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(-)-Bicuculline methiodide

Catalog #: 2503
51 Citations Datasheet / COA / SDS
Catalog # Availability Size / Price Qty
2503/10
2503/50
(-)-Bicuculline methiodide | CAS No. 40709-69-1 | GABA-A Receptor Antagonists
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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 iodide

Purity: ≥99%

Product Details
Citations (51)
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Biological Activity Technical Data Additional Information Background Product Datasheets Calculators

Biological Activity

(-)-Bicuculline methiodide is a 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
Solubility:
Soluble to 20 mM in water and to 50 mM in DMSO
Purity:
≥99%
Storage:
Store at RT
CAS No:
40709-69-1

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.

Additional Information

Other Product-Specific Information:

Background References

  1. The sphingolipid receptor S1PR2 is a receptor for Nogo-a repressing synaptic plasticity.
    Kempf A, Tews B, Arzt M, Weinmann O, Obermair F, Pernet V, Zagrebelsky M, Delekate A, Iobbi C, Zemmar A, Ristic Z, Gullo M, Spies P, Dodd D, Gygax D, Korte M, Schwab M
    PLoS Biol, 2014;12(1):e1001763.
  2. High-throughput genotoxicity assay identifies antioxidants as inducers of DNA damage response and cell death.
    Fox JT, Sakamuru S, Huang R
    Proc. Natl. Acad. Sci. U.S.A., 2012;109(14):5423-8.
  3. Nutritional state-dependent ghrelin activation of vasopressin neurons via retrograde trans-neuronal-glial stimulation of excitatory GABA circuits.
    Haam J, Halmos K, Di S, Tasker J
    J Neurosci, 2014;34(18):6201-13.
  4. Role of GABAA-Mediated Inhibition and Functional Assortment of Synapses onto Individual Layer 4 Neurons in Regulating Plasticity Expression in Visual Cortex.
    Saez I, Friedlander M
    PLoS ONE, 2016;11(2):e0147642.
  5. Studies on the neuropharmacological activity of bicuculline and related compounds.
    Olsen et al.
    Brain Res., 1976;102:283
  6. Recent advances in the pharmacology of quaternary salts of bicuculline.
    Seutin and Johnson
    TiPS, 1999;20:268
  7. Blockade of GABA(A) receptors in the ventromedial hypothalamus further stimulates glucagon and sympathoadrenal but not the hypothalamo-pituitary-adrenal response to hypoglycemia.
    Chan et al.
    Diabetes, 2006;55:1080
  8. Differential effects of iontophoretic in vivo application of the GABAA-antagonists bicuculline and gabazine in sensory cortex.
    Kurt et al.
    Hear.Res., 2006;212:224

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Citations for (-)-Bicuculline methiodide

