P1675

Picrotoxin

powder

• Synonym(s): Cocculin
• Empirical Formula (Hill Notation): C₃₀H₃₄O₁₃
• CAS Number: 124-87-8
• Molecular Weight: 602.58
• Beilstein: 3894406
• EC Number: 204-716-6
• MDL number: MFCD00074824
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278188
• NACRES: NA.77

Properties

• form: powder
• color: white
• mp: 203 °C (lit.)
• SMILES string: [H][C@@]12C[C@@]3(O)[C@@]4([H])[C@H](C(C)=C)[C@]([H])(OC4=O)[C@@]5([H])OC(=O)[C@]1(O2)[C@@]35C.[H][C@@]67C[C@@]8(O)[C@@]9([H])[C@@H]([C@]([H])(OC9=O)[C@@]%10([H])OC(=O)[C@]6(O7)[C@@]8%10C)C(C)(C)O
• 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
• InChI key: VJKUPQSHOVKBCO-NGKRNLQBSA-N
• Gene Information: human ... GABRA1(2554) , GABRA2(2555) , GABRA3(2556) , GABRA4(2557) , GABRA5(2558) , GABRA6(2559) , GABRB1(2560) , GABRB2(2561) , GABRB3(2562)

Description

General description

Picrotoxin is isolated from moonseed family, Menispermaceae. It is a stimulant and may cause convulsions. It is an allosteric modulator of γ-aminobutyric acid (GABA_A) receptor.

Application

Picrotoxin has been used:

• as non-competitive antagonist for the γ-aminobutyric acid (GABA_A) for studying synchronized burst (SB) dynamics
• as a component of extracellular saline for blocking glutamate and acetylcholine receptors in neurons
• as a component of artificial cerebrospinal fluid (ACSF) for voltage-clamp recordings studies in dissociated cortical neurons

Biochem/physiol Actions

Picrotoxin is a competitive inhibitor of glycine receptors (GlyRs). It is a non-competitive antagonist, which binds to ligand bounded γ-aminobutyric acid (GABAA) receptor.

GABA_A receptor antagonist; binds to the GABA receptor-linked Cl⁻ channel.

Features and Benefits

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Other Notes

Molecular complex (1:1) of picrotin and picrotoxinin.

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H300
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 2 Oral
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves