(-)-Bicuculline methiodide - CAS 40709-69-1
Category: Inhibitor
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Molecular Formula:
C21H20INO6
Molecular Weight:
509.3
COA:
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Targets:
GABA Receptor
Description:
(-)-Bicuculline methiodide is the methiodide salt of (+)-bicuculline, which is a potent antagonist of GABAA receptors.
Brife Description:
GABAA receptor antagonist
Purity:
≥99% by HPLC
Synonyms:
[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
MSDS:
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InChIKey:
HKJKCPKPSSVUHY-GRTNUQQKSA-M
InChI:
InChI=1S/C21H20NO6.HI/c1-22(2)6-5-11-7-15-16(26-9-25-15)8-13(11)18(22)19-12-3-4-14-20(27-10-24-14)17(12)21(23)28-19;/h3-4,7-8,18-19H,5-6,9-10H2,1-2H3;1H/q+1;/p-1/t18-,19+;/m0./s1
Canonical SMILES:
C[N+]1(CCC2=CC3=C(C=C2C1C4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3)C.[I-]
1.Rebound bursts in GABAergic neurons of the thalamic reticular nucleus in postnatal mice.
Wang X;Yu G;Hou X;Zhou J;Yang B;Zhang L Physiol Res. 2010;59(2):273-80. Epub 2009 Jun 19.
Whole cell patch-clamp recordings from GABAergic cells of thalamic reticular nucleus (RTN) in thalamocortical slices made from postnatal day 6 (P6) to 10 (P10) were used to investigate the pattern of rebound bursts (RBs) triggered by an injection of hyperpolarizing current into RTN cells. The number of RBs in the RTN and the overlying Na(+)/K(+) spikes changed in an age-dependent manner. The generation of RBs depended largely on the amplitude of the after-hyperpolarizations (AHPs). RB patterns in response to hyperpolarizing current injection into relay cells were markedly different from RB patterns in RTN cells with an after-depolarization. GABA(A) receptor antagonist bicuculline methiodide (BMI) changed burst firing patterns, increasing the duration of RB and decreasing the amplitude of AHP in RTN cells. Furthermore, local puffs of NMDA in the presence of BMI induced RBs. K(+) channel blocker 4-aminopyridine partially mimicked the effect of BMI on AHPs. The shapes of RBs were altered by a selective CaMKII inhibitor KN-62, but not by an inactive analog KN-04.
2.Bicuculline increases Ca2+ transients in rat cerebellar granule cells through non-GABA(A) receptor associated mechanisms.
Mestdagh N;Wülfert E Neurosci Lett. 1999 Apr 16;265(2):95-8.
The effects of bicuculline methiodide (bicuculline) and gabazine, two GABA(A) antagonists, on cytosolic calcium increases (Ca2+ transients) in rat cerebellar granule cells were examined using Fluo-3-spectrofluorometry. Bicuculline (25 microM) markedly potentiated Ca2+ transients caused by KCl (25 mM) and by A23187 (4 microM) whereas gabazine (25 microM) had no effect. Calcium increases caused by glutamate (2 microM), N-methyl-D-aspartic acid (200 microM), trans-1-amino-cyclopentane-1,3 dicarboxylate (200 microM), thapsigargin (1 microM) or caffeine (5 mM) were not altered by bicuculline. Thapsigargin, which depletes intracellular Ca2+ stores, had no effect on either KCl- or A23187-induced Ca2+ transients, but completely blocked bicuculline-induced potentiation of Ca2+ increases. Our data suggest that bicuculline triggers calcium release when calcium entry is evoked by KCl or A23187 and that this effect is not mediated via GABA(A) receptor blockade.
3.Gamma-aminobutyric acid enhancement of potassium-stimulated release of [3H]norepinephrine by multiple mechanisms in rat cortical slices.
Peoples RW;Giridhar J;Isom GE Biochem Pharmacol. 1991 Jan 1;41(1):119-23.
Gamma-Aminobutyric acid (GABA) and GABAA agonists enhance stimulated release of [3H]norepinephrine [( 3H]NA) in several regions of the rat brain. In this study, the mechanisms by which GABA and GABAergic agonists augment potassium-stimulated release of [3H]NA from rat frontal cortical slices were examined. GABA enhanced potassium-stimulated [3H]NA release, but did not alter release of [3H]NA evoked by the calcium ionophore A23187, 10(-5) M, either in the presence or the absence of extracellular calcium. The effect of GABA on potassium-stimulated [3H]NA release was apparently reduced by the GABAA antagonist bicuculline methiodide, 10(-4) M, and by the selective inhibitor of GABA uptake SKF 89976A, 10(-5) M, but was abolished only when bicuculline methiodide and SKF 89976A were present in combination. The GABAA agonist muscimol enhanced potassium-stimulated release of [3H]NA in a manner similar to GABA. In addition, nipecotic acid, a substrate for GABA uptake, enhanced potassium-stimulated [3H]NA release. Thus, GABA appears to enhance potassium-stimulated [3H]NA release by acting upon both GABA uptake and GABAA receptors. The GABAA receptors involved in this effect may be a subtype of GABAA receptors since they are not modulated by benzodiazepines.
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CAS 40709-69-1 (-)-Bicuculline methiodide

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