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Merck

14343

1(S),9(R)-(−)-Bicuculline methiodide

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

동의어(들):

(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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제품정보 (DICE 배송 시 비용 별도)

실험식(Hill 표기법):
C21H20INO6
CAS 번호:
40709-69-1
Molecular Weight:
509.29
NACRES:
NA.77
PubChem Substance ID:
329750456
UNSPSC Code:
12352200
MDL number:
MFCD00078966
Beilstein/REAXYS Number:
5419649
Assay:
≥95.0% (HPCE)
Form:
powder
Quality level:
100

주요 문서

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제품 이름

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

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

SMILES string

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

InChI key

HKJKCPKPSSVUHY-GRTNUQQKSA-M

assay

≥95.0% (HPCE)

form

powder

optical activity

[α]/D -117±7°, c = 1 in chloroform

solubility

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

storage temp.

2-8°C

Quality Level

100

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관련 카테고리

Application

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).

Biochem/physiol Actions

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

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.

General description

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

Preparation Note

prepared from (+)-bicuculline

저장 등급

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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시험 성적서(COA)

Lot/Batch Number
BCBV5862
BCBN1844V
BCBF8612V
1392960V
1402092V

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COA 검색

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문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문

Bicuculline block of small-conductance calcium-activated potassium channels
Khawaled R, et al.
Pfluegers Archiv, 438(3), 314-321 (1999)
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
Poisons of Plant Origin (2013)
Charles Capaday et al.
The Journal of physiology, 589(Pt 10), 2515-2528 (2011-04-14)
Motor cortical points are linked by intrinsic horizontal connections having a recurrent network topology. However, it is not known whether neural activity can propagate over the area covered by these intrinsic connections and whether there are spatial anisotropies of synaptic
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)
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