(-)-Bicuculline methobromide

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Cat.No. 0109 - (-)-Bicuculline methobromide | C21H20BrNO6 | CAS No. 73604-30-5
Description: GABAA antagonist; more water soluble version of (+)-bicuculline (Cat. No. 0130)
Chemical Name: [R-(R*,S*)]-5-(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 bromide
Purity: ≥98% (HPLC)
Datasheet
Citations (14)
Reviews (1)
Literature

Biological Activity

Methobromide salt of (+)-bicuculline. Water soluble and more stable than bicuculline. Non-GABA receptor-mediated actions reported.

Methoiodide Salt and Methochloride Salt also available.

Technical Data

M. Wt 462.3
Formula C21H20BrNO6
Storage Store at RT
Purity ≥98% (HPLC)
CAS Number 73604-30-5
PubChem ID 6852386
InChI Key BWXCECYGGMGBHD-GRTNUQQKSA-M
Smiles [H][C@](C(C=CC6=C5OCO6)=C5C(O4)=O)4[C@]2([H])C1=CC3=C(OCO3)C=C1CC[N+](C)2C.[Br-]

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
water 23.11 50

Preparing Stock Solutions

The following data is based on the product molecular weight 462.3. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.5 mM 4.33 mL 21.63 mL 43.26 mL
2.5 mM 0.87 mL 4.33 mL 8.65 mL
5 mM 0.43 mL 2.16 mL 4.33 mL
25 mM 0.09 mL 0.43 mL 0.87 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Bowery et al (1983) Characteristics of GABAB receptor binding sites on rat whole brain synaptic membranes. Br.J.Pharmacol. 78 191 PMID: 6297646

Seutin and Johnson (1999) Recent advances in the pharmacology of quaternary salts of bicuculline. TiPS 20 268 PMID: 10390643

Sperber et al (1987) Nigral infusions of muscimol or bicuculline facilitate seizures in developing rats. Brain Res. 465 243 PMID: 3440204


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Keywords: (-)-Bicuculline methobromide, (-)-Bicuculline methobromide supplier, Water-soluble, GABAA, antagonists, Receptors, 0109, Tocris Bioscience

14 Citations for (-)-Bicuculline methobromide

Citations are publications that use Tocris products. Selected citations for (-)-Bicuculline methobromide include:

Woo et al (2019) Pharmacological Dissection of Intrinsic Optical Signal Reveals a Functional Coupling between Synaptic Activity and Astrocytic Volume Transient. Exp Neurobiol 28 30 PMID: 30853822

Miyazato et al (2008) GABA receptor activation in the lumbosacral spinal cord decreases detrusor overactivity in spinal cord injured rats. J Urol 179 1178 PMID: 18206170

Johnson et al (2011) Activation of group II metabotropic glutamate receptors induces long-term depression of excitatory synaptic transmission in the substantia nigra pars reticulata. Neurosci Lett 504 102 PMID: 21945652

Peng et al (2010) Postsynaptic spiking homeostatically induces cell-autonomous regulation of inhibitory inputs via retrograde signaling. J Neurosci 30 16220 PMID: 21123568

Galván et al (2010) Critical involvement of postsynaptic protein kinase activation in long-term potentiation at hippocampal mossy fiber synapses on CA3 interneurons. J Neurosci 30 2844 PMID: 20181582

Gascon et al (2006) GABA regulates dendritic growth by stabilizing lamellipodia in newly generated interneurons of the olfactory bulb. J Neurosci 26 12956 PMID: 17167085

Andrade-Talavera et al (2016) Presynaptic Spike Timing-Dependent Long-Term Depression in the Mouse Hippocampus. Cereb Cortex 26 3637 PMID: 27282393

Galván et al (2015) Synapse-specific compartmentalization of signaling cascades for LTP induction in CA3 interneurons. Neuroscience 290 332 PMID: 25637803

Maguire et al (2014) Extrasynaptic glycine receptors of rodent dorsal raphe serotonergic neurons: a sensitive target for ethanol. Neuropsychopharmacology 39 1232 PMID: 24264816

Sipilä et al (2009) Compensatory enhancement of intrinsic spiking upon NKCC1 disruption in neonatal hippocampus. J Neurosci 29 6982 PMID: 19474325

Krook-Magnuson et al (2008) Tonically active inhibition selectively controls feedforward circuits in mouse barrel cortex. J Neurophysiol 100 932 PMID: 18509076

Huang and Hessler Social modulation during songbird courtship potentiates midbrain DArgic neurons. PLoS One 3 e3281 PMID: 18827927

Chen et al (2017) Distinct Inhibitory Circuits Orchestrate Cortical beta and gamma Band Oscillations. Neuron 96 1403 PMID: 29268099

Maccione et al (2014) Following the ontogeny of retinal waves: pan-retinal recordings of population dynamics in the neonatal mouse. J Physiol 592 1545 PMID: 24366261


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Bicuculline as an antagonist of alpha2 glycine receptor.
By Anonymous on 05/20/2019
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: HEK-293

Apart of classical action at GABA-A receptors, bicuculline methobromide (BIC) can be used as a tool to reveal presence of alpha2 glycine receptor (GlyR) subunit.In our work we transfected HEK cells with alpha2 and beta GlyR subunits to obtain heteromeric GlyRs. Application of glycine triggered a clear receptors response, but subsequent addition of BIC decreased response amplitude by >95% (see image). This confirmed expression of alpha2 subunits and their incorporation into active GlyRs.

PMID: 30875431
review image

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