14343

1(S),9(R)-(−)-Bicuculline methiodide

≥95.0% (HPCE)

• Sinônimo(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
• Fórmula empírica (Notação de Hill): C₂₁H₂₀INO₆
• Número CAS: 40709-69-1
• Peso molecular: 509.29
• Beilstein: 5419649
• Número MDL: MFCD00078966
• Código UNSPSC: 12352200
• ID de substância PubChem: 329750456
• NACRES: NA.77

Propriedades

• Nível de qualidade: 100
• Ensaio: ≥95.0% (HPCE)
• Formulário: powder
• atividade óptica: [α]/D -117±7°, c = 1 in chloroform
• solubilidade: H₂O: 10 mg/mL, almost clear, greenish-yellow
• temperatura de armazenamento: 2-8°C
• cadeia de caracteres 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
• chave InChI: HKJKCPKPSSVUHY-GRTNUQQKSA-M

Descrição

Descrição geral

Bicuculline is a phthalide isoquinoline alkaloid, which is extracted from Dicentra cucullaria.[1] It acts as an acetylcholinesterase inhibitor.[2] Bicuculline inhibits slow afterhyperpolarization (AHP).[3]

Aplicação

1(S),9(R)-(-)-Bicuculline methiodide has been used as a gamma-aminobutyric acid (GABA) antagonist to block inhibition in the semicoronal slices.[4] It has also been used for the preparation of organotypic hippocampal slice cultures (OHSCs).[5]

Ações bioquímicas/fisiológicas

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

Características e benefícios

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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.

Nota de preparo

prepared from (+)-bicuculline

Informações de segurança

• Código de classe de armazenamento: 11 - Combustible Solids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable
• Equipamento de proteção individual: Eyeshields, Gloves, type N95 (US)