Picrotoxin

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Picrotoxin
Picrotoxin, chemical (line) structure.png
Picrotoxin 3D sticks.png
Picrotoxinin (left) and picrotin (right)
Clinical data
Legal status ?
Identifiers
CAS number 124-87-8 YesY
ATC code None
PubChem CID 5360688
IUPHAR ligand 4051
DrugBank DB00466
ChemSpider 16736444 YesY
UNII ZLT174DL7U YesY
KEGG C09529 N
ChEMBL CHEMBL506977 YesY
Chemical data
Formula ?
 N (what is this?)  (verify)

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 the fruit of the climbing plant Anamirta cocculus, it has a strong physiological action. It acts as a non-competitive channel blocker for the GABAA receptor chloride channels.[3] 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.[4]

Chemical structure[edit]

Picrotoxin is an equimolar mixture of two compounds, picrotoxinin (C15H16O6) and picrotin (C15H18O7).[5]

Other uses[edit]

Picrotoxin is classified as an illegal performance-enhancing "Class 1 substance" by the American Quarter Horse Association.

References[edit]

  1. ^ Boullay, P. F. G. (1812). "Analyse chimique de la Coque du Levant, Menispermum cocculus". Bulletin de Pharmacie (in French) 4: 1–34.  (Note: "Menispermum cocculus" has been renamed "Anamirta cocculus".)
  2. ^ Boullay, P. F. G. (1812). "Analyse chimique de la Coque du Levant, Menispermum cocculus". Bulletin de Pharmacie (in French) 4: 31.  (Note: "Menispermum cocculus" has been renamed "Anamirta cocculus".)
  3. ^ Rho JM, Donevan SD, Rogawski MA (1996). "Direct activation of GABA-A receptors by barbiturates in cultured rat hippocampal neurons". J Physiol 497 (2): 509-522. PMC 1161000. PMID 8961191. 
  4. ^ Nilsson, E.; Eyrich, B. (1950). "On Treatment of Barbiturate Poisoning". Acta Medica Scandinavica 137 (6): 381–389. doi:10.1111/j.0954-6820.1950.tb12129.x. PMID 15432128.  edit
  5. ^ "Picrotoxin". Catalog. Sigma Aldrich. 

External links[edit]