P1675

Picrotoxin

powder

• Synonyma: Cocculin
• Empirický vzorec (Hillův zápis): C₃₀H₃₄O₁₃
• Číslo CAS: 124-87-8
• Molekulová hmotnost: 602.58
• Beilstein/REAXYS Number: 3894406
• EC Number: 204-716-6
• MDL number: MFCD00074824
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278188
• NACRES: NA.77

Vlastnosti

• 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)

Popis

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

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

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.

Features and Benefits

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This compound is featured on the GABAA Receptors and GABAC Receptors pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

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

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

Bezpečnostní informace

• pictograms: GHS06
• signalword: Danger
• hcodes: H300
• pcodes: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 2 Oral
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges