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14343

1(S),9(R)-(−)-Bicuculline methiodide

Name: 1(<I>S</I>),9(<I>R</I>)-(&#8722;)-Bicuculline methiodide
Brand: SIGMA

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

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

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

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Product Name

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

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

Related Categories

Bioactive Small Molecules

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Bicuculline block of small-conductance calcium-activated potassium channels

Khawaled R, et al.

Pfluegers Archiv, 438(3), 314-321 (1999)

GABA(A) receptor blockade enhances memory consolidation by increasing hippocampal BDNF levels.

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)

Poisons of Plant Origin (2013)

The effects of electrical microstimulation on cortical signal propagation.

Nikos K Logothetis et al.

Nature neuroscience, 13(10), 1283-1291 (2010-09-08)

Electrical stimulation has been used in animals and humans to study potential causal links between neural activity and specific cognitive functions. Recently, it has found increasing use in electrotherapy and neural prostheses. However, the manner in which electrical stimulation-elicited signals

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Global Trade Item Number

SKU	GTIN
H7021-100MG	04061832862552
14343-50MG	04061838734853
14343-10MG	04061838734846

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