Picrotoxin

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File:Picrotoxin, chemical (line) structure.png
Picrotoxin: picrotoxinin (left) and picrotin (right)
Picrotoxin
File:Picrotoxin 3D sticks.png
Identifiers
CAS Number 124-87-8
ATC code none
PubChem CID 5360688
DrugBank APRD00269
Chemical data
Formula C30H34O13
Molar mass 602.583 g/mol[[Script error: No such module "String".]]
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Picrotoxin, also known as cocculin, is a poisonous crystalline plant compound, first isolated by Pierre Boullay in 1812.[1] The name "picrotoxin" is a combination of the Greek words "picros" (bitter) and "toxicon" (poison).[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. As such, picrotoxin can be used to counter barbiturate poisoning, that can occur during general anesthesia or during a large intake outside of the hospital.[3]

Chemical structure

Picrotoxin (C30H34O13) consists of two substances, picrotoxinin (C15H1606) and picrotin (C15H1807).[4]

References

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External links

  • Ehrenberger K, Benkoe E, Felix D (1982). "Suppressive action of picrotoxin, a GABA antagonist, on labyrinthine spontaneous nystagmus and vertigo in man". Acta Otolaryngol. 93 (3-4): 269–73. doi:10.3109/00016488209130882. PMID 7064710. 
  • L. Dupont, O. Dideberg, J. Lamotte-Brasseur et L. Angenot (1976). "Structure cristalline et moléculaire de la picrotoxine, C15H16O6.C15H18O7". Acta Cryst. B32: 2987–2993 (in French). 
  • Basic Neurochemistry: GABA Receptor Physiology and Pharmacology.


Neurotransmitters: Dopamine • Glutamate; Dopamine Precursors: L-Tyrosine • L-Phenylalanine • L-DOPA (Levodopa); Glutamate Precursors: L-Glutamine; NDRAs: Amphetamine • Lisdexamfetamine • Methamphetamine; SNDRAs: αET • αMT • MBDB • MDA • MDEA • MDMA (Ecstasy) • PBA • PCA • PIA; GHBR Agonists: 1,4-BD • GBL • GHB; NMDAR Agonists: Ibotenic Acid; NMDAR Antagonists: Dextromethorphan (DXM) • Dextrorphan (DXO) • Dizocilpine (MK-801) • Ketamine • Phencyclidine (PCP); GABAAR Antagonists: Bicuculline • Picrotoxin; Serotonin-Related: 5,7-DHT; Dopamine-Related: 6-OHDA • MPTP/MPP+ • Norsalsolinol • Rotenone; Others: Batrachotoxin • Ethanol (Alcohol) • Penitrem A
de:Picrotoxin

fr:Picrotoxine nl:Picrotoxine ja:ピクロトキシン

pl:Pikrotoksyna
  1. ↑ 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".)
  2. ↑ Pierre F. G. Boullay, "Analyse chimique de la Coque du Levant, Menispermum cocculus," Bulletin de Pharmacie, vol. 4, p. 31.
  3. ↑ On Treatment of Barbiturate Poisoning, Nilson & Eyrich Acta Medica Scandinavica Volume 137 Issue 6, Pages 381-389.
  4. ↑ 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.
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