 0.3570 O 0 0 0 0 0 0 0 0 0 5<br />
-3.6860 1.6300 -1.6520 C 0 0 1 0 0 0 0 0 0 6<br />
-3.5880 2.8380 -2.4090 O 0 0 0 0 0 0 0 0 0 7<br />
-2.2910 1.0170 -1.4800 C 0 0 1 0 0 0 0 0 0 8<br />
-1.3800 2.0190 -0.9120 N 0 0 0 0 0 0 0 0 0 9<br />
-2.3880 -0.1830 -0.5340 C 0 0 1 0 0 0 0 0 0 10<br />
-1.0970 -0.7810 -0.3920 O 0 0 0 0 0 0 0 0 0 11<br />
-1.2960 -2.0440 0.2460 C 0 0 1 0 0 0 0 0 0 12<br />
-1.3100 -3.1520 -0.8090 C 0 0 1 0 0 0 0 0 0 13<br />
-2.4010 -2.9070 -1.7610 N 0 0 0 0 0 0 0 0 0 14<br />
0.0260 -3.1610 -1.5560 C 0 0 0 0 0 0 0 0 0 15<br />
1.1630 -3.4160 -0.5650 C 0 0 2 0 0 0 0 0 0 16<br />
2.4450 -3.4250 -1.2820 N 0 0 0 0 0 0 0 0 0 17<br />
1.1770 -2.3080 0.4900 C 0 0 1 0 0 0 0 0 0 18<br />
1.3750 -1.0450 -0.1480 O 0 0 0 0 0 0 0 0 0 19<br />
2.6860 -0.6020 0.2110 C 0 0 1 0 0 0 0 0 0 20<br />
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2.1790 1.6580 -0.4840 O 0 0 0 0 0 0 0 0 0 22<br />
4.5070 1.0190 -0.3140 C 0 0 2 0 0 0 0 0 0 23<br />
4.8480 2.2420 -1.0540 N 0 0 0 0 0 0 0 0 0 24<br />
6.3130 2.2790 -1.1560 C 0 0 0 0 0 0 0 0 0 25<br />
4.5570 1.2980 1.1920 C 0 0 2 0 0 0 0 0 0 26<br />
3.7320 2.4240 1.4980 O 0 0 0 0 0 0 0 0 0 27<br />
4.0440 0.0680 1.9440 C 0 0 0 0 0 0 0 0 0 28<br />
2.6910 -0.1930 1.5770 O 0 0 0 0 0 0 0 0 0 29<br />
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-2.8540 0.2460 0.7440 O 0 0 0 0 0 0 0 0 0 32<br />
-5.2540 -0.0280 3.5810 H 0 0 0 0 0 0 0 0 0 33<br />
-5.8170 1.3580 1.8450 H 0 0 0 0 0 0 0 0 0 34<br />
-4.1900 1.6840 2.4900 H 0 0 0 0 0 0 0 0 0 35<br />
-4.7790 -0.1210 0.1020 H 0 0 0 0 0 0 0 0 0 36<br />
-5.2940 2.2690 -0.3620 H 0 0 0 0 0 0 0 0 0 37<br />
-3.9350 3.1930 1.1830 H 0 0 0 0 0 0 0 0 0 38<br />
-4.3370 0.9260 -2.1690 H 0 0 0 0 0 0 0 0 0 39<br />
-4.4830 3.1960 -2.4810 H 0 0 0 0 0 0 0 0 0 40<br />
-1.9150 0.6890 -2.4490 H 0 0 0 0 0 0 0 0 0 41<br />
-0.4630 1.5980 -0.8890 H 0 0 0 0 0 0 0 0 0 42<br />
-1.3340 2.7780 -1.5750 H 0 0 0 0 0 0 0 0 0 43<br />
-3.0830 -0.9140 -0.9450 H 0 0 0 0 0 0 0 0 0 44<br />
-2.2470 -2.0370 0.7780 H 0 0 0 0 0 0 0 0 0 45<br />
-1.4610 -4.1150 -0.3220 H 0 0 0 0 0 0 0 0 0 46<br />
-2.3720 -3.6580 -2.4340 H 0 0 0 0 0 0 0 0 0 47<br />
-3.2630 -3.0120 -1.2470 H 0 0 0 0 0 0 0 0 0 48<br />
0.0160 -3.9510 -2.3080 H 0 0 0 0 0 0 0 0 0 49<br />
0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50<br />
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51<br />
2.4310 -4.2300 -1.8900 H 0 0 0 0 0 0 0 0 0 52<br />
2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53<br />
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54<br />
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55<br />
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56<br />
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57<br />
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58<br />
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59<br />
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60<br />
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61<br />
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62<br />
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63<br />
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64<br />
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65<br />
