(+)-Bicuculline

Pricing Availability Delivery Time Qty
Cat.No. 0130 - (+)-Bicuculline | C20H17NO6 | CAS No. 485-49-4
Description: Potent GABAA antagonist
Chemical Name: [R-(R*,S*)]-6-(5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)furo[3,4-e]-1,3-benzodioxol-8(6H)-one
Purity: ≥99% (HPLC)
Datasheet
Citations (67)
Literature

Biological Activity

Classical GABAA antagonist. Methoiodide salt (Cat. No. 2503), Methobromide salt (Cat. No. 0109) and Methochloride salt (Cat. No. 0131) also available.

Technical Data

M. Wt 367.36
Formula C20H17NO6
Storage Store at +4°C
Purity ≥99% (HPLC)
CAS Number 485-49-4
PubChem ID 10237
InChI Key IYGYMKDQCDOMRE-ZWKOTPCHSA-N
Smiles [H][C@](C(C=CC6=C5OCO6)=C5C(O4)=O)4[C@]2([H])C1=CC3=C(OCO3)C=C1CCN2C

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 36.74 100

Preparing Stock Solutions

The following data is based on the product molecular weight 367.36. 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 2.72 mL 13.61 mL 27.22 mL
5 mM 0.54 mL 2.72 mL 5.44 mL
10 mM 0.27 mL 1.36 mL 2.72 mL
50 mM 0.05 mL 0.27 mL 0.54 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 products' biological activity.

Curtis et al (1970) GABA, bicuculline and central inhibition. Nature 226 1222 PMID: 4393081

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

Piredda et al (1985) Intracerebral site of convulsant action of bicuculline. Life Sci. 36 1295 PMID: 3982215

Sieghart et al (1989) Multiplicity of GABAA-benzodiazepine receptors. TiPS 10 407 PMID: 2559519

Merck Index 12 1250 PMID:


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Keywords: Potent GABAA antagonists Receptors GABAA Receptors

67 Citations for (+)-Bicuculline

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

Dinamarca et al (2016) Ring finger protein 10 is a novel synaptonuclear messenger encoding activation of NMDA receptors in hippocampus. Elife 5 PMID: 26977767

Imlach et al (2016) Glycinergic dysfunction in a subpopulation of dorsal horn interneurons in a rat model of neuropathic pain Scientific Reports 6 37104  PMID: 27841371

Dubal et al (2015) Life extension factor klotho prevents mortality and enhances cognition in hAPP transgenic mice. J Neurosci 35 2358 PMID: 25673831

Ciani et al (2015) Wnt signalling tunes neurotransmitter release by directly targeting Synaptotagmin-1. Nat Commun 6 8302 PMID: 26400647

Hengen et al (2015) Daily isoflurane exposure increases barbiturate insensitivity in medullary respiratory and cortical neurons via expression of η-subunit containing GABA ARs. PLoS One 10 e0119351 PMID: 25748028

Wu et al (2015) Soluble epoxide hydrolase inhibitor enhances synaptic neurotransmission and plasticity in mouse prefrontal cortex. J Biomed Sci 22 94 PMID: 26494028

Morini et al (2015) Subventricular zone neural progenitors reverse TNF-α effects in cortical neurons. Stem Cell Res Ther 6 166 PMID: 26345473

Pappas et al (2015) Forebrain deletion of the dystonia protein torsinA causes dystonic-like movements and loss of striatal cholinergic neurons. Elife 4 e08352 PMID: 26052670

Telese et al (2015) LRP8-Reelin-Regulated Neuronal Enhancer Signature Underlying Learning and Memory Formation. Neuron 86 696 PMID: 25892301

Campbell et al (2015) Functional changes in glutamate transporters and astrocyte biophysical properties in a rodent model of focal cortical dysplasia. Front Cell Neurosci 8 425 PMID: 25565960

Curcio et al (2015) Brain ischemia downregulates the neuroprotective GDNF-Ret signaling by a calpain-dependent mechanism in cultured hippocampal neurons. Cell Death Dis 6 e1645 PMID: 25675305

Huckstepp et al (2015) Role of parafacial nuclei in control of breathing in adult rats. J Neurosci 35 1052 PMID: 25609622

Puranam et al (2015) Disruption of Fgf13 causes synaptic excitatory-inhibitory imbalance and genetic epilepsy and febrile seizures plus. J Neurosci 35 8866 PMID: 26063919

Baquero et al (2015) Developmental changes in synaptic distribution in arcuate nucleus neurons. J Neurosci 35 8558 PMID: 26041922

John et al (2015) Functional α7 nicotinic receptors are expressed on immature granule cells of the postnatal dentate gyrus. Brain Res 1601 15 PMID: 25553616

Lee et al (2015) N-methyl-D-aspartate receptors mediate activity-dependent down-regulation of potassium channel genes during the expression of homeostatic intrinsic plasticity. Mol Brain 8 4 PMID: 25599691

