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B7561

Sigma-Aldrich

1(S),9(R)-(−)-Bicuculline methbromide

≥98% (HPLC), solid

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Synonym(s):
(5S)-5-[(6R)-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 bromide (1:1)
Empirical Formula (Hill Notation):
C21H20BrNO6
CAS Number:
Molecular Weight:
462.29
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

H2O: >10 mg/mL

storage temp.

2-8°C

SMILES string

[Br-].C[N+]1(C)CCc2cc3OCOc3cc2[C@H]1[C@@H]4OC(=O)c5c6OCOc6ccc45

InChI

1S/C21H20NO6.BrH/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

InChI key

BWXCECYGGMGBHD-GRTNUQQKSA-M

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Application

1(S),9(R)-(-)-Bicuculline methbromide has been used:
  • as a γ-aminobutyric acid (GABAA) receptor A antagonist: in cortical neuron culture
  • in artificial cerebrospinal fluid (ACSF) formature dentate granule neurons
  • in hypothalamic explant cultures

Biochem/physiol Actions

1(S),9(R)-(−)-Bicuculline methbromide is a GABAA receptor antagonist, which blocks Ca2+-activated potassium (SK) channels. It is the water-soluble derivative of (+)-bicuculline.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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Skull and crossbonesEnvironment

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Danger

Hazard Classifications

Acute Tox. 1 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Aquatic Acute 1 - Aquatic Chronic 1

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

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Amar Sahay et al.
Nature, 472(7344), 466-470 (2011-04-05)
Adult hippocampal neurogenesis is a unique form of neural circuit plasticity that results in the generation of new neurons in the dentate gyrus throughout life. Neurons that arise in adults (adult-born neurons) show heightened synaptic plasticity during their maturation and
Delphine Franssen et al.
Endocrinology, 157(5), 1740-1750 (2016-03-08)
Rat sexual maturation is preceded by a reduction of the interpulse interval (IPI) of GnRH neurosecretion. This work aims at studying disruption of that neuroendocrine event in females after early exposure to a very low dose of bisphenol A (BPA)
K Seo et al.
Brain research, 892(1), 198-202 (2001-02-15)
The effect of intrathecal administration of the GABA(A) receptor antagonist bicuculline methylbromide on jaw muscle electromyographic (EMG) activity evoked by mustard oil injection into the rat temporomandibular joint was studied. Bicuculline given prior to mustard oil augmented the EMG activity
Xiaofen Zhong et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 32(37), 12841-12847 (2012-09-14)
MeCP2 (methyl CpG binding protein 2) is a key player in recognizing methylated DNA and interpreting the epigenetic information encoded in different DNA methylation patterns. The functional significance of MeCP2 to the mammalian nervous system is highlighted by the discovery
M A Castro-Alamancos
The Journal of neuroscience : the official journal of the Society for Neuroscience, 20(24), 9195-9206 (2000-01-11)
During disinhibition, the neocortex generates synchronous activities. Block of GABA(A) receptors in neocortex transforms cortical slow-wave oscillations into large-amplitude approximately 1 Hz discharges consisting of a negative spike or multiple negative spikes riding on a positive wave. Further block of

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