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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/REAXYS Number:
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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1 of 4

This Item
E1383PHL8037114343
vibrant-m

14340

(+)-Bicuculline

vibrant-m

E1383

Etoposide

vibrant-m

PHL80371

(+)-Bicuculline

Quality Level

100

Quality Level

200

Quality Level

-

Quality Level

100

form

powder

form

powder

form

-

form

powder

optical activity

[α]20/D +126±6°, c = 1% in chloroform

optical activity

-

optical activity

-

optical activity

[α]/D -117±7°, c = 1 in chloroform

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

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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Neurotoxicology and Teratology, 63(2), 1-8 (2017)
Evidence that bicuculline and picrotoxin act at separate sites to antagonize gamma-aminobutyric acid in rat cuneate nucleus.
M A Simmonds
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