Quintana et al (2015) Acid-sensing ion channel 1a drives AMPA receptor plasticity following ischaemia and acidosis in hippocampal CA1 neurons. J Physiol 593 4373 PMID: 26174503

Zimmermann et al (2015) Co-release of glutamate and GABA from single vesicles in GABAergic neurons exogenously expressing VGLUT3. Front Synaptic Neurosci 7 16 PMID: 26441632

Ding et al (2015) The reinforcing effects of ethanol within the nucleus accumbens shell involve activation of local GABA and serotonin receptors. J Psychopharmacol 29 725 PMID: 25922425

Kangarlu-Haghighi et al (2015) The effect of BLA GABA(A) receptors in anxiolytic-like effect and aversive memory deficit induced by ACPA. EXCLI J 14 613 PMID: 26648818

Robinson et al (2015) Tissue plasminogen activator inhibits NMDA-receptor-mediated increases in calcium levels in cultured hippocampal neurons. Front Cell Neurosci 9 404 PMID: 26500501

Bernard and Zhang (2015) MARK/Par1 Kinase Is Activated Downstream of NMDA Receptors through a PKA-Dependent Mechanism. PLoS One 10 e0124816 PMID: 25932647

Curtin and Preuss (2015) Glycine and GABAA receptors mediate tonic and phasic inhibitory processes that contribute to prepulse inhibition in the goldfish startle network. Front Neural Circuits 9 12 PMID: 25852486

Lee et al (2014) Long-term depression-inducing stimuli promote cleavage of the synaptic adhesion molecule NGL-3 through NMDA receptors, matrix metalloproteinases and presenilin/γ-secretase. Philos Trans R Soc Lond B Biol Sci 369 20130158 PMID: 24298159

Bemben et al (2014) CaMKII phosphorylation of neuroligin-1 regulates excitatory synapses. Nat Neurosci 17 56 PMID: 24336150

Weston et al (2014) Loss of mTOR repressors Tsc1 or Pten has divergent effects on excitatory and inhibitory synaptic transmission in single hippocampal neuron cultures. Front Mol Neurosci 7 1 PMID: 24574959

Suzuki et al (2014) Imaging intraorganellar Ca2+ at subcellular resolution using CEPIA. Nat Commun 5 4153 PMID: 24923787

Gaffaney et al (2014) Mutations that disrupt Ca2+-binding activity endow Doc2β with novel functional properties during synaptic transmission. Mol Biol Cell 25 481 PMID: 24356452

Oostland et al (2014) Distinct temporal expression of 5-HT(1A) and 5-HT(2A) receptors on cerebellar granule cells in mice. Cerebellum 13 491 PMID: 24788088

Chen et al (2014) Activation of mGluR2/3 underlies the effects of N-acetylcystein on amygdala-associated autism-like phenotypes in a valproate-induced rat model of autism. Front Behav Neurosci 8 219 PMID: 24987341

Velmans et al (2013) Plasticity-related gene 3 promotes neurite shaft protrusion. BMC Neurosci 14 36 PMID: 23506325

Korb et al (2013) Arc in the nucleus regulates PML-dependent GluA1 transcription and homeostatic plasticity. Nat Neurosci 16 874 PMID: 23749147

Zemoura et al (2013) Endoplasmic reticulum-associated degradation controls cell surface expression of γ-aminobutyric acid, type B receptors. J Biol Chem 288 34897 PMID: 24114844

Berlinguer-Palmini et al (2013) GPR35 activation reduces Ca2+ transients and contributes to the kynurenic acid-dependent reduction of synaptic activity at CA3-CA1 synapses. PLoS One 8 e82180 PMID: 24312407

Hur and Park (2013) Long-term potentiation of excitatory synaptic strength in spinothalamic tract neurons of the rat spinal cord. Korean J Physiol Pharmacol 17 553 PMID: 24381506

Medrihan et al (2013) Synapsin II desynchronizes neurotransmitter release at inhibitory synapses by interacting with presynaptic calcium channels. Nat Commun 4 1512 PMID: 23443540

Chen et al (2013) The Munc13 proteins differentially regulate readily releasable pool dynamics and calcium-dependent recovery at a central synapse. J Neurosci 33 8336 PMID: 23658173

Hou and Yu (2013) Activity-regulated somatostatin expression reduces dendritic spine density and lowers excitatory synaptic transmission via postsynaptic somatostatin receptor 4. J Biol Chem 288 2501 PMID: 23233668

Gao and Derbenev (2013) Synaptic and extrasynaptic transmission of kidney-related neurons in the rostral ventrolateral medulla. J Neurophysiol 110 2637 PMID: 24027107

Daftary et al (2012) Essential role of brain-derived neurotrophic factor in the regulation of serotonin transmission in the basolateral amygdala. Neuroscience 224 125 PMID: 22917617

Kaufman et al (2012) Opposing roles of synaptic and extrasynaptic NMDA receptor signaling in cocultured striatal and cortical neurons. J Neurosci 32 3992 PMID: 22442066

