(-)-Bicuculline methiodide

Pricing Availability Delivery Time Qty
Cat.No. 2503 - (-)-Bicuculline methiodide | C21H20INO6 | CAS No. 40709-69-1
Description: Water-soluble GABAA antagonist
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 iodide
Purity: ≥99% (HPLC)
Datasheet
Citations (25)
Literature

Biological Activity

Methiodide form of classical GABAA receptor antagonist (+)-bicuculline (Cat. No. 0130). More water-soluble and stable. Non-GABA receptor-mediated actions reported, including actions on calcium-dependent potassium channels.

Technical Data

M. Wt 509.3
Formula C21H20INO6
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 40709-69-1
PubChem ID 104871
InChI Key HKJKCPKPSSVUHY-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.[I-]

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

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 25.46 50
water 10.19 20

Preparing Stock Solutions

The following data is based on the product molecular weight 509.3. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.96 mL 9.82 mL 19.63 mL
5 mM 0.39 mL 1.96 mL 3.93 mL
10 mM 0.2 mL 0.98 mL 1.96 mL
50 mM 0.04 mL 0.2 mL 0.39 mL

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

Product Datasheets

Certificate of Analysis / Product Datasheet
Select another batch:
Safety Datasheet

References

References are publications that support the products' biological activity.

Olsen et al (1976) Studies on the neuropharmacological activity of bicuculline and related compounds. Brain Res. 102 283 PMID: 1247886

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

Chan et al (2006) Blockade of GABA(A) receptors in the ventromedial hypothalamus further stimulates glucagon and sympathoadrenal but not the hypothalamo-pituitary-adrenal response to hypoglycemia. Diabetes 55 1080 PMID: 16567532

Kurt et al (2006) Differential effects of iontophoretic in vivo application of the GABAA-antagonists bicuculline and gabazine in sensory cortex. Hear.Res. 212 224 PMID: 16442250


If you know of a relevant reference for (-)-Bicuculline methiodide, please let us know.

View Related Products by Target

View Related Products by Product Action

View all GABAA Receptor Antagonists

Keywords: Water-soluble GABAA antagonists Receptors GABAA Receptors

25 Citations for (-)-Bicuculline methiodide

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

Zemkova et al (2011) Norepinephrine causes a biphasic change in mammalian pinealocye membrane potential: role of alpha1B-adrenoreceptors, phospholipase C, and Ca2+. Endocrinology 152 3842 PMID: 21828176

Gallo and Iadecola (2011) Neuronal nitric oxide contributes to neuroplasticity-associated protein expression through cGMP, protein kinase G, and extracellular signal-regulated kinase. J Neurosci 31 6947 PMID: 21562256

Lussier et al (2011) Activity-dependent ubiquitination of the AMPA receptor subunit GluA2. Pharmacol Res Perspect 31 3077 PMID: 21414928

Jackson et al (2010) Control of cerebellar long-term potentiation by P-Rex-family guanine-nucleotide exchange factors and phosphoinositide 3-kinase. PLoS One 5 e11962 PMID: 20694145

Terasaki et al (2010) Activation of NR2A receptors induces ischemic tolerance through CREB signaling. J Cereb Blood Flow Metab 30 1441 PMID: 20145658

Bortone and Polleux (2009) KCC2 expression promotes the termination of cortical interneuron migration in a voltage-sensitive calcium-dependent manner. Neuron 62 53 PMID: 19376067

Prat et al (2009) Mutation of the protein kinase C site in borna disease virus phosphoprotein abrogates viral interference with neuronal signaling and restores normal synaptic activity. Neuroscience 5 e1000425 PMID: 19424436

Wayman et al (2008) An activity-regulated microRNA controls dendritic plasticity by down-regulating p250GAP. PLoS One 105 9093 PMID: 18577589

Young et al (2007) Glutamate receptor expression and chronic glutamate toxicity in rat motor cortex. Neurobiol Dis 26 78 PMID: 17240155

Volmer et al (2007) Borna disease virus infection impairs synaptic plasticity. J Biol Chem 81 8833 PMID: 17553893

Cichon and Gan (2015) Branch-specific dendritic Ca(2+) spikes cause persistent synaptic plasticity. Nature 520 180 PMID: 25822789

