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Submit Review(-)-Bicuculline methochloride
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)
Biological Activity for (-)-Bicuculline methochloride
(-)-Bicuculline methochloride is a 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 for (-)-Bicuculline methochloride
| M. Wt | 417.85 |
| Formula | C21H20ClNO6 |
| Storage | Store at RT |
| Purity | ≥99% (HPLC) |
| CAS Number | 38641-83-7 |
| 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 for (-)-Bicuculline methochloride
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 41.78 | 100 |
Preparing Stock Solutions for (-)-Bicuculline methochloride
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 for (-)-Bicuculline methochloride
References for (-)-Bicuculline methochloride
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
If you know of a relevant reference for (-)-Bicuculline methochloride, please let us know.
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Keywords: (-)-Bicuculline methochloride, (-)-Bicuculline methochloride supplier, Water-soluble, GABAA, antagonists, Receptors, 0131, Tocris Bioscience
23 Citations for (-)-Bicuculline methochloride
Citations are publications that use Tocris products. Selected citations for (-)-Bicuculline methochloride include:
Dong et al (2018) CAST/ELKS Proteins Control Voltage-Gated Ca2+ Channel Density and Synaptic Release Probability at a Mammalian Central Synapse. Cell Rep 24 284 PMID: 29996090
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
Tushev et al (2018) Alternative 3' UTRs Modify the Localization, Regulatory Potential, Stability, and Plasticity of mRNAs in Neuronal Compartments. Neuron 98 495 PMID: 29656876
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
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
Dilger et al (2015) Absence of plateau potentials in dLGN cells leads to a breakdown in retinogeniculate refinement. J Neurosci 35 3652 PMID: 25716863
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
Sigler et al (2017) Formation and Maintenance of Functional Spines in the Absence of Presynaptic Glutamate Release. Neuron 94 304 PMID: 28426965
Vida and Frotscher (2000) A hippocampal interneuron associated with the mossy fiber system. Proc Natl Acad Sci U S A 97 1275 PMID: 10655521
Wagner et al (2019) Myosin VI Drives Clathrin-Mediated AMPA Receptor Endocytosis to Facilitate Cerebellar Long-Term Depression. Cell Rep 28 11 PMID: 31269433
Shao et al (2003) Spontaneous synaptic activity is primarily GABAergic in vestibular nucleus neurons of the chick embryo. J Neurophysiol 90 1182 PMID: 12904504
Lai et al (2017) Molecular Mechanisms of Synaptic Vesicle Priming by Munc13 and Munc18. Neuron 95 591 PMID: 28772123
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
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
Pati et al (2020) Chronic postnatal chemogenetic activation of forebrain excitatory neurons evokes persistent changes in mood behavior ELife 9 PMID: 32955432
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Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
*Please note that Tocris will only send literature to established scientific business / institute addresses.
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