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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크기 선택
보기 변경
제품정보 (DICE 배송 시 비용 별도)
실험식(Hill 표기법):
C21H20INO6
CAS 번호:
Molecular Weight:
509.29
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Beilstein/REAXYS Number:
5419649
제품 이름
1(S),9(R)-(−)-Bicuculline methiodide, ≥95.0% (HPCE)
Quality Level
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
SMILES string
[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
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).
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.
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)
문서
신경과학을 위한 생체 활성 저분자
DISCOVER Bioactive Small Molecules for Neuroscience
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
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