Fehérvári et al (2015) In Vivo Voltage-Sensitive Dye Study of Lateral Spreading of Cortical Activity in Mouse Primary Visual Cortex Induced by a Current Impulse. PLoS One 10 e0133853 PMID: 26230520

Rioult-Pedotti et al (2015) Dopamine Promotes Motor Cortex Plasticity and Motor Skill Learning via PLC Activation. J Neurosci 10 e0124986 PMID: 25938462

Ootsuka and Mohammed (2015) Activation of the habenula complex evokes autonomic physiological responses similar to those associated with emotional stress. J Virol 3 PMID: 25677551

Kempf et al (2014) The sphingolipid receptor S1PR2 is a receptor for Nogo-a repressing synaptic plasticity. PLoS Biol 12 e1001763 PMID: 24453941

Pedroni et al (2014) Electrophysiological characterization of granule cells in the dentate gyrus immediately after birth. Front Cell Neurosci 8 44 PMID: 24592213

Tashiro et al (2014) GABAergic influence on temporomandibular joint-responsive spinomedullary neurons depends on estrogen status. Proc Natl Acad Sci U S A 259 53 PMID: 24316475

Zhang et al (2014) Glycine induces bidirectional modifications in N-methyl-D-aspartate receptor-mediated synaptic responses in hippocampal CA1 neurons. PLoS Pathog 289 31200 PMID: 25231980

He and Bausch (2014) Synaptic plasticity in glutamatergic and GABAergic neurotransmission following chronic memantine treatment in an in vitro model of limbic epileptogenesis. J Neurophysiol 77 379 PMID: 24184417

Benton et al (2013) Iberiotoxin-sensitive and -insensitive BK currents in Purkinje neuron somata. J Neurophysiol 109 2528 PMID: 23446695

Janczewski et al (2013) Role of inhibition in respiratory pattern generation. J Neurosci 33 5454 PMID: 23536061

He et al (2013) Synaptic and extrasynaptic plasticity in glutamatergic circuits involving dentate granule cells following chronic N-methyl-D-aspartate receptor inhibition. Neuroscience 109 1535 PMID: 23255721

Wagner et al (2013) The dorsomedial hypothalamus mediates stress-induced hyperalgesia and is the source of the pronociceptive peptide cholecystokinin in the rostral ventromedial medulla. Physiol Rep 238 29 PMID: 23415792

Platt et al (2012) Striatal dopamine transmission is subtly modified in human A53Tα-synuclein overexpressing mice. PLoS One 7 e36397 PMID: 22570709

He et al (2012) Increased Kv1 channel expression may contribute to decreased sIPSC frequency following chronic inhibition of NR2B-containing NMDAR. Neuropsychopharmacology 37 1338 PMID: 22218089


Do you know of a great paper that uses (-)-Bicuculline methiodide from Tocris? If so please let us know.

Commented out for usability testing

Reviews

TODO: Add Reviews

Literature in this Area

Pain

Pain Research Product Guide

A collection of over 250 products for pain research, the guide includes research tools for the study of:

  • Nociception
  • Ion Channels
  • G-Protein-Coupled Receptors
  • Intracellular Signaling
GABA Receptors

GABA Receptors Scientific Review

Written by Ian Martin, Norman Bowery and Susan Dunn, this review provides a history of the GABA receptor, as well as discussing the structure and function of the various subtypes and the clinical potential of receptor modulators; compounds available from Tocris are listed.

Addiction

Addiction Poster

The key feature of drug addiction is the inability to stop using a drug despite clear evidence of harm. This poster describes the brain circuits associated with addiction, and provides an overview of the main classes of addictive drugs and the neurotransmitter systems that they target.

Pain

Pain Poster

Peripheral sensitization is the reduction in the threshold of excitability of sensory neurons that results in an augmented response to a given external stimulus. This poster outlines the excitatory and inhibitory signaling pathways involved in modulation of peripheral sensitization. The role of ion channels, GPCRs, neurotrophins, and cytokines in sensory neurons are also described.

Schizophrenia

Schizophrenia Poster

Schizophrenia is a debilitating psychiatric disorder that affects 1% of the worldwide population. This poster highlights the targets and pathways representing the most promising strategies to pursue for novel drug development.

Pathways for (-)-Bicuculline methiodide

Protocols

TODO: Add Protocols