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Cantharidin
From Wikipedia, the free encyclopedia
| 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, a type of terpenoid, 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 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 irritates the urinary tract as it is excreted, causing swelling of the genetalia. This can cause a harmful condition known as priapism in men, where an erection lasts more than about four hours.
Diluted, it can be used to remove warts and tattoos.[citation needed] In addition, it can be used to treat the small papules of Molluscum contagiosum. However, when ingested by humans, the LD50 is around 0.5 mg/kg, with a dose of as little as 10 mg being potentially fatal. This makes the use of canthadarin as an aphrodisiac highly dangerous and it is illegal to sell it for this purpose in many countries.