Cantharidin 164670 221230805 2008-06-23T16:59:15Z SpBot 7016748 robot Removing: [[pt:Cantárida]] {{Chembox new | Name = Cantharidin | ImageFile = Cantharidin structure.png | ImageSize = | IUPACName = 2,6-Dimethyl-4,10-dioxatricyclo-<br />[5.2.1.0<sup>2,6</sup>]decane-3,5-dione | OtherNames = Cantharidin | Section1 = {{Chembox Identifiers | CASNo = 56-25-7 | SMILES = O=C2OC([C@@]1(C)[C@@H] 3CC[C@@H](O3)[C@]12C)=O }} | Section2 = {{Chembox Properties | Formula = C<sub>10</sub>H<sub>12</sub>O<sub>4</sub> | MolarMass = 196.20 g/mol | Density = 1.41 g/cm³ | MeltingPt = 212 °C }} }} '''Cantharidin''', a type of [[terpenoid]], is a [[poison]]ous [[chemical compound]] secreted by many species of [[blister beetle]], and most notably by the [[Spanish fly]], ''Lytta vesicatoria''. The [[Oedemeridae|false blister beetles]] and [[Pyrochroidae|cardinal beetles]] also have cantharidin. ==History== [[Image:Black blister beetle.jpg|left|thumb|150px|Black Blister Beetle ''Epicauta pennsylvanica'']] 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. <br clear=left> ==Medical uses== Diluted, it can be used to remove [[wart]]s,<ref name="pmid13519856">{{cite journal |author=Epstein WL, Kligman AM |title=Treatment of warts with cantharidin |journal=A. M. A. archives of dermatology |volume=77 |issue=5 |pages=508–11 |year=1958 |pmid=13519856 |doi=}}</ref> [[tattoo]]s and to treat the small papules of ''[[Molluscum contagiosum]]''.<ref>{{cite web |title=Molluscum contagiosum |url=http://www.merck.com/mmpe/sec10/ch122/ch122b.html |date=November 2005 |publisher=Merck Manuals |accessdate=2007-10-21}}</ref> ===Medical risks=== Its potential for adverse effects have led it to being included in a list of "problem drugs" used by dermatologists.<ref name="pmid456036">{{cite journal |author=Binder R |title=Malpractice--in dermatology |journal=Cutis; cutaneous medicine for the practitioner |volume=23 |issue=5 |pages=663–6 |year=1979 |pmid=456036 |doi=}}</ref> When [[ingestion|ingested]] by humans, the [[LD50|LD<sub>50</sub>]] 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== {{reflist|2}} ==External links== * [http://www.faidherbe.org/site/cours/dupuis/canthar4.htm Cantharidin] * [http://www.chm.bris.ac.uk/motm/motm.htm Molecule of the Month] [[Category:Ethers]] [[Category:Acid anhydrides]] [[Category:Terpenes and terpenoids]] [[de:Cantharidin]] [[es:Cantaridina]] [[fr:Cantharidine]] [[ja:カンタリジン]] [[no:Cantharidin]] [[pl:Kantarydyna]] [[ru:Кантаридин]]