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14343

Sigma-Aldrich

1(S),9(R)-(−)-Bicuculline methiodide

≥95.0% (HPCE)

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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
Empirical Formula (Hill Notation):
C21H20INO6
CAS Number:
Molecular Weight:
509.29
Beilstein/REAXYS Number:
5419649
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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This Item
14340B7561B7686
(+)-Bicuculline ≥97.0% (TLC)

14340

(+)-Bicuculline

assay

≥95.0% (HPCE)

assay

≥97.0% (TLC)

assay

≥98% (HPLC)

assay

≥97% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

2-8°C

solubility

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

solubility

-

solubility

H2O: >10 mg/mL

solubility

H2O: >10 mg/mL

optical activity

[α]/D -117±7°, c = 1 in chloroform

optical activity

[α]20/D +126±6°, c = 1% in chloroform

optical activity

-

optical activity

-

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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