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(-)-Bicuculline methiodide

Catalog No.
B7081
GABAA receptor antagonist
Grouped product items
SizePriceStock Qty
10mg
$147.00
In stock
50mg
$621.00
Ship with 5-10 days

Tel: +1-832-696-8203

Email: [email protected]

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Background

(-)-Bicuculline methiodide is an antagonist of γ-aminobutyric acid-A (GABAA) receptor, with IC50 value of 500 μM for GABA binding [1]. 

Three classes of GABA receptors have been characterized based on their pharmacology, namely GABAA, GABAB and GABAC receptors, among which GABAA and GABAC receptors are ligand-gated chloride (Cl-) channels. GABA receptors play important roles in central nervous system by responding to the inhibitory neurotransmitter GABA [2]. 

On synaptic membranes of chick cerebellum at birth, (-)-bicuculline methiodide acted as a less potent convulsant than (+)-Bicuculline methiodide which was more effective in displacing GABA binding, with an IC50 value of 10 μM [1]. In C. elegans, (-)-bicuculline methiodide at the concentration of 10 μM did not inhibit UNC-49B homomeric or UNC-49B/C heteromeric receptors which are UNC-49 subunits most closely related to the bicuculline- and benzodiazepine-insensitive RDL GABA receptors of insects. (-)-Bicuculline methiodide was used to confirm that the UNC-49 receptors were pharmacologically distinct from the mammalian GABAA receptors [3]. 

References:

[1]. Fiszer De Plazas S. Ontogenesis of GABA receptor sites in chick embryo cerebellum. Brain Research, 1982, 255(2): 263-275.

[2]. Goutman J D, Calvo D J. Studies on the mechanisms of action of picrotoxin, quercetin and pregnanolone at the GABA rho 1 receptor. British Journal of Pharmacology, 2004, 141(4): 717-727.

[3]. Bamber B A, Twyman R E, Jorgensen E M. Pharmacological characterization of the homomeric and heteromeric UNC-49 GABA receptors in C. elegans. British Journal of Pharmacology, 2003, 138(5): 883-893.

Chemical Properties

Physical AppearanceYellow solid
StorageStore at RT
M.Wt509.3
Cas No.40709-69-1
FormulaC21H20INO6
Solubility<10.19mg/ml in H2O; <25.46mg/ml in DMSO
Chemical Name(S)-6,6-dimethyl-5-((R)-8-oxo-6,8-dihydro-[1,3]dioxolo[4,5-e]isobenzofuran-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide
SDFDownload SDF
Canonical SMILESO=C1O[[email protected]](C(C=C2)=C1C3=C2OCO3)[[email protected]](C4=C5)[N+](C)(C)CCC4=CC6=C5OCO6.[I-]
Shipping ConditionShip with blue ice, or upon other requests.
General tipsFor obtaining a higher solubility, please warm the tube at 37°C and shake it in the ultrasonic bath for a while. We do not recommend long-term storage for the solution, please use it up soon.

Quality Control

Quality Control & MSDS

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Chemical structure

(-)-Bicuculline methiodide