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B7561

Sigma-Aldrich

1(S),9(R)-(−)-Bicuculline methbromide

≥98% (HPLC), solid

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)

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About This Item

Empirical Formula (Hill Notation):
C21H20BrNO6
CAS Number:
66016-70-4
Molecular Weight:
462.29
MDL number:
MFCD00055149
UNSPSC Code:
12352200
PubChem Substance ID:
329773298
NACRES:
NA.77

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.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H300,H311 + H331,H410

Hazard Classifications

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

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Doris P Molina et al.
Neurobiology of aging, 33(9), 1938-1949 (2011-10-22)
Alterations in the alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate receptor (AMPA-R) and N-methyl-D-aspartate receptor (NMDA-R) have been documented in aged animals and may contribute to changes in hippocampal-dependent memory. Growth hormone (GH) regulates AMPA-R and NMDA-R-dependent excitatory transmission and decreases with age. Chronic GH treatment
M Grunnet et al.
Neuropharmacology, 40(7), 879-887 (2001-05-30)
Small-conductance, calcium-activated K+ channels (SK channels) are voltage-insensitive channels that have been identified molecularly within the last few years. As SK channels play a fundamental role in most excitable cells and participate in afterhyperpolarization (AHP) and spike-frequency adaptation, pharmacological modulation
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
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