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66<br />
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67<br />
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68<br />
1 2 1 0 0 0<br />
1 33 1 0 0 0<br />
5 4 1 0 0 0<br />
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28 66 1 0 0 0<br />
28 65 1 0 0 0<br />
30 67 1 0 0 0<br />
M END<br />
<br />
<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
== Properties of Gentacymin ==<br />
<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General''' <br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| 105°C (218-237°C as sulfate salt) <br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| <br />
| align="center"|...<br />
|-<br />
|}<br />
<br />
=== References ===</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=File:GentamycinA1.gif&diff=3364
File:GentamycinA1.gif
2006-10-23T14:27:41Z
<p>Ffs05: </p>
<hr />
<div></div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=It:Gentamycin&diff=3362
It:Gentamycin
2006-10-23T14:27:20Z
<p>Ffs05: changed 2D picture</p>
<hr />
<div>== Gentamycin A ==<br />
<br />
'''Gentamicin''' (or Gentamycin) is an antibitoic which belongs to the group of antibiotics known as [[Aminoglycosides]]. These types of antibiotics are effective against certain bacterial infections. Gentamicin is effective against Gram negative infections.<br />
<br />
It works by killing the bactreia, through binding at a site on the bacterial ribosome. This causes the production of defective proteins, which are essential for the growth of the bacteria, evntually leading to the bacteria being killed. <br />
<br />
Gentamicin is used to fight many bacterial infections, such as that of the infection of outer ear canal, infections of the eye, infection of the blood etc.<br />
<br />
Like all aminoglycosides, when gentamycin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.<br />
<br />
Gentamycin A (also knwon as: Gentamicin A (7CI) or Streptamine) has the chemical formula C18 H36 N4 O10. Its CA-Index name is:<br> O-2-amino-2-deoxy-a-D-glucopyranosyl-(1®4)-O-[3-deoxy-3-(methylamino)-a-D-xylopyranosyl-(1®6)]-2-deoxy- (9CI)<br />
<br />
== Structure of Gentamycin ==<br />
<br />
[[Image:gentamycinA1.gif]] <br><br />
<jmol><br />
<jmolApplet><br />
<size>250</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>REMARK MSI WebLab Viewer PDB file<br />
REMARK Created: Mon Oct 23 13:01:59 GMT Standard Time 2006<br />
ATOM 1 O1 MOL 1 21.904 14.736 0.272 1.00 0.00 <br />
ATOM 2 C2 MOL 1 20.721 14.058 -0.318 1.00 0.00 <br />
ATOM 3 C3 MOL 1 23.200 14.238 -0.233 1.00 0.00 <br />
ATOM 4 C4 MOL 1 19.398 14.661 0.256 1.00 0.00 <br />
ATOM 5 C5 MOL 1 20.728 12.553 -0.005 1.00 0.00 <br />
ATOM 6 O6 MOL 1 23.450 12.892 0.237 1.00 0.00 <br />
ATOM 7 C7 MOL 1 24.350 15.150 0.266 1.00 0.00 <br />
ATOM 8 O8 MOL 1 19.349 16.063 -0.029 1.00 0.00 <br />
ATOM 9 C9 MOL 1 18.144 13.956 -0.373 1.00 0.00 <br />
ATOM 10 N10 MOL 1 20.690 12.344 1.450 1.00 0.00 <br />
ATOM 11 C11 MOL 1 19.559 11.857 -0.664 1.00 0.00 <br />
ATOM 12 C12 MOL 1 24.663 12.336 -0.280 1.00 0.00 <br />
ATOM 13 N13 MOL 1 24.139 16.521 -0.212 1.00 0.00 <br />
ATOM 14 C14 MOL 1 25.685 14.607 -0.288 1.00 0.00 <br />
