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14343

Sigma-Aldrich

1(S),9(R)-(−)-Bicuculline methiodide

≥95.0% (HPCE)

Synonym(s):

(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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About This Item

Empirical Formula (Hill Notation):
C21H20INO6
CAS Number:
40709-69-1
Molecular Weight:
509.29
Beilstein:
5419649
MDL number:
MFCD00078966
UNSPSC Code:
12352200
PubChem Substance ID:
329750456
NACRES:
NA.77

Quality Level

100

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

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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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
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)
Bicuculline block of small-conductance calcium-activated potassium channels
Khawaled R, et al.
Pfluegers Archiv, 438(3), 314-321 (1999)
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