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B7686

Sigma-Aldrich

1(S),9(R)-(−)-Bicuculline methchloride

≥97% (HPLC), powder

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About This Item

Linear Formula:
C21H20NO6Cl
CAS Number:
38641-83-7
Molecular Weight:
417.84
MDL number:
MFCD00055233
UNSPSC Code:
12352200
PubChem Substance ID:
329773300
NACRES:
NA.77

Quality Level

100

assay

≥97% (HPLC)

form

powder

solubility

H2O: >10 mg/mL

storage temp.

2-8°C

SMILES string

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

InChI

1S/C21H20NO6.ClH/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

RLJKFAMYSYWMND-GRTNUQQKSA-M

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Biochem/physiol Actions

1(S),9(R)-(−)-Bicuculline methchloride is a GABAA receptor antagonist, which blocks Ca2+-activated potassium (SK) channels.

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.
This compound is featured on the GABAA Receptors and Potassium Channels pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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M Müller et al.
Proceedings of the National Academy of Sciences of the United States of America, 90(1), 257-261 (1993-01-01)
The morphological and functional consequences of epileptic activity were investigated by applying the convulsants bicuculline and/or picrotoxin to mature rat hippocampal slice cultures. After 3 days, some cells in all hippocampal subfields showed signs of degeneration, including swollen somata, vacuolation
H Qian et al.
Nature, 361(6408), 162-164 (1993-01-14)
gamma-Aminobutyric acid (GABA) is the main inhibitory neurotransmitter in the central nervous system. Two classes of GABA receptors (GABAA and GABAB) have been identified. GABAA receptors are ligand-gated chloride channels that are competitively antagonized by bicuculline, noncompetitively blocked by picrotoxin
O Paulsen et al.
The Journal of physiology, 496 ( Pt 3), 759-772 (1996-11-01)
1. Spontaneous non-NMDA glutamate receptor-mediated EPSCs were recorded with the whole-cell patch-clamp technique from twenty-six neurones in the dorsal lateral geniculate nucleus in thalamic slices from guinea-pig. 2. Amplitude distributions of the EPSCs were skewed towards larger values. The skewness
L C Yu et al.
The International journal of neuroscience, 54(3-4), 245-251 (1990-10-01)
This study explored the possibility of a relay at habenula for the descending neural pathway of antinociception. The latency of the escape response elicited by radiant heat on the snout of the rabbit was taken as index of nociception. (1)
Jinny J Yoon et al.
Epilepsy research, 92(2-3), 153-162 (2010-09-21)
Epileptic seizures typically result in delayed neuronal loss secondary to the initial damage and an up-regulation in connexin43 (Cx43). This study investigated the role of Cx43 gap junctions in lesion spread and cell loss following epileptiform activity. Epileptiform injury in
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