ATOM 15 O15 MOL 1 16.925 14.614 0.214 1.00 0.00 <br />
ATOM 16 C16 MOL 1 18.259 12.400 -0.101 1.00 0.00 <br />
ATOM 17 C17 MOL 1 24.766 10.880 0.220 1.00 0.00 <br />
ATOM 18 C18 MOL 1 25.863 13.173 0.212 1.00 0.00 <br />
ATOM 19 O19 MOL 1 26.782 15.419 0.160 1.00 0.00 <br />
ATOM 20 C20 MOL 1 15.612 14.110 -0.196 1.00 0.00 <br />
ATOM 21 N21 MOL 1 17.200 11.639 -0.771 1.00 0.00 <br />
ATOM 22 O22 MOL 1 25.933 10.252 -0.300 1.00 0.00 <br />
ATOM 23 O23 MOL 1 27.086 12.643 -0.299 1.00 0.00 <br />
ATOM 24 C24 MOL 1 14.501 15.079 0.287 1.00 0.00 <br />
ATOM 25 O25 MOL 1 15.373 12.819 0.405 1.00 0.00 <br />
ATOM 26 O26 MOL 1 14.713 16.368 -0.283 1.00 0.00 <br />
ATOM 27 C27 MOL 1 13.124 14.539 -0.166 1.00 0.00 <br />
ATOM 28 C28 MOL 1 14.121 12.246 -0.016 1.00 0.00 <br />
ATOM 29 N29 MOL 1 12.056 15.497 0.281 1.00 0.00 <br />
ATOM 30 C30 MOL 1 12.957 13.117 0.454 1.00 0.00 <br />
ATOM 31 C31 MOL 1 10.716 15.154 -0.232 1.00 0.00 <br />
ATOM 32 O32 MOL 1 11.740 12.482 0.051 1.00 0.00 <br />
TER<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<jmol><br />
<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>Molecule-1<br />
WLViewer 3D 0<br />
<br />
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-4.2610 1.9380 -0.2640 C 0 0 2 0 0 0 0 0 0 4<br />
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-3.5880 2.8380 -2.4090 O 0 0 0 0 0 0 0 0 0 7<br />
-2.2910 1.0170 -1.4800 C 0 0 1 0 0 0 0 0 0 8<br />
-1.3800 2.0190 -0.9120 N 0 0 0 0 0 0 0 0 0 9<br />
-2.3880 -0.1830 -0.5340 C 0 0 1 0 0 0 0 0 0 10<br />
-1.0970 -0.7810 -0.3920 O 0 0 0 0 0 0 0 0 0 11<br />
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1.1630 -3.4160 -0.5650 C 0 0 2 0 0 0 0 0 0 16<br />
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1.1770 -2.3080 0.4900 C 0 0 1 0 0 0 0 0 0 18<br />
1.3750 -1.0450 -0.1480 O 0 0 0 0 0 0 0 0 0 19<br />
2.6860 -0.6020 0.2110 C 0 0 1 0 0 0 0 0 0 20<br />
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2.1790 1.6580 -0.4840 O 0 0 0 0 0 0 0 0 0 22<br />
4.5070 1.0190 -0.3140 C 0 0 2 0 0 0 0 0 0 23<br />
4.8480 2.2420 -1.0540 N 0 0 0 0 0 0 0 0 0 24<br />
6.3130 2.2790 -1.1560 C 0 0 0 0 0 0 0 0 0 25<br />
4.5570 1.2980 1.1920 C 0 0 2 0 0 0 0 0 0 26<br />
3.7320 2.4240 1.4980 O 0 0 0 0 0 0 0 0 0 27<br />
4.0440 0.0680 1.9440 C 0 0 0 0 0 0 0 0 0 28<br />
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-2.8540 0.2460 0.7440 O 0 0 0 0 0 0 0 0 0 32<br />
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-4.1900 1.6840 2.4900 H 0 0 0 0 0 0 0 0 0 35<br />
-4.7790 -0.1210 0.1020 H 0 0 0 0 0 0 0 0 0 36<br />
-5.2940 2.2690 -0.3620 H 0 0 0 0 0 0 0 0 0 37<br />
-3.9350 3.1930 1.1830 H 0 0 0 0 0 0 0 0 0 38<br />
-4.3370 0.9260 -2.1690 H 0 0 0 0 0 0 0 0 0 39<br />
-4.4830 3.1960 -2.4810 H 0 0 0 0 0 0 0 0 0 40<br />
-1.9150 0.6890 -2.4490 H 0 0 0 0 0 0 0 0 0 41<br />
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-1.3340 2.7780 -1.5750 H 0 0 0 0 0 0 0 0 0 43<br />
-3.0830 -0.9140 -0.9450 H 0 0 0 0 0 0 0 0 0 44<br />
-2.2470 -2.0370 0.7780 H 0 0 0 0 0 0 0 0 0 45<br />
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0.0160 -3.9510 -2.3080 H 0 0 0 0 0 0 0 0 0 49<br />
0.1770 -2.1980 -2.0430 H 0 0 0 0 0 0 0 0 0 50<br />
1.0120 -4.3790 -0.0780 H 0 0 0 0 0 0 0 0 0 51<br />