Yao et al (2012) Uncoupling the roles of synaptotagmin I during endo- and exocytosis of synaptic vesicles. Nat Neurosci 15 243 PMID: 22197832

Yamamoto et al (2012) Raf kinase inhibitory protein is required for cerebellar long-term synaptic depression by mediating PKC-dependent MAPK activation. J Neurosci 32 14254 PMID: 23055494

Dagostin et al (2012) Increased bursting glutamatergic neurotransmission in an auditory forebrain area of the zebra finch (Taenopygia guttata) induced by auditory stimulation. J Comp Physiol A Neuroethol Sens Neural Behav Phys 198 705 PMID: 22752655

Zhu et al (2011) Basolateral amygdala inactivation impairs learning-induced long-term potentiation in the cerebellar cortex. PLoS One 6 e16673 PMID: 21304962

Uschakov et al (2011) Sleep-deprivation regulates α-2 adrenergic responses of rat hypocretin/orexin neurons. PLoS One 6 e16672 PMID: 21347440

Mou et al (2011) Rapid brain-derived neurotrophic factor-dependent sequestration of amygdala and hippocampal GABA(A) receptors via different tyrosine receptor kinase B-mediated phosphorylation pathways. Neuroscience 176 72 PMID: 21195749

Porcher et al (2011) Positive feedback regulation between γ-aminobutyric acid type A (GABA(A)) receptor signaling and brain-derived neurotrophic factor (BDNF) release in developing neurons. J Biol Chem 286 21667 PMID: 21474450

Smejkalova and Woolley (2010) Estradiol acutely potentiates hippocampal excitatory synaptic transmission through a presynaptic mechanism. J Neurosci 30 16137 PMID: 21123560

Mah et al (2010) Selected SALM (synaptic adhesion-like molecule) family proteins regulate synapse formation. J Neurosci 30 5559 PMID: 20410109

Acuna-Goycolea et al (2010) Cannabinoids excite circadian clock neurons. J Neurosci 30 10061 PMID: 20668190

Yeh et al (2010) SV2 mediates entry of tetanus neurotoxin into central neurons. PLoS Pathog 6 e1001207 PMID: 21124874

Thyagarajan and Ting (2010) Imaging activity-dependent regulation of neurexin-neuroligin interactions using trans-synaptic enzymatic biotinylation. Cell 143 456 PMID: 20933261

Lin et al (2009) Characterization of engineered channelrhodopsin variants with improved properties and kinetics. Biophys J 96 1803 PMID: 19254539

Yeo et al (2009) Novel repression of Kcc2 transcription by REST-RE-1 controls developmental switch in neuronal chloride. J Neurosci 29 14652 PMID: 19923298

Kuroyanagi et al (2009) Postsynaptic glutamate receptor δ family contributes to presynaptic terminal differentiation and establishment of synaptic transmission. Proc Natl Acad Sci U S A 106 4912 PMID: 19258455

Young and Neher (2009) Synaptotagmin has an essential function in synaptic vesicle positioning for synchronous release in addition to its role as a calcium sensor. Neuron 63 482 PMID: 19709630

Andäng et al (2008) Histone H2AX-dependent GABA(A) receptor regulation of stem cell proliferation. Nature 451 460 PMID: 18185516

Hong et al (2008) Glutamatergic transmission is sustained at a later period of development of medial nucleus of the trapezoid body-lateral superior olive synapses in circling mice. J Neurosci 28 13003 PMID: 19036993

Soriano et al (2008) Specific targeting of pro-death NMDA receptor signals with differing reliance on the NR2B PDZ ligand. J Neurosci 28 10696 PMID: 18923045

Riccio et al (2006) A nitric oxide signaling pathway controls CREB-mediated gene expression in neurons. Mol Cell 21 283 PMID: 16427017

Surges et al (2006) Regulated expression of HCN channels and cAMP levels shape the properties of the h current in developing rat hippocampus. Eur J Neurosci 24 94 PMID: 16882011

Berghuis et al (2005) Endocannabinoids regulate interneuron migration and morphogenesis by transactivating the TrkB receptor. Proc Natl Acad Sci U S A 102 19115 PMID: 16357196

Alldred et al (2005) Distinct γ2 subunit domains mediate clustering and synaptic function of postsynaptic GABAA receptors and gephyrin. J Neurosci 25 594 PMID: 15659595

Lenz and Avruch (2005) Glutamatergic regulation of the p70S6 kinase in primary mouse neurons. J Biol Chem 280 38121 PMID: 16183639

Ying and Goldstein (2005) Propofol suppresses synaptic responsiveness of somatosensory relay neurons to excitatory input by potentiating GABA(A) receptor chloride channels. Mol Pain 1 2 PMID: 15813991

Huang et al (2004) Astrocyte glutamate transporters regulate metabotropic glutamate receptor-mediated excitation of hippocampal interneurons. J Neurosci 24 4551 PMID: 15140926


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