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

51 Citations: Showing 1 - 10

  1. NMDAR-Activated PP1 Dephosphorylates GluN2B to Modulate NMDAR Synaptic Content.
    Authors: Chiu Et al.
    Cell Rep  2019;28:332
  2. KA metabolite (2R,6R)-hydroxynorKA enhances aggression via periaqueductal gray glutamatergic transmission.
    Authors: Ye Et al.
    Neuropharmacology  2019;157
  3. Wilm's tumor 1 promotes memory flexibility.
    Authors: Mariottini Et al.
    Nat Commun  2019;10:3756
  4. Salicylate-Induced Suppression of Electrically Driven Activity in Brain Slices from the Auditory Cortex of Aging Mice.
    Authors: Namikawa Et al.
    Front Aging Neurosci  2018;9:395
  5. Functional Divergence of Delta and Mu Opioid Receptor Organization in CNS Pain Circuits.
    Authors: Wang Et al.
    Neuron  2018;98:90
  6. Neuronal Activity and Intracellular Calcium Levels Regulate Intracellular Transport of Newly Synthesized AMPAR.
    Authors: Hangen Et al.
    Cell Rep  2018;24:1001
  7. (2R,6R)-hydroxynorKA rescues chronic stress-induced depression-like behavior through its actions in the midbrain periaqueductal gray.
    Authors: Chou Et al.
    Neuropharmacology  2018;139:1
  8. Initiation of Behavioral Response to Antidepressants by Cholecystokinin Neurons of the Dentate Gyrus.
    Authors: Medrihan Et al.
    Neuron  2017;95:564
  9. A Brainstem-Spinal Cord Inhibitory Circuit for Mechanical Pain Modulation by GABA and Enkephalins.
    Authors: Francois Et al.
    Neuron  2017;93:822
  10. HIPP neurons in the dentate gyrus mediate the cholinergic modulation of background context memory salience.
    Authors: Ahsan Raza
    Nat Commun  2017;8(1):189
  11. Amygdalar endothelin-1 regulates pyramidal neuron excitability and affects anxiety.
    Authors: Chen Et al.
    Sci Rep  2017;7:2316
  12. Differential Desensitization Observed at Multiple Effectors of Somatic μ-Opioid Receptors Underlies Sustained Agonist-Mediated Inhibition of Proopiomelanocortin Neuron Activity.
    Authors: Fox and Hentges
    J Neurosci  2017;37:8667
  13. Src homology 2 domain-containing phosphotyrosine phosphatase 2 (Shp2) controls surface GluA1 protein in synaptic homeostasis.
    Authors: Zhang and Lu
    J Biol Chem  2017;292:15481
  14. A versatile optical tool for studying synaptic GABAA receptor trafficking.
    Authors: Lorenz-Guertin Et al.
    J Cell Sci  2017;130:3933
  15. Increased Activity of Src Homology 2 Domain Containing Phosphotyrosine Phosphatase 2 (Shp2) Regulates Activity-dependent AMPA Receptor Trafficking.
    Authors: Zhang Et al.
    J Biol Chem  2016;291:18856
  16. Diminished KCC2 confounds synapse specificity of LTP during senescence.
    Authors: Ferando Et al.
    Nat Neurosci  2016;19:1197
  17. Potentiation of Schaffer-Collateral CA1 Synaptic Transmission by eEF2K and p38 MAPK Mediated Mechanisms.
    Authors: Weng Et al.
    Front Cell Neurosci  2016;10:247
  18. Branch-specific dendritic Ca2+ spikes cause persistent synaptic plasticity.
    Authors: Cichon and Gan
    Nature  2015;520:180
  19. Activation of the habenula complex evokes autonomic physiological responses similar to those associated with emotional stress.
    Authors: Ootsuka and Mohammed
    J Virol  2015;3
  20. Activity-dependent differences in function between proximal and distal Schaffer collaterals.
    Authors: Owen and Grover
    J Neurophysiol  2015;113:3646
  21. In Vivo Voltage-Sensitive Dye Study of Lateral Spreading of Cortical Activity in Mouse Primary Visual Cortex Induced by a Current Impulse.
    Authors: Fehérvári Et al.
    PLoS One  2015;10:e0133853
  22. DA Promotes Motor Cortex Plasticity and Motor Skill Learning via PLC Activation.
    Authors: Rioult-Pedotti Et al.
    J Neurosci  2015;10:e0124986
  23. DA preferentially inhibits NMDA receptor-mediated EPSCs by acting on presynaptic D1 receptors in nucleus accumbens during postnatal development.
    Authors: Zhang Et al.
    PLoS One  2014;9:e86970
  24. Electrophysiological characterization of granule cells in the dentate gyrus immediately after birth.
    Authors: Pedroni Et al.
    Front Cell Neurosci  2014;8:44
  25. Synaptic plasticity in glutamatergic and GABAergic neurotransmission following chronic Mem. treatment in an in vitro model of limbic epileptogenesis.
    Authors: He and Bausch
    J Neurophysiol  2014;77:379
  26. Glycine induces bidirectional modifications in N-MthD.-aspartate receptor-mediated synaptic responses in hippocampal CA1 neurons.
    Authors: Zhang Et al.
    PLoS Pathog  2014;289:31200
