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Merck

B7686

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

≥97% (HPLC), GABAA receptor antagonist, powder

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About This Item

Linear Formula:
C21H20NO6Cl
CAS Number:
38641-83-7
Molecular Weight:
417.84
UNSPSC Code:
12352200
PubChem Substance ID:
329773300
NACRES:
NA.77
MDL number:
MFCD00055233
Assay:
≥97% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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Product Name

1(S),9(R)-(−)-Bicuculline methchloride, ≥97% (HPLC), powder

SMILES string

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

InChI key

RLJKFAMYSYWMND-GRTNUQQKSA-M

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

assay

≥97% (HPLC)

form

powder

solubility

H2O: >10 mg/mL

storage temp.

2-8°C

Quality Level

100

Related Categories

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000187043
0000186342
0000186342
0000187043
0000136568

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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
C M van Rijn et al.
Journal of receptor and signal transduction research, 15(6), 787-800 (1995-07-01)
Interactions of GABA, bicuculline methochloride and diazepam with [3H]TBOB binding to rat brain membranes were evaluated in vitro. GABA displaced [3H]TBOB binding with and IC50 of 4 microM and a slope factor near unity. The competitive GABA antagonist bicuculline methochloride
K Gottmann et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 17(8), 2766-2774 (1997-04-15)
Subunit composition of subsynaptic transmitter receptors is controlled presynaptically in the developing neuromuscular junction. To investigate presynaptic regulation of NMDA receptor subunit composition in the CNS, we co-cultured different types of hippocampal explants with dissociated target neurons. Postsynaptic NMDA receptors
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
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
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