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Merck
CN

14343

1(S),9(R)-(−)-Bicuculline methiodide

≥95.0% (HPCE), GABAA receptor antagonist, powder

别名:

(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 iodide

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关于此项目

经验公式（希尔记法）:
C21H20INO6
化学文摘社编号:
40709-69-1
分子量:
509.29
Beilstein:
5419649
MDL编号:
MFCD00078966
UNSPSC代码:
12352200
PubChem化学物质编号:
329750456
NACRES:
NA.77

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产品名称

1(S),9(R)-(−)-Bicuculline methiodide, ≥95.0% (HPCE)

质量水平

100

方案

≥95.0% (HPCE)

表单

powder

旋光性

[α]/D -117±7°, c = 1 in chloroform

溶解性

H2O: 10 mg/mL, almost clear, greenish-yellow

储存温度

2-8°C

SMILES字符串

[I-].[H][C@]1(OC(=O)c2c3OCOc3ccc12)[C@]4([H])c5cc6OCOc6cc5CC[N+]4(C)C

InChI

1S/C21H20NO6.HI/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

HKJKCPKPSSVUHY-GRTNUQQKSA-M

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相关类别

一般描述

Bicuculline is a phthalide isoquinoline alkaloid, which is extracted from Dicentra cucullaria. It acts as an acetylcholinesterase inhibitor. Bicuculline inhibits slow afterhyperpolarization (AHP).

应用

1(S),9(R)-(-)-Bicuculline methiodide has been used as a gamma-aminobutyric acid (GABA) antagonist to block inhibition in the semicoronal slices. It has also been used for the preparation of organotypic hippocampal slice cultures (OHSCs).

生化/生理作用

(-)-Bicuculline methiodide is a GABAA receptor antagonist, which acts as a competitive inhibitor of GABA ligand binding to the receptor.

特点和优势

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.

制备说明

prepared from (+)-bicuculline

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
BCBV5862
BCBN1844V
BCBF8612V
1392960V
1402092V

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Bicuculline block of small-conductance calcium-activated potassium channels
Khawaled R, et al.
Pfluegers Archiv, 438(3), 314-321 (1999)
Electrophysiological characterization of networks and single cells in the hippocampal region of a transgenic rat model of Alzheimer?s disease
Heggland I, et al.
eNeuro, 6(1) (2019)
Dong Hyun Kim et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 37(2), 422-433 (2011-09-09)
Memory consolidation is the process by which acquired information is converted to something concrete to be retrieved later. Here we examined a potential role for brain-derived neurotrophic factor (BDNF) in mediating the enhanced memory consolidation induced by the GABA(A) receptor
Shoko Iida et al.
Biochemical and biophysical research communications, 501(1), 152-157 (2018-05-04)
The balance between glutamate-mediated excitation and GABA-mediated inhibition is critical to cortical functioning. However, the contribution of network structure consisting of the both neurons to cortical functioning has not been elucidated. We aimed to evaluate the relationship between the network
Poisons of Plant Origin (2013)
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