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<p><strong>Cantharidin</strong>, a type of terpenoid, is a poisonous chemical compound secreted by many species of blister beetle, and most notably by the Spanish fly, <em>Lytta vesicatoria</em>. The false blister beetles and cardinal beetles also have cantharidin.</p>
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<h2><span class="mw-headline">History</span></h2>
<div class="thumb tleft">
<div style="WIDTH: 152px" class="thumbinner"><img class="thumbimage" border="0" alt="" src="http://upload.wikimedia.org/wikipedia/commons/thumb/2/22/Black_blister_beetle.jpg/150px-Black_blister_beetle.jpg" width="150" height="137" />
<div class="thumbcaption">
<div class="magnify"><img alt="" src="/skins-1.5/common/images/magnify-clip.png" width="15" height="11" /></div>
Black Blister Beetle <em>Epicauta pennsylvanica</em></div>
</div>
</div>
<p>Cantharidin was first isolated by Pierre Robiquet in 1810. It is an odorless and colorless solid at room temperature. It is secreted by the male blister beetle and given to the female during the mating. Afterwards the female beetle will cover its eggs with it as a defense against predators. The complete mechanism of the biosynthesis is currently unknown. If cantharidin is ingested, it severely irritates the urinary tract as it is excreted, causing swelling of the genitalia. This can cause a harmful condition known as priapism in men, where an erection lasts more than about four hours.</p>
<p><br clear="left" />
</p>
<p> </p>
<h2><span class="mw-headline">Medical uses</span></h2>
<p>Diluted, it can be used to remove warts<sup id="cite_ref-pmid13519856_0-0" class="reference"><font size="2"><span>[</span>1<span>]</span></font></sup> and tattoos and to treat the small papules of <em>Molluscum contagiosum</em>.<sup id="cite_ref-1" class="reference"><font size="2"><span>[</span>2<span>]</span></font></sup></p>
<p><font size="2"></font></p>
<h3><span class="mw-headline">Medical risks for humans</span></h3>
<p>Its potential for adverse effects has led it to being included in a list of "problem drugs" used by dermatologists.<sup id="cite_ref-pmid456036_2-0" class="reference"><font size="2"><span>[</span>3<span>]</span></font></sup></p>
<p>When ingested by humans, the LD<sub><font size="2">50</font></sub> is around 0.5 mg/kg, with a dose of as little as 10 milligrams being potentially fatal. Ingesting cantharidin can also cause permanent renal damage. Symptoms of cantharidin poisoning include haematuria and abdominal pains.</p>
<p>The extreme toxicity of cantharidin makes any use as an aphrodisiac highly dangerous because it can easily cause death. As a result, it is illegal to sell (or use) cantharidin for this purpose in many countries.</p>
<p> </p>
<h3><span class="mw-headline">Medical risks for animals</span></h3>
<p>Horses are highly sensitive to cantharidin: the LD<sub><font size="2">50</font></sub> for horses is approximately 1 mg/kg of the horse's body weight. Horses may be accidentally poisoned when fed bales of fodder with blister beetles in them.[1]</p>
<p> </p>
<h2><span class="mw-headline">Footnotes</span></h2>
<div style="-moz-column-count: 2; column-count: 2" class="references-small references-column-count references-column-count-2">
<ol class="references">
<li id="cite_note-pmid13519856-0"><strong>^</strong> <cite style="FONT-STYLE: normal" id="CITEREFEpstein_WL.2C_Kligman_AM1958">Epstein WL, Kligman AM (1958). "Treatment of warts with cantharidin". <em>A. M. A. archives of dermatology</em> <strong>77</strong> (5): 508–11. PMID 13519856.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Treatment+of+warts+with+cantharidin&rft.jtitle=A.+M.+A.+archives+of+dermatology&rft.aulast=Epstein+WL%2C+Kligman+AM&rft.au=Epstein+WL%2C+Kligman+AM&rft.date=1958&rft.volume=77&rft.issue=5&rft.pages=508%E2%80%9311&rft_id=info:pmid/13519856&rfr_id=info:sid/en.wikipedia.org:Cantharidin"><span style="DISPLAY: none"> </span></span></li>
