14343

1(S),9(R)-(−)-Bicuculline methiodide

≥95.0% (HPCE)

• Synonyme(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
• Formule empirique (notation de Hill): C₂₁H₂₀INO₆
• Numéro CAS: 40709-69-1
• Poids moléculaire : 509.29
• Numéro Beilstein : 5419649
• Numéro MDL: MFCD00078966
• Code UNSPSC : 12352200
• ID de substance PubChem : 329750456
• Nomenclature NACRES : NA.77

Propriétés

• Pureté: ≥95.0% (HPCE)
• Forme: powder
• Activité optique: [α]/D -117±7°, c = 1 in chloroform
• Solubilité: H₂O: 10 mg/mL, almost clear, greenish-yellow
• Température de stockage: 2-8°C
• Chaîne 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
• Clé InChI: HKJKCPKPSSVUHY-GRTNUQQKSA-M

Description

Description générale

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).

Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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Notes préparatoires

hergestellt aus (+)-Bicucullin

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)