14343

1(S),9(R)-(−)-Bicuculline methiodide

≥95.0% (HPCE), GABAA receptor antagonist, powder

• 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 CAS: 40709-69-1
• Peso molecular: 509.29
• NACRES: NA.77
• PubChem Substance ID: 329750456
• UNSPSC Code: 12352200
• MDL number: MFCD00078966
• Beilstein/REAXYS Number: 5419649
• Assay: ≥95.0% (HPCE)
• Form: powder

Propiedades

• Nombre del producto: 1(S),9(R)-(−)-Bicuculline methiodide, ≥95.0% (HPCE)
• Quality Segment: 100
• assay: ≥95.0% (HPCE)
• form: powder
• optical activity: [α]/D -117±7°, c = 1 in chloroform
• solubility: H₂O: 10 mg/mL, almost clear, greenish-yellow
• storage temp.: 2-8°C
• SMILES string: [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
• InChI key: HKJKCPKPSSVUHY-GRTNUQQKSA-M

Descripción

General description

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

Application

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).

Biochem/physiol Actions

(-)-Bicuculline methiodide is a GABAA receptor antagonist, which acts as a competitive inhibitor of GABA ligand binding to the 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 Potassium Channels pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

prepared from (+)-bicuculline

Información de seguridad

• Clase de almacenamiento: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)