(-)-Bicuculline methiodide

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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 (37)
Reviews
Literature

Biological Activity

Methiodide form of classical GABAA receptor antagonist (+)-bicuculline. More water-soluble and stable. Non-GABA receptor-mediated actions reported, including actions on calcium-dependent potassium channels.

Methobromide Salt and Methochloride Salt also available.

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
water 10.19 20
DMSO 25.46 50

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.

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

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

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

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


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Keywords: (-)-Bicuculline methiodide, (-)-Bicuculline methiodide supplier, Water-soluble, GABAA, antagonists, Receptors, 2503, Tocris Bioscience

37 Citations for (-)-Bicuculline methiodide

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

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

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

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

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

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

Ahsan Raza (2017) HIPP neurons in the dentate gyrus mediate the cholinergic modulation of background context memory salience. Nat Commun 8 189 PMID: 28775269

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

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

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

Zhang et al (2014) Dopamine preferentially inhibits NMDA receptor-mediated EPSCs by acting on presynaptic D1 receptors in nucleus accumbens during postnatal development. PLoS One 9 e86970 PMID: 24784836

Zhang et al (2016) Increased Activity of Src Homology 2 Domain Containing Phosphotyrosine Phosphatase 2 (Shp2) Regulates Activity-dependent AMPA Receptor Trafficking. J Biol Chem 291 18856 PMID: 27417137

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

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

Huang and Hsu (2010) Activation of muscarinic acetylcholine receptors induces a nitric oxide-dependent long-term depression in rat medial prefrontal cortex. Cereb Cortex 20 982 PMID: 19666830

Ferando et al (2016) Diminished KCC2 confounds synapse specificity of LTP during senescence. Nat Neurosci 19 1197 PMID: 27500406

Kohnomi et al (2012) D(2)-like dopamine receptors differentially regulate unitary IPSCs depending on presynaptic GABAergic neuron subtypes in rat nucleus accumbens shell. J Neurophysiol 107 692 PMID: 22049335

Zhu et al (2012) Inflammation-induced shift in spinal GABA(A) signaling is associated with a tyrosine kinase-dependent increase in GABA(A) current density in nociceptive afferents. J Neurophysiol 108 2581 PMID: 22914654

Kim et al (2012) Decreased afferent excitability contributes to synaptic depression during high-frequency stimulation in hippocampal area CA1. J Neurophysiol 108 1965 PMID: 22773781

Chan et al (2004) HCN2 and HCN1 channels govern the regularity of autonomous pacemaking and synaptic resetting in globus pallidus neurons. J Neurosci 24 9921 PMID: 15525777

Owen and Grover (2015) Activity-dependent differences in function between proximal and distal Schaffer collaterals. J Neurophysiol 113 3646 PMID: 25855695

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

Song et al (2012) Restoration of intracortical and thalamocortical circuits after transplantation of bone marrow mesenchymal stem cells into the ischemic brain of mice. Cell Transplant 22 2001 PMID: 23069268

Pennock and Hentges (2011) Differential expression and sensitivity of presynaptic and postsynaptic opioid receptors regulating hypothalamic proopiomelanocortin neurons. J Neurosci 31 281 PMID: 21209213

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

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

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

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

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

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


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