Cantharidin: Difference between revisions
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[[image:Cantharidin.png|right|]] |
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! {{chembox header}}| '''{{{name|{{PAGENAME}}}}}''' |
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| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Cantharidin structure.png|150px|{{PAGENAME}}]] |
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| [[IUPAC nomenclature|Chemical name]] |
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| {{{IUPAC|2,6-Dimethyl-4,10-dioxatricyclo-<br>[5.2.1.0<sup>2,6</sup>]decane-3,5-dione}}} |
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| Other names |
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| Cantharidin |
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| [[Chemical formula]] |
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| {{{formula|C<sub>10</sub>H<sub>12</sub>O<sub>4</sub>}}} |
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| [[Molecular mass]] |
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| {{{mol_mass|196.20}}} g/mol |
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| [[CAS registry number|CAS number]] |
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| [{{{CAS|56-25-7}}}] |
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| [[Density]] |
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| {{{density|1.41}}} g/cm<sup>3</sup> |
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| [[Melting point]] |
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| {{{melting_point|212}}} °C |
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| [[Simplified molecular input line entry specification|SMILES]] |
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| {{{SMILES|O=C2OC([C@@]1(C)[C@@H]3<br>CC[C@@H](O3)[C@]12C)=O}}} |
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| {{chembox header}} | <small>[[wikipedia:Chemical infobox|Disclaimer and references]]</small> |
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'''Cantharidin''' is a [[poison]]ous [[chemical compound]] secreted by many species of [[blister beetle]], and most notably by the [[Spanish fly]], ''Lytta vesicatoria''. |
'''Cantharidin''' is a [[poison]]ous [[chemical compound]] secreted by many species of [[blister beetle]], and most notably by the [[Spanish fly]], ''Lytta vesicatoria''. |
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* [http://www.chm.bris.ac.uk/motm/motm.htm Molecule of the Month]. |
* [http://www.chm.bris.ac.uk/motm/motm.htm Molecule of the Month]. |
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[[Category: |
[[Category:Ethers]] |
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[[Category:Acid anhydrides]] |
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[[de:Cantharidin]] |
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Revision as of 15:02, 21 June 2006
| Cantharidin | |
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| Chemical name | 2,6-Dimethyl-4,10-dioxatricyclo- [5.2.1.02,6]decane-3,5-dione |
| Other names | Cantharidin |
| Chemical formula | C10H12O4 |
| Molecular mass | 196.20 g/mol |
| CAS number | [56-25-7] |
| Density | 1.41 g/cm3 |
| Melting point | 212 °C |
| SMILES | O=C2OC([C@@]1(C)[C@@H]3 CC[C@@H](O3)[C@]12C)=O |
| Disclaimer and references | |
Cantharidin is a poisonous chemical compound secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria.
Cantharidin was first isolated by Pierre Robiquet in 1810. It is an odorless and colorless solid at the 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 by human males, as it is excreted by the kidneys, it irritates the urinary tract causing spectacular swelling, called priapism, but this is quite painful and does not result in arousal.
Diluted, it can be used to remove warts and tattoos. In addition, it can be used to treat the small papules of Molluscum contagiosum. However, when ingested 10 mg is usually a fatal dose.