Picrotoxin

• Catalog No.: DB00466
• CAS Number: 124-87-8
• M. F.: C30H34O13
• M. W.: 602.58316

SYNONYMS

• IUPAC name: (1R,3R,5S,8S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione; (1R,5S,8S,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione
• IUPAC Traditional name: (1R,3R,5S,8S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione; (1R,5S,8S,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione
• Brand Name: Oriental berry; Cocculin; Cocculine; Coques du levant; Cocculus; Fish berry; Indian berry

DATABASE IDS

• CAS Number: 124-87-8
• PubChem SID: 46506796
• PubChem CID: 31304

PROPERTIES

• Hydrophobicity(logP): -2.229
• Solubility: 4100 mg/L

DETAILS

Description (English)

• Drug Groups: approved
• Description: A noncompetitive antagonist at GABA-A receptors and thus a convulsant. Picrotoxin blocks the gamma-aminobutyric acid-activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially the barbiturates. [PubChem]
• Indication: Used internally for relieving respiratory distress. Also for use as an antidote in poisoning by CNS depressants, especially barbiturates.
• Pharmacology: Picrotoxin is a toxin obtained from the seeds of the shrub Anamirta cocculus. It is used as a central nervous system stimulant, antidote, convulsant, and GABA (gamma aminobutyric acid) antagonist. It is a noncompetitive antagonist at GABA_A receptors and thus a convulsant. Picrotoxin blocks the GABA_Activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially barbiturates.
• Toxicity: Oral, mouse: LD₅₀ = 15 mg/kg. In large doses it is a powerful poison, causing unconsciousness, delirium, convulsions, gastro-enteritis and stimulation of the respiratory centre followed by paralysis, from which death sometimes results.
• Affected Organisms: Humans and other mammals
• References: [Link] ; Ehrenberger K, Benkoe E, Felix D: Suppressive action of picrotoxin, a GABA antagonist, on labyrinthine spontaneous nystagmus and vertigo in man. Acta Otolaryngol. 1982 Mar-Apr;93(3-4):269-73. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Link
• Ehrenberger K, Benkoe E, Felix D: Suppressive action of picrotoxin, a GABA antagonist, on labyrinthine spontaneous nystagmus and vertigo in man. Acta Otolaryngol. 1982 Mar-Apr;93(3-4):269-73. Pubmed