2.4310 -4.2300 -1.8900 H 0 0 0 0 0 0 0 0 0 52<br />
2.4490 -2.6120 -1.8790 H 0 0 0 0 0 0 0 0 0 53<br />
1.9870 -2.4890 1.1970 H 0 0 0 0 0 0 0 0 0 54<br />
3.3940 -1.4190 0.0750 H 0 0 0 0 0 0 0 0 0 55<br />
3.0610 0.2630 -1.7280 H 0 0 0 0 0 0 0 0 0 56<br />
1.2910 1.3140 -0.6520 H 0 0 0 0 0 0 0 0 0 57<br />
5.2150 0.2300 -0.5670 H 0 0 0 0 0 0 0 0 0 58<br />
4.4950 2.1220 -1.9910 H 0 0 0 0 0 0 0 0 0 59<br />
6.6160 3.1740 -1.6990 H 0 0 0 0 0 0 0 0 0 60<br />
6.7460 2.2970 -0.1560 H 0 0 0 0 0 0 0 0 0 61<br />
6.6630 1.3940 -1.6870 H 0 0 0 0 0 0 0 0 0 62<br />
5.5850 1.5070 1.4900 H 0 0 0 0 0 0 0 0 0 63<br />
3.8600 2.6170 2.4370 H 0 0 0 0 0 0 0 0 0 64<br />
4.6610 -0.7950 1.6920 H 0 0 0 0 0 0 0 0 0 65<br />
4.1000 0.2500 3.0170 H 0 0 0 0 0 0 0 0 0 66<br />
-0.3090 -3.2610 1.7240 H 0 0 0 0 0 0 0 0 0 67<br />
0.6220 -1.4260 2.7890 H 0 0 0 0 0 0 0 0 0 68<br />
1 2 1 0 0 0<br />
1 33 1 0 0 0<br />
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5 38 1 0 0 0<br />
7 6 1 0 0 0<br />
7 40 1 0 0 0<br />
9 8 1 0 0 0<br />
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11 10 1 0 0 0<br />
11 12 1 0 0 0<br />
14 13 1 0 0 0<br />
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14 48 1 0 0 0<br />
17 16 1 0 0 0<br />
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17 53 1 0 0 0<br />
19 18 1 0 0 0<br />
19 20 1 0 0 0<br />
22 21 1 0 0 0<br />
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24 23 1 0 0 0<br />
24 25 1 0 0 0<br />
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6 8 1 0 0 0<br />
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12 13 1 0 0 0<br />
13 15 1 0 0 0<br />
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15 16 1 0 0 0<br />
15 50 1 0 0 0<br />
15 49 1 0 0 0<br />
16 51 1 0 0 0<br />
16 18 1 0 0 0<br />
18 30 1 0 0 0<br />
18 54 1 0 0 0<br />
20 55 1 0 0 0<br />
20 21 1 0 0 0<br />
21 56 1 0 0 0<br />
21 23 1 0 0 0<br />
23 58 1 0 0 0<br />
23 26 1 0 0 0<br />
25 60 1 0 0 0<br />
25 61 1 0 0 0<br />
25 62 1 0 0 0<br />
26 63 1 0 0 0<br />
26 28 1 0 0 0<br />
28 66 1 0 0 0<br />
28 65 1 0 0 0<br />
30 67 1 0 0 0<br />
M END<br />
<br />
<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
== Properties of Gentacymin ==<br />
<br />
<br />
{| class="toccolours" border="1" style="fix: right; clear: left; margin: 0 0 1em 1em; border-collapse: collapse;"<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''General''' <br />
|-<br />
| Impirical Forumla<br />
| align="center"|C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub><br />
|-<br />
| Molecular Weight<br />
| align="center"|468.50g/mol<br />
|-<br />
| Molecular Volume<br />
| align="center"| 303.7±5.0 cm<sup>3</sup>mol<sup>-1</sup>(Temp: 20 °CPress: 760 Torr) <br />
|-<br />
| Melting point<br />
| align="center"| °C<br />
|-<br />
| Boiling point<br />
| align="center"| °C<br />
|-<br />
| align="left" colspan="3" bgcolor="white"|'''Other''' <br />
|-<br />
| Smiles String<br />
| align="center"|OCC1C(O)C(O)C(N)C(OC2C(N)CC(N)C(OC3C(O)C(NC)C(O)CO3)C2O)O1 <br />
|-<br />
| <br />
| align="center"|...<br />
|-<br />
|}</div>
Ffs05
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Gentamycina1.gif&diff=3358
File:Gentamycina1.gif
2006-10-23T14:26:42Z
<p>Ffs05: </p>
<hr />
<div></div>
Ffs05