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14340

Sigma-Aldrich

(+)-Bicuculline

≥97.0% (TLC)

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Synonym(s):
Bucuculline
Empirical Formula (Hill Notation):
C20H17NO6
CAS Number:
Molecular Weight:
367.35
Beilstein:
98786
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥97.0% (TLC)

form

powder

optical activity

[α]20/D +126±6°, c = 1% in chloroform

mp

193-197 °C

SMILES string

[H][C@]1(OC(=O)c2c3OCOc3ccc12)[C@@]4([H])N(C)CCc5cc6OCOc6cc45

InChI

1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1

InChI key

IYGYMKDQCDOMRE-ZWKOTPCHSA-N

Gene Information

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This Item
E1383PHL803715.05875
(+)-Bicuculline ≥97.0% (TLC)

Sigma-Aldrich

14340

(+)-Bicuculline

Etoposide synthetic, 95.0-105.0%, powder

Sigma-Aldrich

E1383

Etoposide

(+)-Bicuculline phyproof® Reference Substance

PHL80371

(+)-Bicuculline

(+)-Bicuculline

Sigma-Aldrich

5.05875

(+)-Bicuculline

form

powder

form

powder

form

-

form

solid

Quality Level

100

Quality Level

200

Quality Level

-

Quality Level

100

optical activity

[α]20/D +126±6°, c = 1% in chloroform

optical activity

-

optical activity

-

optical activity

-

mp

193-197 °C

mp

236-251 °C (lit.)

mp

-

mp

-

Gene Information

rat ... Gabra2(29706)

Gene Information

human ... ABCB1(5243), CYP3A4(1576), TOP2A(7153), TOP2B(7155)
mouse ... Abcb1a(18671), Abcb1b(18669)
rat ... Top2a(360243)

Gene Information

-

Gene Information

-

General description

Bicuculline is a convulsant alkaloid. It was originally isolated from the plant Dicentra cucullaria.

Application

Bicuculline has been used:
  • as a compound to compare pharmacodynamics and network activity profiles of conolidine/cannabidiol
  • to study the effects of chronic caffeine administration on the function of GABAA receptor
  • to isolate N-methyl-D-aspartate receptor (NMDAR)-specific evoked and miniature excitatory postsynaptic currents (eEPSCs and mEPSCs) in neurons of rats

Biochem/physiol Actions

(+)-Bicuculline acts as a competitive inhibitor of GABA liganding binding to the receptor.
(+)-Bicuculline is a GABAA receptor antagonist.

Features and Benefits

This compound is featured on the GABAC Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbonesEnvironment

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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