(-)-Bicuculline methochloride

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Cat.No. 0131 - (-)-Bicuculline methochloride | C21H20ClNO6 | CAS No. 53552-05-9
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 chloride
Purity: ≥99% (HPLC)
Datasheet
Citations (18)
Reviews (1)
Literature

Biological Activity

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

Methoiodide Salt and Methobromide Salt also available.

Technical Data

M. Wt 417.85
Formula C21H20ClNO6
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 53552-05-9
PubChem ID 10047593
InChI Key RLJKFAMYSYWMND-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.[Cl-]

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 41.78 100

Preparing Stock Solutions

The following data is based on the product molecular weight 417.85. 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
1 mM 2.39 mL 11.97 mL 23.93 mL
5 mM 0.48 mL 2.39 mL 4.79 mL
10 mM 0.24 mL 1.2 mL 2.39 mL
50 mM 0.05 mL 0.24 mL 0.48 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.

Kemp et al (1986) Quantitative evaluation of the potencies of GABA-receptor agonists and antagonists using the rat hippocampal slice preparation. Br.J.Pharmacol. 87 677 PMID: 3011168

Seutin et al (1997) Evidence for a non-GABAergic action of quaternary salts of bicuculline on DArgic neurones. Neuropharmacology 36 1653 PMID: 9517436

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


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Keywords: (-)-Bicuculline methochloride, (-)-Bicuculline methochloride supplier, Water-soluble, GABAA, antagonists, Receptors, 0131, Tocris Bioscience

18 Citations for (-)-Bicuculline methochloride

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

Lai et al (2017) Molecular Mechanisms of Synaptic Vesicle Priming by Munc13 and Munc18. Neuron 95 591 PMID: 28772123

Dilger et al (2011) Requirements for synaptically evoked plateau potentials in relay cells of the dorsal lateral geniculate nucleus of the mouse. J Physiol 589 919 PMID: 21173075

Dilger et al (2015) Absence of plateau potentials in dLGN cells leads to a breakdown in retinogeniculate refinement. J Neurosci 35 3652 PMID: 25716863

Couchman et al (2011) Lateral superior olive function in congenital deafness. Hear Res 277 163 PMID: 21276842

Karst et al (2010) Metaplasticity of amygdalar responses to the stress hormone corticosterone. Proc Natl Acad Sci U S A 107 14449 PMID: 20663957

Woo et al (2007) Neuregulin-1 enhances depolarization-induced GABA release. Neuron 54 599 PMID: 17521572

Nateri et al (2007) ERK activation causes epilepsy by stimulating NMDA receptor activity. EMBO J 26 4891 PMID: 17972914

Kelm et al (2007) Calcium release from presynaptic internal stores is required for ethanol to increase spontaneous γ-aminobutyric acid release onto cerebellum Purkinje neurons. J Pharmacol Exp Ther 323 356 PMID: 17652632

Rojas et al (2013) Activation of group I metabotropic glutamate receptors potentiates heteromeric kainate receptors. Mol Pharmacol 83 106 PMID: 23066089

Ly et al (2013) T-type channel blockade impairs long-term potentiation at the parallel fiber-Purkinje cell synapse and cerebellar learning. Proc Natl Acad Sci U S A 110 20302 PMID: 24277825

Nelson and Glitsch (2012) Lack of kinase regulation of canonical transient receptor potential 3 (TRPC3) channel-dependent currents in cerebellar Purkinje cells. J Biol Chem 287 6326 PMID: 22207762

Glitsch (2010) Activation of native TRPC3 cation channels by phospholipase D. FASEB J 24 318 PMID: 19741172

Choe et al (2015) High salt intake increases blood pressure via BDNF-mediated downregulation of KCC2 and impaired baroreflex inhibition of vasopressin neurons. Neuron 85 549 PMID: 25619659

Angelantonio et al (2015) Basal adenosine modulates the functional properties of AMPA receptors in mouse hippocampal neurons through the activation of A1R A2AR and A3R. Front Cell Neurosci 9 409 PMID: 26528137

Erkens et al (2015) Protein tyrosine phosphatase receptor type R is required for Purkinje cell responsiveness in cerebellar long-term depression. Mol Brain 8 1 PMID: 25571783

Jaiswal et al (2015) Reduction in focal ictal activity following transplantation of MGE interneurons requires expression of the GABAA receptor α4 subunit. Front Cell Neurosci 9 127 PMID: 25914623

Shao et al (2003) Spontaneous synaptic activity is primarily GABAergic in vestibular nucleus neurons of the chick embryo. J Neurophysiol 90 1182 PMID: 12904504

Vida and Frotscher (2000) A hippocampal interneuron associated with the mossy fiber system. Proc Natl Acad Sci U S A 97 1275 PMID: 10655521


Do you know of a great paper that uses (-)-Bicuculline methochloride from Tocris? Please let us know.

Reviews for (-)-Bicuculline methochloride

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Increased excitability with GABAA antagonism: Excellent publishable, performed ideally.
By Anonymous on 10/20/2017
Assay Type: In Vitro
Species: Rat
Cell Line/Tissue: Organotypic Hippocampus Slices

Bath application of Bicuculline methochloride increased overall excitation of neurons in slice.

PMID: 28185854

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