  27. GABAergic influence on temporomandibular joint-responsive spinomedullary neurons depends on estrogen status.
    Authors: Tashiro Et al.
    Proc Natl Acad Sci U S A  2014;259:53
  28. The sphingolipid receptor S1PR2 is a receptor for Nogo-a repressing synaptic plasticity.
    Authors: Kempf Et al.
    PLoS Biol  2014;12:e1001763
  29. Role of inhibition in respiratory pattern generation.
    Authors: Janczewski Et al.
    J Neurosci  2013;33:5454
  30. The dorsomedial hypothalamus mediates stress-induced hyperalgesia and is the source of the pronociceptive peptide cholecystokinin in the rostral ventromedial medulla.
    Authors: Wagner Et al.
    Physiol Rep  2013;238:29
  31. Iberiotoxin-sensitive and -insensitive BK currents in Purkinje neuron somata.
    Authors: Benton Et al.
    J Neurophysiol  2013;109:2528
  32. Synaptic and extrasynaptic plasticity in glutamatergic circuits involving dentate granule cells following chronic N-MthD.-aspartate receptor inhibition.
    Authors: He Et al.
    Neuroscience  2013;109:1535
  33. Striatal DA transmission is subtly modified in human A53Tα-synuclein overexpressing mice.
    Authors: Platt Et al.
    PLoS One  2012;7:e36397
  34. Increased Kv1 channel expression may contribute to decreased sIPSC frequency following chronic inhibition of NR2B-containing NMDAR.
    Authors: He Et al.
    Neuropsychopharmacology  2012;37:1338
  35. Restoration of intracortical and thalamocortical circuits after transplantation of bone marrow mesenchymal stem cells into the ischemic brain of mice.
    Authors: Song Et al.
    Cell Transplant  2012;22:2001
  36. Inflammation-induced shift in spinal GABA(A) signaling is associated with a tyrosine kinase-dependent increase in GABA(A) current density in nociceptive afferents.
    Authors: Zhu Et al.
    J Neurophysiol  2012;108:2581
  37. Decreased afferent excitability contributes to synaptic depression during high-frequency stimulation in hippocampal area CA1.
    Authors: Kim Et al.
    J Neurophysiol  2012;108:1965
  38. D(2)-like DA receptors differentially regulate unitary IPSCs depending on presynaptic GABAergic neuron subtypes in rat nucleus accumbens shell.
    Authors: Kohnomi Et al.
    J Neurophysiol  2012;107:692
  39. Neuronal nitric oxide contributes to neuroplasticity-associated protein expression through cGMP, protein kinase G, and extracellular signal-regulated kinase.
    Authors: Gallo and Iadecola
    J Neurosci  2011;31:6947
  40. Activity-dependent ubiquitination of the AMPA receptor subunit GluA2.
    Authors: Lussier Et al.
    Pharmacol Res Perspect  2011;31:3077
  41. Differential expression and sensitivity of presynaptic and postsynaptic opioid receptors regulating hypothalamic proopiomelanocortin neurons.
    Authors: Pennock and Hentges
    J Neurosci  2011;31:281
  42. NE causes a biphasic change in mammalian pinealocye membrane potential: role of alpha1B-adrenoreceptors, phospholipase C, and Ca2+.
    Authors: Zemkova Et al.
    Endocrinology  2011;152:3842
  43. Control of cerebellar long-term potentiation by P-Rex-family guanine-nucleotide exchange factors and phosphoinositide 3-kinase.
    Authors: Jackson Et al.
    PLoS One  2010;5:e11962
  44. Activation of NR2A receptors induces ischemic tolerance through CREB signaling.
    Authors: Terasaki Et al.
    J Cereb Blood Flow Metab  2010;30:1441
  45. Activation of muscarinic acetylcholine receptors induces a nitric oxide-dependent long-term depression in rat medial prefrontal cortex.
    Authors: Huang and Hsu
    Cereb Cortex  2010;20:982
  46. KCC2 expression promotes the termination of cortical interneuron migration in a voltage-sensitive calcium-dependent manner.
    Authors: Bortone and Polleux
    Neuron  2009;62:53
  47. Mutation of the protein kinase C site in borna disease virus phosphoprotein abrogates viral interference with neuronal signaling and restores normal synaptic activity.
    Authors: Prat Et al.
    Neuroscience  2009;5:e1000425
  48. An activity-regulated microRNA controls dendritic plasticity by down-regulating p250GAP.
    Authors: Wayman Et al.
    PLoS One  2008;105:9093
  49. Borna disease virus infection impairs synaptic plasticity.
    Authors: Volmer Et al.
    J Biol Chem  2007;81:8833
  50. Glutamate receptor expression and chronic glutamate toxicity in rat motor cortex.
    Authors: Young Et al.
    Neurobiol Dis  2007;26:78
  51. HCN2 and HCN1 channels govern the regularity of autonomous pacemaking and synaptic resetting in globus pallidus neurons.
    Authors: Chan Et al.
    J Neurosci  2004;24:9921

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