Picrotoxin
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| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 124-87-8  |
| ATC code | None |
| PubChem | CID 5360688 |
| DrugBank | APRD00269 |
| ChemSpider | 16736444 |
| UNII | ZLT174DL7U |
| KEGG | C09529  |
| ChEMBL | CHEMBL506977 |
| Chemical data | |
| Formula | C30H34O13 |
| Mol. mass | 602.583 g/mol |
| SMILES | eMolecules & PubChem |
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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 the fruit of the climbing plant Anamirta cocculus, it has a strong physiological action. It acts as a noncompetitive 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]
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[edit] Chemical structure
Picrotoxin (C30H34O13) is an equimolar mixture of two compounds, picrotoxinin (C15H16O6) and picrotin (C15H18O7).[4]
[edit] Other uses
Picrotoxin is classified as an illegal performance-enhancing "Class 1 substance" by the American Quarterhorse Association. The recommended penalty for a first offense is a one-year suspension and a $10,000 fine.
[edit] References
- ^ Boullay, P. F. G. (1812). "Analyse chimique de la Coque du Levant, Menispermum cocculus" (in French). Bulletin de Pharmacie 4: 1–34. http://books.google.com/books?id=pgE4AAAAMAAJ&pg=PA5#v=onepage&q&f=false. (Note: "Menispermum cocculus" has been renamed "Anamirta cocculus".)
- ^ Boullay, P. F. G. (1812). "Analyse chimique de la Coque du Levant, Menispermum cocculus" (in French). Bulletin de Pharmacie 4: 31. http://books.google.com/books?id=pgE4AAAAMAAJ&pg=PA31#v=onepage&q&f=false. (Note: "Menispermum cocculus" has been renamed "Anamirta cocculus".)
- ^ 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.
- ^ "Picrotoxin". Catalog. Sigma Aldrich. http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=P1675%7CSIGMA&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC..
[edit] 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 Oto-Laryngologica 93 (3–4): 269–273. doi:10.3109/00016488209130882. PMID 7064710. http://informahealthcare.com/doi/abs/10.3109/00016488209130882.
- Dupont, L.; Dideberg, O.; Lamotte-Brasseur, J.; Angenot, L. (1976). "Structure cristalline et moléculaire de la picrotoxine, C15H16O6.C15H18O7" (in French). Acta Crystallografica B32: 2987–2993.
- Siegel G. J.; Agranoff, B. W.; Albers, R. W. et al., ed. (1999). "GABA Receptor Physiology and Pharmacology". Basic Neurochemistry: Molecular, Cellular and Medical Aspects (6th ed.). Philadelphia, PA, USA: Lippincott-Raven. http://www.ncbi.nlm.nih.gov/books/bv.fcgi?rid=bnchm.section.1181.
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