- Cantharidin
Chembox new
Name = Cantharidin
ImageFile = Cantharidin structure.png
ImageSize =
IUPACName = 2,6-Dimethyl-4,10-dioxatricyclo-
[5.2.1.02,6] 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 = C10H12O4
MolarMass = 196.20 g/mol
Density = 1.41 g/cm³
MeltingPt = 212 °CCantharidin, a type of
terpenoid , is apoison ouschemical compound secreted by many species ofblister beetle , and most notably by theSpanish 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 atroom temperature . It is secreted by the maleblister 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 thebiosynthesis is currently unknown. If cantharidin is ingested, it severely irritates theurinary tract as it is excreted, causing swelling of the genitalia. This can cause a harmful condition known aspriapism in men, where an erection lasts more than about four hours.Medical uses
Diluted, it can be used to remove
wart s,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=]tattoo s and to treat the small papules of "Molluscum contagiosum ". [cite web |title=Molluscum contagiosum |url=http://www.merck.com/mmpe/sec10/ch122/ch122b.html |month=November | year=2005 |publisher=Merck Manuals |accessdate=2007-10-21]Medical risks for humans
Its potential for adverse effects have led it to being included in a list of "problem drugs" used by dermatologists.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=]
When ingested by humans, the LD50 is around 0.5 mg/kg, with a dose of as little as 10
milligrams being potentially fatal. Ingesting cantharidin can also cause permanentrenal damage. Symptoms of cantharidin poisoning includehaematuria and abdominal pains. The extreme toxicity of cantharidin makes any use as anaphrodisiac 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.Medical risks for animals
Horses are highly sensitive to cantharidin: the LD50 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. [http://www.addl.purdue.edu/newsletters/2006/Fall/EquineCT.htm]
Footnotes
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]
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