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14343

1(S),9(R)-(−)-Bicuculline methiodide

≥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

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)

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Certificates of Analysis (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)
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
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