1,3-Dioxolo(4,5-g)isoquinolinium, 5-((6R)-6,8-dihydro-8-oxofuro(3,4-e)-1,3-benzodioxol-6-yl)-5,6,7,8-tetrahydro-6,6-dimethyl-, iodide (1:1), (5S)-
Basic information
- CAS
40709-69-1- Standard SMILES
C[N+]1(C)CCc2cc3c(cc2[C@H]1[C@@H]1OC(=O)c2c1ccc1c2OCO1)OCO3.[I-]- InChIKey
HKJKCPKPSSVUHY-GRTNUQQKSA-M- Molecular formula
- C21H20INO6
- Average molar mass
- 509.3 g/mol
- Monoisotopic mass
- 509.03353
Names & identifiers
- Preferred name
- 1,3-Dioxolo(4,5-g)isoquinolinium, 5-((6R)-6,8-dihydro-8-oxofuro(3,4-e)-1,3-benzodioxol-6-yl)-5,6,7,8-tetrahydro-6,6-dimethyl-, iodide (1:1), (5S)-
- IUPAC
- (6R)-6-[(5S)-6,6-dimethyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-ium-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one iodide
- English name
- (-)-Bicucullinemethiodide
- Molecular formula
- C21H20INO6
- Molecular weight
- 0
Names & synonyms
Bicuculline methiodide40709-69-1RefChem:4075201,3-Dioxolo(4,5-g)isoquinolinium, 5-((6R)-6,8-dihydro-8-oxofuro(3,4-e)-1,3-benzodioxol-6-yl)-5,6,7,8-tetrahydro-6,6-dimethyl-, iodide (1:1), (5S)-(+)-Bicuculline methiodideMLS000069548(6R)-6-[(5S)-6,6-dimethyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-ium-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one;iodideSMR000058804(-)-BicucullinemethiodideMLS001148459MFCD00078966DTXSID60873651
Show more names
(-)-Bicuculline methiodide(?)-Bicuculline methiodide(-)-Bicuculline methiodide, GABAA antagonist1(S),9(R)-(?)-Bicuculline methiodide( ) Bicuculline methiodide,()Bicuculline methiodide(-)-Bicuculline methiodide (mM/ml), GABAA antagonist(-)-Bicuculline methiodide DISCONTINUED. offer B382505(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
Properties
Computed structural properties
- Topological polar surface area
- 63.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 1
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 655
Experimental & physicochemical properties
Solubility>76.4 [ug/mL] (The mean of the results at pH 7.4)
Physicochemical properties
- RTECS
- 4904100 · JI4904100
- storage temp.
- Store at RT
- solubility
- 2 O: · H2O: soluble10mg/mL, almost clear, greenish-yellow
- form
- Pale yellow solid.
- color
- Yellow
- optical activity
- -117 · [α]/D -117±7°, c = 1 in chloroform
- Water Solubility
- 2 O: · H2O: 10mg/mL, almost clear, greenish-yellow
- BRN
- 5419649 · 5419649
- InChIKey
- HKJKCPKPSSVUHY-GRTNUQQKSA-M
- SMILES
- [I-].[H][C@]1(OC(=O)c2c3OCOc3ccc12)[C@]4([H])c5cc6OCOc6cc5CC[N+]4(C)C
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 6 · GHS06,GHS09
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 1 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS06,GHS09
- hazard_class
- 6.1
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H301-H311-H330-H400
- Precautionary statements
- P301+P310a-P304+P340-P320-P330-P405-P501a
Chemistry & industry
Applications
Uses1(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).
General DescriptionBicuculline is a phthalide isoquinoline alkaloid, which is extracted from Dicentra cucullaria. It acts as an acetylcholinesteraseinhibitor. Bicuculline inhibits slow afterhyperpolarization (AHP).
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…