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14340

Sigma-Aldrich

(+)-Bicuculline

≥97.0% (TLC)

Synonym(s):

Bucuculline

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About This Item

Empirical Formula (Hill Notation):
C20H17NO6
CAS Number:
485-49-4
Molecular Weight:
367.35
Beilstein:
98786
EC Number:
207-619-7
MDL number:
MFCD00005006
UNSPSC Code:
12352200
PubChem Substance ID:
329750455
NACRES:
NA.77

Quality Level

100

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

rat ... Gabra2(29706)

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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
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H400

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCL4705
BCCK4310
BCCC1189
BCBV8509
BCBV5111

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Evidence for naloxone and opiates as GABA antagonists
E. Breuker et al.
British Journal of Pharmacology, 58, 458-458 (1976)
Herbal products and GABA receptors
Johnston GAR, et al.
Encyclopedia of Neuroscience, 169(2), 1095-1101 (2009)
Discovering the pharmacodynamics of conolidine and cannabidiol using a cultured neuronal network based workflow
Mendis GDC, et al.
Scientific reports, 9(1), 121-121 (2019)
Prolonged ketamine exposure induces increased activity of the GluN2B-containing N-methyl-D-aspartate receptor in the anterior cingulate cortex of neonatal rats
Kokane SS, et al.
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
Neuropharmacology, 19(1), 39-45 (1980-01-01)
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