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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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

14343-50MG:4548173985909
14343-VAR:
14343-250MG:
14343-10MG:4548173985893
14343-BULK:

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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