<li id="cite_note-1"><strong>^</strong> <cite style="FONT-STYLE: normal" class="web">"Molluscum contagiosum". Merck Manuals. November 2005<span class="printonly">. http://www.merck.com/mmpe/sec10/ch122/ch122b.html</span><span class="reference-accessdate">. Retrieved on 2007-10-21</span>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.btitle=Molluscum+contagiosum&rft.atitle=&rft.date=November+2005&rft.pub=Merck+Manuals&rft_id=http%3A%2F%2Fwww.merck.com%2Fmmpe%2Fsec10%2Fch122%2Fch122b.html&rfr_id=info:sid/en.wikipedia.org:Cantharidin"><span style="DISPLAY: none"> </span></span></li>
<li id="cite_note-pmid456036-2"><strong>^</strong> <cite style="FONT-STYLE: normal" id="CITEREFBinder_R1979">Binder R (1979). "Malpractice--in dermatology". <em>Cutis; cutaneous medicine for the practitioner</em> <strong>23</strong> (5): 663–6. PMID 456036.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Malpractice--in+dermatology&rft.jtitle=Cutis%3B+cutaneous+medicine+for+the+practitioner&rft.aulast=Binder+R&rft.au=Binder+R&rft.date=1979&rft.volume=23&rft.issue=5&rft.pages=663%E2%80%936&rft_id=info:pmid/456036&rfr_id=info:sid/en.wikipedia.org:Cantharidin"><span style="DISPLAY: none"> </span></span></li>
</ol>
</div>
<p> </p>
<h2><span class="mw-headline">External links</span></h2>
<ul>
<li><a class="external text" title="http://www.faidherbe.org/site/cours/dupuis/canthar4.htm" href="http://www.faidherbe.org/site/cours/dupuis/canthar4.htm" rel="nofollow"><font color="#0066cc">Cantharidin</font></a></li>
<li><a class="external text" title="http://www.chm.bris.ac.uk/motm/motm.htm" href="http://www.chm.bris.ac.uk/motm/motm.htm" rel="nofollow"><font color="#0066cc">Molecule of the Month</font></a></li>
</ul>
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<p> </p>
<h2><span class="mw-headline">History</span></h2>
<div class="thumb tleft">
<div style="WIDTH: 152px" class="thumbinner"><img class="thumbimage" border="0" alt="" src="http://upload.wikimedia.org/wikipedia/commons/thumb/2/22/Black_blister_beetle.jpg/150px-Black_blister_beetle.jpg" width="150" height="137" />
<div class="thumbcaption">
<div class="magnify"><img alt="" src="/skins-1.5/common/images/magnify-clip.png" width="15" height="11" /></div>
Black Blister Beetle <em>Epicauta pennsylvanica</em></div>
</div>
</div>
<p>Cantharidin was first isolated by Pierre Robiquet in 1810. It is an odorless and colorless solid at room temperature. It is secreted by the male blister beetle and given to the female during the mating. Afterwards the female beetle will cover its eggs with it as a defense against predators. The complete mechanism of the biosynthesis is currently unknown. If cantharidin is ingested, it severely irritates the urinary tract as it is excreted, causing swelling of the genitalia. This can cause a harmful condition known as priapism in men, where an erection lasts more than about four hours.</p>
<p><br clear="left" />
</p>
<p> </p>
<h2><span class="mw-headline">Medical uses</span></h2>
<p>Diluted, it can be used to remove warts<sup id="cite_ref-pmid13519856_0-0" class="reference"><font size="2"><span>[</span>1<span>]</span></font></sup> and tattoos and to treat the small papules of <em>Molluscum contagiosum</em>.<sup id="cite_ref-1" class="reference"><font size="2"><span>[</span>2<span>]</span></font></sup></p>
<p><font size="2"></font></p>
<h3><span class="mw-headline">Medical risks for humans</span></h3>
