Synonym: (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
CAS Number: 40709-69-1
Empirical Formula (Hill Notation): C21H20INO6
Molecular Weight: 509.29
MDL Number: MFCD00078966
Linear Formula: C21H20INO6
Product Type: Chemical
| assay |
≥95.0% (HPCE) |
| form |
powder |
| 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 |
| optical activity |
[α]/D -117±7°, c = 1 in chloroform |
| Quality Level |
100  |
| SMILES string |
[I-].[H][C@]1(OC(=O)c2c3OCOc3ccc12)[C@]4([H])c5cc6OCOc6cc5CC[N+]4(C)C |
| solubility |
H2O: 10 mg/mL, almost clear, greenish-yellow |
| storage temp. |
2-8°C |
| 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 . |
| Features and Benefits: |
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 . |
| 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). |
| Preparation Note: |
prepared from (+)-bicuculline |
| RIDADR |
NONH for all modes of transport |
| WGK Germany |
WGK 3 |
| Flash Point(F) |
Not applicable |
| Flash Point(C) |
Not applicable |
| Purity |
≥95.0% (HPCE) |
| Storage Temp. |
2-8°C |
| UNSPSC |
12352200 |
