Cantharidin: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
No edit summary
Line 32: Line 32:
}}
}}


'''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.
'''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 contain cantharidin.


==History==
==History==

Revision as of 20:00, 13 June 2012

Cantharidin
Names
IUPAC names
2,6-Dimethyl-4,10-dioxatricyclo-
[5.2.1.02,6]decane-3,5-dione
Other names
Cantharidin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.240 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H12O4/c1-9-5-3-4-6(13-5)10(9,2)8(12)14-7(9)11/h5-6H,3-4H2,1-2H3/t5-,6+,9-,10+ checkY
    Key: DHZBEENLJMYSHQ-YUMGAWCOSA-N checkY
  • O=C2OC([C@@]1(C)[C@@H] 3CC[C@@H](O3)[C@]12C)=O
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).
☒N verify (what is checkY☒N ?)

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 contain cantharidin.

History

Black Blister Beetle Epicauta pennsylvanica

Cantharidin was first isolated in 1810 by Pierre Robiquet, a French chemist then living in Paris, from Lytta vesicatoria. Robiquet demonstrated that cantharidin was the actual principle responsible for the aggressively blistering properties of the coating of the eggs of that insect, and established that cantharidin had very definite toxic and poisonous properties comparable in degree to that of the most violent poisons known in the 19th century, such as strychnine.[1] 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 of cantharidin is currently unknown.


Medical uses

Diluted solutions of cantharidin can be used as a topical medication to remove warts[2] and tattoos and to treat the small papules of Molluscum contagiosum.[3]

Medical risks for humans

Its potential for adverse effects has led it to being included in a list of "problem drugs" used by dermatologists[4] and emergency personnel.[5]

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.[4]

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.[6]

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.[citation needed]

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.[7]

Research

Topical treatment with cantharidin appears to have some effect in an animal model of cutaneous leishmaniasis.[8] In addition to topical medical applications, cantharidin and its analogues may have activity against cancer cells.[9][10][11] Laboratory studies with cultured tumor cell lines suggest that this activity may relate to inhibition of protein phosphatase 2A.[12][13]

References

  1. ^ Robiquet. M., Ann. Chim., 1810, vol. 76, pp. 302-307.
  2. ^ Epstein WL, Kligman AM (1958). "Treatment of warts with cantharidin". A. M. A. Archives of dermatology. 77 (5): 508–11. PMID 13519856.
  3. ^ "Molluscum contagiosum". Merck Manuals. 2005. Retrieved 2007-10-21. {{cite web}}: Unknown parameter |month= ignored (help)
  4. ^ a b Binder R (1979). "Malpractice--in dermatology". Cutis; cutaneous medicine for the practitioner. 23 (5): 663–6. PMID 456036.
  5. ^ 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)
  6. ^ Capinera JL, Gardner DR, Stermitz FR (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)
  7. ^ "Blister Beetle Poisoning / Cantharidin toxicosis". Retrieved 2010-12-31.
  8. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 20435039, please use {{cite journal}} with |pmid=20435039 instead.
  9. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 21658450, please use {{cite journal}} with |pmid=21658450 instead.
  10. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 12970086, please use {{cite journal}} with |pmid=12970086 instead.
  11. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 20875681, please use {{cite journal}} with |pmid=20875681 instead.
  12. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 19123473, please use {{cite journal}} with |pmid=19123473 instead.
  13. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 20331621, please use {{cite journal}} with |pmid=20331621 instead.

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=Cantharidin&oldid=497445025"