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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
Pricing and availability is not currently available.

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

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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
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
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
G Maksay et al.
Journal of neurochemistry, 61(6), 2081-2088 (1993-12-01)
The kinetics of t-[3H]butylbicycloorthobenzoate (TBOB) binding to the convulsant sites of the gamma-aminobutyric acidA (GABAA) receptor-ionophore complex were examined in synaptosomal membrane preparations of rat brain. On and off rates of TBOB binding were accelerated by 1 microM GABA and
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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