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Picrotoxin

Picrotoxin

Picrotoxin: picrotoxinin (left) and picrotin (right)

Picrotoxin
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 124-87-8 Yes
ATC code None
PubChem CID 5360688
DrugBank APRD00269
ChemSpider 16736444 Yes
UNII ZLT174DL7U 
KEGG C09529 
ChEMBL CHEMBL506977 
Chemical data
Formula C30H34O13 
Mol. mass 602.583 g/mol
SMILES eMolecules & PubChem
  • InChI=1S/C15H18O7.C15H16O6/c1-12(2,18)6-7-10(16)20-8(6)9-13(3)14(7,19)4-5-15(13,22-5)11(17)21-9;1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h5-9,18-19H,4H2,1-3H3;6-10,18H,1,4H2,2-3H3/t5-,6+,7-,8-,9-,13-,14-,15+;6-,7+,8-,9-,10-,13-,14-,15+/m11/s1 Yes
    Key:VJKUPQSHOVKBCO-AHMKVGDJSA-N Yes
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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]

Chemical structure

Picrotoxin (C30H34O13) is an equimolar mixture of two compounds, picrotoxinin (C15H16O6) and picrotin (C15H18O7).[4]

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.

References

  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 (1812) "Analyse chimique de la Coque du Levant, Menispermum cocculus," Bulletin de Pharmacie, vol. 4, page 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.

External links

v · d · eNeurotoxins

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Bacterial toxins: Botulinum toxin • Tetanospasmin
Fungal toxins: Bicuculline
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v · d · eGABAergics
Receptor
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Agonists: Main site: Bamaluzole • Gaboxadol • Ibotenic acid • Isoguvacine • Isonipecotic acid • Muscimol (Amanita Muscaria) • Progabide • SL 75102 • Thiomuscimol • Tolgabide; Positive allosteric modulators: Barbiturates • Benzodiazepines • Carbamates • Chlormezanone • Clomethiazole • Ethanol (Alcohol) • Etomidate • Kavalactones (Kava) • Loreclezole • Metomidate • Neuroactive steroids • Nonbenzodiazepines (β-Carbolines, Cyclopyrrolones, Imidazopyridines, Pyrazolopyrimidines, etc.) • Phenols • Piperidinediones • Propanidid • Pyrazolopyridines • Quinazolinones • ROD-188 • Skullcap • Stiripentol • Valerenic acid (Valerian)
* See Template:GABAAergics for a full list of GABAA positive allosteric modulators.

Antagonists: Main site: Bicuculline • Gabazine • Pitrazepin; Negative allosteric modulators: α5IA • Bilobalide • Cicutoxin • Cyclothiazide • DMCM • Flumazenil • Flurothyl • Furosemide • L-655,708 • Oenanthotoxin • Penicillin • Pentylenetetrazol • Picrotoxin • PWZ-029 • Ro15-4513 • Sarmazenil • Suritozole • Thujone (Absinthe) • Thiocolchicoside • ZK-93426

Agonists: Main site: 1,4-Butanediol • Baclofen • GBL • GHB • GHV • GVL • Lesogaberan • Phenibut • Progabide • SKF-97,541 • Tolgabide; Positive allosteric modulators: BHF-177 • BHFF • BSPP • CGP-7930 • GS-39783
Antagonists: Main site: CGP-35348 • Phaclofen • Saclofen • SCH-50911

Agonists: Main site: CACA • CAMP • GABOB • N(4)-chloroacetylcytosine arabinoside • Progabide • Tolgabide
Antagonists: Main site: Bilobalide • TPMPA
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v · d · eGlycinergics
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Bicuculline • Brucine • Caffeine • Picrotoxin • Pitrazepin • Strychnine • Thiocolchicoside • Tutin
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Categories:

  • GABA antagonists
  • Convulsants
  • Lactones

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Look at other dictionaries:

  • Picrotoxin — Pic ro*tox in, n. [Gr. ? bitter + toxic + in.] (Chem.) A bitter white crystalline substance found in the cocculus indicus. It is a peculiar poisonous neurotic and intoxicant, and consists of a mixture of several neutral substances. [1913 Webster] …   The Collaborative International Dictionary of English

  • picrotoxin — [pik΄rō täk′sin] n. [ PICRO + TOXIN] a white, bitter, poisonous, crystalline compound, C30H34O13, resembling strychnine in its properties: used as a stimulant in cases of barbiturate poisoning …   English World dictionary

  • Picrotoxin — Strukturformel Picrotin (oben), Picrotoxinin (unten) …   Deutsch Wikipedia

  • picrotoxin — noun Etymology: International Scientific Vocabulary Date: 1815 a poisonous bitter crystalline stimulant and convulsive substance C30H34O13 obtained from the berry of a southeast Asian vine (Anamirta cocculus) and used intravenously as an antidote …   New Collegiate Dictionary

  • picrotoxin — picrotoxic, adj. /pik reuh tok sin/, n. Pharm. a white, crystalline, bitter, poisonous, central nervous system stimulant, C30H34O13, obtained from the seeds of Anamirta cocculus: used chiefly in the treatment of barbiturate poisoning. [1865 70; …   Universalium

  • picrotoxin — noun A poisonous material, extracted from the seeds of the Anamirta cocculus, used as a stimulant; it is a complex of two alkaloids picrotoxinin and picrotin Syn: cocculin …   Wiktionary

  • picrotoxin — A very bitter neutral principle derived from the fruit of Anamirta cocculus (family Menispermaceae); a central nervous system stimulant, used as an antidote for poisoning by barbiturates and certain other CNS depressant drugs; a convulsant and… …   Medical dictionary

  • picrotoxin — n. type of poison found in plant seeds …   English contemporary dictionary

  • picrotoxin — pic·ro·tox·in …   English syllables

  • picrotoxin — pic•ro•tox•in [[t]ˌpɪk rəˈtɒk sɪn[/t]] n. pha a poisonous stimulant, C30H34O13, obtained from the seeds of Anamirta cocculus, used to treat barbiturate poisoning • Etymology: 1865–70; < Gk pikr(ós) bitter + o +toxin …   From formal English to slang