Cantharidin
IUPAC name	2,6-Dimethyl-4,10-dioxatricyclo- [5.2.1.02,6]decane-3,5-dione
Other names	Cantharidin
Identifiers
CAS number	[56-25-7]
SMILES	O=C2OC([C@@]1(C)[C@@H] 3CC[C@@H](O3)[C@]12C)=O
Properties
Molecular formula	C10H12O4
Molar mass	196.20 g/mol
Density	1.41 g/cm³
Melting point	212 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox 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. The false blister beetles and cardinal beetles also have cantharidin.

History

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 genitalia. This can cause a harmful condition known as priapism in men, where an erection lasts more than about four hours.

Medical uses

Diluted, it can be used to remove warts,^[1] tattoos and to treat the small papules of Molluscum contagiosum.^[2]

Medical risks

Its potential for adverse effects have led it to being included in a list of "problem drugs" used by dermatologists.^[3]

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 cantharidin as an aphrodisiac highly dangerous and it is illegal to sell it for this purpose in many countries.

Footnotes

External links

• Cantharidin
• Molecule of the Month

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Source: adapted by the editor from Wikipedia, the free encyclopedia; from the article "Cantharidin". Image Credit.

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