14343

1(S),9(R)-(−)-Bicuculline methiodide

≥95.0% (HPCE)

• Synonym(s): (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
• Empirical Formula (Hill Notation): C₂₁H₂₀INO₆
• CAS Number: 40709-69-1
• Molecular Weight: 509.29
• Beilstein/REAXYS Number: 5419649
• MDL number: MFCD00078966
• UNSPSC Code: 12352200
• PubChem Substance ID: 329750456
• NACRES: NA.77

Properties

• 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

Description

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

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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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)