<p>Its potential for adverse effects has led it to being included in a list of "problem drugs" used by dermatologists.<sup id="cite_ref-pmid456036_2-0" class="reference"><font size="2"><span>[</span>3<span>]</span></font></sup></p>
<p>When ingested by humans, the LD<sub><font size="2">50</font></sub> is around 0.5 mg/kg, with a dose of as little as 10 milligrams being potentially fatal. Ingesting cantharidin can also cause permanent renal damage. Symptoms of cantharidin poisoning include haematuria and abdominal pains.</p>
<p>The extreme toxicity of cantharidin makes any use as an aphrodisiac highly dangerous because it can easily cause death. As a result, it is illegal to sell (or use) cantharidin for this purpose in many countries.</p>
<p> </p>
<h3><span class="mw-headline">Medical risks for animals</span></h3>
<p>Horses are highly sensitive to cantharidin: the LD<sub><font size="2">50</font></sub> for horses is approximately 1 mg/kg of the horse's body weight. Horses may be accidentally poisoned when fed bales of fodder with blister beetles in them.[1]</p>
<p> </p>
<h2><span class="mw-headline">Footnotes</span></h2>
<div style="-moz-column-count: 2; column-count: 2" class="references-small references-column-count references-column-count-2">
<ol class="references">
<li id="cite_note-pmid13519856-0"><strong>^</strong> <cite style="FONT-STYLE: normal" id="CITEREFEpstein_WL.2C_Kligman_AM1958">Epstein WL, Kligman AM (1958). "Treatment of warts with cantharidin". <em>A. M. A. archives of dermatology</em> <strong>77</strong> (5): 508–11. PMID 13519856.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Treatment+of+warts+with+cantharidin&rft.jtitle=A.+M.+A.+archives+of+dermatology&rft.aulast=Epstein+WL%2C+Kligman+AM&rft.au=Epstein+WL%2C+Kligman+AM&rft.date=1958&rft.volume=77&rft.issue=5&rft.pages=508%E2%80%9311&rft_id=info:pmid/13519856&rfr_id=info:sid/en.wikipedia.org:Cantharidin"><span style="DISPLAY: none"> </span></span></li>
<li id="cite_note-1"><strong>^</strong> <cite style="FONT-STYLE: normal" class="web">"Molluscum contagiosum". Merck Manuals. November 2005<span class="printonly">. http://www.merck.com/mmpe/sec10/ch122/ch122b.html</span><span class="reference-accessdate">. Retrieved on 2007-10-21</span>.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.btitle=Molluscum+contagiosum&rft.atitle=&rft.date=November+2005&rft.pub=Merck+Manuals&rft_id=http%3A%2F%2Fwww.merck.com%2Fmmpe%2Fsec10%2Fch122%2Fch122b.html&rfr_id=info:sid/en.wikipedia.org:Cantharidin"><span style="DISPLAY: none"> </span></span></li>
<li id="cite_note-pmid456036-2"><strong>^</strong> <cite style="FONT-STYLE: normal" id="CITEREFBinder_R1979">Binder R (1979). "Malpractice--in dermatology". <em>Cutis; cutaneous medicine for the practitioner</em> <strong>23</strong> (5): 663–6. PMID 456036.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Malpractice--in+dermatology&rft.jtitle=Cutis%3B+cutaneous+medicine+for+the+practitioner&rft.aulast=Binder+R&rft.au=Binder+R&rft.date=1979&rft.volume=23&rft.issue=5&rft.pages=663%E2%80%936&rft_id=info:pmid/456036&rfr_id=info:sid/en.wikipedia.org:Cantharidin"><span style="DISPLAY: none"> </span></span></li>
</ol>
</div>
<p> </p>
<h2><span class="mw-headline">External links</span></h2>
<ul>
<li><a class="external text" title="http://www.faidherbe.org/site/cours/dupuis/canthar4.htm" href="http://www.faidherbe.org/site/cours/dupuis/canthar4.htm" rel="nofollow"><font color="#0066cc">Cantharidin</font></a></li>
<li><a class="external text" title="http://www.chm.bris.ac.uk/motm/motm.htm" href="http://www.chm.bris.ac.uk/motm/motm.htm" rel="nofollow"><font color="#0066cc">Molecule of the Month</font></a></li>
</ul>
