Cantharidin: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
"Toxic and poisonous" is redundant. "Very definite" is also redundant (something's either definite or not). Plurality fixed. Virulent != violent. Citation is incomplete.
→‎History: full ref
Line 42: Line 42:
|title = Kompendium der Tierärztlichen Homöopathie
|title = Kompendium der Tierärztlichen Homöopathie
|publisher = Enke
|publisher = Enke
|isbn = 978-3432978925 }}</ref>, 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 definite toxic properties comparable in degree to those of the most virulent poisons known in the 19th century, such as [[strychnine]].<ref>Robiquet. M., ''Ann. Chim.'', 1810, vol. 76, pp. 302-307.</ref>{{clarify|date=December 2012|reason=This citation is incomplete. Given title of article, full name of author, full name of journal.}} It is an odorless and colorless solid at [[room temperature]]. It is secreted by the male [[blister beetle]] and given to the female as a copulatory gift 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.
|isbn = 978-3432978925 }}</ref>, 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 definite toxic properties comparable in degree to those of the most virulent poisons known in the 19th century, such as [[strychnine]].<ref>{{cite journal|last=Robiquet|first=Pierre Jean|title=Expériences sur les cantharides|journal=Annales de Chimie|year=1810|volume=76|pages=302-322}}</ref> It is an odorless and colorless solid at [[room temperature]]. It is secreted by the male [[blister beetle]] and given to the female as a copulatory gift 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.


<br clear=left>
<br clear=left>

Revision as of 14:03, 3 December 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[1], 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 definite toxic properties comparable in degree to those of the most virulent poisons known in the 19th century, such as strychnine.[2] It is an odorless and colorless solid at room temperature. It is secreted by the male blister beetle and given to the female as a copulatory gift 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[3][4] and tattoos and to treat the small papules of Molluscum contagiosum.[5]

Medical risks for humans

Its potential for adverse effects has led it to being included in a list of "problem drugs" used by dermatologists[6] and emergency personnel.[7] However, when compounded properly and applied in the clinic topically by a medical provider familiar with its effects and uses, cantharidin can be safe and effective in treating certain selected benign skin lesions like warts and molluscum[8].

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.[6]

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.[9]

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.[10]

Research

Topical treatment with cantharidin appears to have some effect in an animal model of cutaneous leishmaniasis.[11] In addition to topical medical applications, cantharidin and its analogues may have activity against cancer cells.[12][13][14] Laboratory studies with cultured tumor cell lines suggest that this activity may relate to inhibition of protein phosphatase 2A.[15][16]

References

  1. ^ Wolter, Hans (1995). Kompendium der Tierärztlichen Homöopathie. Enke. ISBN 978-3432978925.
  2. ^ Robiquet, Pierre Jean (1810). "Expériences sur les cantharides". Annales de Chimie. 76: 302–322.
  3. ^ Epstein WL, Kligman AM (1958). "Treatment of warts with cantharidin". A. M. A. Archives of dermatology. 77 (5): 508–11. PMID 13519856.
  4. ^ Bacelieri R, Johnson SM (2005). "Cutaneous warts: an evidence-based approach to therapy". Am Fam Physician. 72 (4): 647–52. PMID 16127954. {{cite journal}}: Unknown parameter |month= ignored (help)
  5. ^ "Molluscum contagiosum". Merck Manuals. 2005. Retrieved 2007-10-21. {{cite web}}: Unknown parameter |month= ignored (help)
  6. ^ a b Binder R (1979). "Malpractice--in dermatology". Cutis; cutaneous medicine for the practitioner. 23 (5): 663–6. PMID 456036.
  7. ^ 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)
  8. ^ Moen, L.; Shwayder, T., Chang M. (October 2001). "Cantharidin revisited: a blistering defense of an ancient medicine". Archives of Dermatology (137): 1357–1360.
  9. ^ 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)
  10. ^ "Blister Beetle Poisoning / Cantharidin toxicosis". Retrieved 2010-12-31.
  11. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 20435039, please use {{cite journal}} with |pmid=20435039 instead.
  12. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 21658450, please use {{cite journal}} with |pmid=21658450 instead.
  13. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 12970086, please use {{cite journal}} with |pmid=12970086 instead.
  14. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 20875681, please use {{cite journal}} with |pmid=20875681 instead.
  15. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 19123473, please use {{cite journal}} with |pmid=19123473 instead.
  16. ^ 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=526171443"