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Merck

14340

Sigma-Aldrich

(+)-Bicucullin

≥97.0% (TLC)

Synonym(e):

Bucucullin

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About This Item

Empirische Formel (Hill-System):
C20H17NO6
CAS-Nummer:
Molekulargewicht:
367.35
Beilstein:
98786
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352200
PubChem Substanz-ID:
NACRES:
NA.77

Qualitätsniveau

Assay

≥97.0% (TLC)

Form

powder

Optische Aktivität

[α]20/D +126±6°, c = 1% in chloroform

mp (Schmelzpunkt)

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

InChIKey

IYGYMKDQCDOMRE-ZWKOTPCHSA-N

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Allgemeine Beschreibung

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

Anwendung

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. Wirkung

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

Leistungsmerkmale und Vorteile

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.

Piktogramme

Skull and crossbonesEnvironment

Signalwort

Danger

Gefahreneinstufungen

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

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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


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Die Dokumentenbibliothek aufrufen

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)
Evidence for naloxone and opiates as GABA antagonists
E. Breuker et al.
British Journal of Pharmacology, 58, 458-458 (1976)
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)
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)

Artikel

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