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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 Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

B7686-125MG:
B7686-IP:
B7686-BULK:
B7686-25MG:
B7686-VAR:

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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B Pfleger et al.
Experimental brain research, 104(1), 81-88 (1995-01-01)
The influence of GABAA receptors on orientation selectivity of cat complex cells was tested by iontophoresis of the GABAA receptor blockers bicuculline and N-methyl-bicuculline while stimulating with drifting sinusoidal gratings. Reduction of orientation tuning was markedly less than reported in
Y Katz et al.
Brain research, 646(2), 235-241 (1994-05-23)
We examined the interactions of D,L-laudanosine, a potentially epileptogenic metabolite of the neuromuscular relaxant atracurium besylate, with gamma-aminobutyric acid (GABA) and opioid binding sites, all of which have been implicated in seizure activity. Laudanosine was almost ineffective at [3H]muscimol binding
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
Bryan Cruz et al.
Journal of neurochemistry, 156(2), 200-211 (2020-06-21)
This study examined whether insulin modulates the neurochemical effects of nicotine in the mesolimbic pathway of diabetic rats. The rats received vehicle or streptozotocin (STZ) to induce hypoinsulinemia. A subset of STZ-treated rats was implanted with insulin pellets that rapidly
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
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