P1675

Picrotoxin

GABAA receptor antagonist, powder

• Sinónimos: Cocculin
• Fórmula empírica (notación de Hill): C₃₀H₃₄O₁₃
• Número CAS: 124-87-8
• Peso molecular: 602.58
• NACRES: NA.77
• PubChem Substance ID: 24278188
• UNSPSC Code: 12352200
• EC Number: 204-716-6
• MDL number: MFCD00074824
• Beilstein/REAXYS Number: 3894406
• Form: powder

Propiedades

• Nombre del producto: Picrotoxin, powder
• form: powder
• Quality Segment: 200
• 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)

Descripción

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

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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

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

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

Información de seguridad

• pictograms: GHS06
• signalword: Danger
• hcodes: H300
• pcodes: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 2 Oral
• Clase de almacenamiento: 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
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges