Cantharidin

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 °C

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 severely 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,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=] tattoos 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 permanent renal damage. Symptoms of cantharidin poisoning include haematuria and abdominal pains. The extreme toxicity of cantharidin makes any use as an aphrodisiac 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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Look at other dictionaries:

  • Cantharidin — Can*thar i*din (k[a^]n*th[a^]r [i^]*d[i^]n), n. (Chem.) The active principle of the cantharis, or Spanish fly, a volatile, acrid, bitter solid, crystallizing in four sided prisms. [1913 Webster] …   The Collaborative International Dictionary of English

  • Cantharidin — vgl. Kantharidin …   Das Wörterbuch medizinischer Fachausdrücke

  • Cantharidin — Strukturformel Allgemeines Name Cantharidin Andere Namen …   Deutsch Wikipedia

  • Cantharidin — Can|tha|ri|din 〈n.; s; unz.; fachsprachl.〉 = Kantharidin * * * Can|tha|ri|din [griech. kántharis = Spanische Fliege (Käfer, Zool.); ↑ in (3)], das; s: aus einem Käfer isolierbare giftige, tricycl. Verb., die als Hyperämikum u. Vesikans wirkt. * * …   Universal-Lexikon

  • cantharidin — The active principle of cantharis; the anhydride of cantharic acid. SYN: cantharis camphor. * * * can·thar·i·din kan thar əd ən n a bitter crystalline compound C10H12O4 that is the active blister producing ingredient of cantharides * * * n. the… …   Medical dictionary

  • cantharidin — n. the active principle of cantharides, or Spanish fly (the dried bodies of a blister beetle, Lytta vesicatoria). A toxic and irritant chemical, cantharidin causes blistering of the skin and was formerly used in veterinary medicine as a… …   The new mediacal dictionary

  • cantharidin poisoning — poisoning of horses or ruminants by hay contaminated with blister beetles whose bodies contain cantharidin; signs include hyperemia or erosions of the oral and esophageal mucosa, frequent urination, and sometimes shock and death. Called also… …   Medical dictionary

  • cantharidin — noun Date: 1819 a bitter crystalline compound C10H12O4 that is the active blister producing ingredient of cantharides …   New Collegiate Dictionary

  • cantharidin — n. [Gr. kantharis, blister beetle] A chemical produced by adults of the family Meloidae that causes skin blisters; the drug is obtained for medical use from the southern European Lytta vesicatoria, commonly known as Spanish fly …   Dictionary of invertebrate zoology

  • cantharidin — can·thar·i·din (kăn thărʹĭ dĭn) n. A bitter crystalline compound, C10H12O4, that is the active ingredient of cantharides and produces blistering of the skin. * * * …   Universalium

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