Cantharidin: Difference between revisions
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Revision as of 12:02, 6 August 2010
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| Names | |
|---|---|
| IUPAC names
2,6-Dimethyl-4,10-dioxatricyclo-
[5.2.1.02,6]decane-3,5-dione | |
| Other names
Cantharidin
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| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.000.240 |
CompTox Dashboard (EPA)
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| Properties | |
| C10H12O4 | |
| Molar mass | 196.20 g/mol |
| Density | 1.41 g/cm³ |
| Melting point | 212 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 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.
Medical uses
Diluted solutions of cantharidin can be used as a topical medication to remove warts[1] and tattoos and to treat the small papules of Molluscum contagiosum.[2]
Medical risks for humans
Its potential for adverse effects has led it to being included in a list of "problem drugs" used by dermatologists[3] and emergency personnel.[4]
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 initially cause severe damage to the lining of the gastrointestinal and urinary tract, and may also cause permanent renal damage. Symptoms of cantharidin poisoning include haematuria, abdominal pains, and rarely priapism.[3]
The level of cantharidin in blister beetles can be quite variable: Among blister beetles of the genus Epicauta in Colorado, E. pennsylvanica contain approximately 0.2 mg, E. maculata contain 0.7 mg, and E. immaculata contain 4.8 mg per beetle; males also contain higher levels than females.[5]
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.[1]
Footnotes
- ^ Epstein WL, Kligman AM (1958). "Treatment of warts with cantharidin". A. M. A. Archives of dermatology. 77 (5): 508–11. PMID 13519856.
- ^ "Molluscum contagiosum". Merck Manuals. 2005. Retrieved 2007-10-21.
{{cite web}}: Unknown parameter|month=ignored (help) - ^ a b Binder R (1979). "Malpractice--in dermatology". Cutis; cutaneous medicine for the practitioner. 23 (5): 663–6. PMID 456036.
- ^ Karras DJ, Farrell SE, Harrigan RA, Henretig FM, Gealt L (1996). "Poisoning from "Spanish fly" (cantharidin)". Am J Emerg Med. 14 (5): 478–83. doi:10.1016/S0735-6757(96)90158-8. PMID 8765116.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ Authors: Capinera, J. L.; Gardner, D. R.; Stermitz, F. R. (1985-10). "Cantharidin Levels in Blister Beetles (Coleoptera: Meloidae) Associated with Alfalfa in Colorado". Journal of Economic Entomology. 78 (5): 1052–1055.
{{cite journal}}: Check date values in:|date=(help)CS1 maint: multiple names: authors list (link)