14343

1(S),9(R)-(−)-Bicuculline methiodide

≥95.0% (HPCE)

• Sinónimos: (5S)-5-[(6R)-6,8-Dihydro-8-oxofuro[3,4-e]-1,3-benzodioxol-6-yl]-5,6,7,8-tetrahydro-6,6-dimethyl-1,3-dioxolo[4,5-g]isoquinolinium iodide
• Fórmula empírica (notación de Hill): C₂₁H₂₀INO₆
• Número de CAS: 40709-69-1
• Peso molecular: 509.29
• Beilstein: 5419649
• Número MDL: MFCD00078966
• Código UNSPSC: 12352200
• ID de la sustancia en PubChem: 329750456
• NACRES: NA.77

Propiedades

• Análisis: ≥95.0% (HPCE)
• formulario: powder
• actividad óptica: [α]/D -117±7°, c = 1 in chloroform
• solubilidad: H₂O: 10 mg/mL, almost clear, greenish-yellow
• temp. de almacenamiento: 2-8°C
• cadena SMILES: [I-].[H][C@]1(OC(=O)c2c3OCOc3ccc12)[C@]4([H])c5cc6OCOc6cc5CC[N+]4(C)C
• InChI: 1S/C21H20NO6.HI/c1-22(2)6-5-11-7-15-16(26-9-25-15)8-13(11)18(22)19-12-3-4-14-20(27-10-24-14)17(12)21(23)28-19;/h3-4,7-8,18-19H,5-6,9-10H2,1-2H3;1H/q+1;/p-1/t18-,19+;/m0./s1
• Clave InChI: HKJKCPKPSSVUHY-GRTNUQQKSA-M

Descripción

Descripción general

Bicuculline is a phthalide isoquinoline alkaloid, which is extracted from Dicentra cucullaria. It acts as an acetylcholinesterase inhibitor. Bicuculline inhibits slow afterhyperpolarization (AHP).

Aplicación

1(S),9(R)-(-)-Bicuculline methiodide has been used as a gamma-aminobutyric acid (GABA) antagonist to block inhibition in the semicoronal slices. It has also been used for the preparation of organotypic hippocampal slice cultures (OHSCs).

Acciones bioquímicas o fisiológicas

(-)-Bicuculline methiodide is a GABAA receptor antagonist, which acts as a competitive inhibitor of GABA ligand binding to the receptor.

Características y beneficios

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 Potassium Channels pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Nota de preparación

hergestellt aus (+)-Bicucullin

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: Eyeshields, Gloves, type N95 (US)