14340

Sigma-Aldrich

(+)-Bicuculline

≥97.0% (TLC)

Sinónimos:
Bucuculline
Empirical Formula (Hill Notation):
C20H17NO6
Número de CAS:
Peso molecular:
367.35
Beilstein/REAXYS Number:
98786
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥97.0% (TLC)

optical activity

[α]20/D +126±6°, c = 1% in chloroform

mp

193-197 °C

storage temp.

2-8°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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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

hazcat

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 Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificado de Análisis

Certificado de origen

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)
Herbal products and GABA receptors
Johnston GAR, et al.
Encyclopedia of Neuroscience, 169(2), 1095-1101 (2009)
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)
Evidence for naloxone and opiates as GABA antagonists
E. Breuker et al.
British Journal of Pharmacology, 58, 458-458 (1976)
Artículos
Yeast is one of the most important microorganisms known and utilised by mankind. Ancient Middle Eastern civilisations used the organism to bake bread and to produce mead, beer and wine.
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