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Picrotoxin: picrotoxinin (left) and picrotin (right)
Picrotoxin
Systematic (IUPAC) name
 ?
Identifiers
CAS number 124-87-8
ATC code none
PubChem 5360688
DrugBank APRD00269
Chemical data
Formula C 30H34O13  
Mol. mass 602.583 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

Picrotoxin,[1] also known as cocculin, is a poisonous crystalline plant compound, first isolated by Boullay in 1812.[2]

Found primarily in Cocculus indicus and Anamirta cocculus, it has a strong physiological action. It acts as a non-competitive antagonist for the GABAA receptor chloride channels. It is therefore a channel blocker rather than a receptor antagonist. As GABA itself is an inhibitory neurotransmitter, infusion of picrotoxin has stimulant and convulsant effects.

Chemical structure

Picrotoxin (C30H34O13) consists of two substances, picrotoxinin (C15H1606) and picrotin (C15H1807).[3]

References

  1. ^ The name "picrotoxin" is a combination of the Greek words "picros" (bitter) and "toxicon" (poison) [Boullay (1812), page 31].
  2. ^ Pierre F. G. Boullay, "Analyse chimique de la Coque du Levant, Menispermum cocculus," Bulletin de Pharmacie, vol. 4, pages 1-34 (1812). [Note: Menispermum cocculus has been renamed Anamirta cocculus.]
  3. ^ Chemical structure of picrotoxin is available here: http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=P1675%7CSIGMA&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC .
  • L. Dupont, O. Dideberg, J. Lamotte-Brasseur et L. Angenot (1976). "Structure cristalline et moléculaire de la picrotoxine, C15H16O6.C15H18O 7". Acta Cryst. B32: 2987–2993.   (in French)

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1911 encyclopedia

Up to date as of January 14, 2010

From LoveToKnow 1911

PICROTOXIN, a neutral principle obtained from the Cocculus indicus, which is the fruit of the Anamirta paniculata. It is used in medicine externally as an antiparasitic. Internally it has been successfully used to check the night-sweats of phthisis. In large doses it is a powerful poison, causing unconsciousnes s,, delirium, convulsions, gastro-enteritis and stimulation of the respiratory centre followed by paralysis, from which death sometimes results. Formerly low class publicans sometimes added Cocculus indicus berries to beer to increase the intoxicating effects. Its chemical formula is C1511-1606.1120.


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