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14340

Sigma-Aldrich

(+)-Bicuculline

≥97.0% (TLC)

Sinonimo/i:

Bucuculline

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About This Item

Formula empirica (notazione di Hill):
C20H17NO6
Numero CAS:
485-49-4
Peso molecolare:
367.35
Beilstein:
98786
Numero CE:
207-619-7
Numero MDL:
MFCD00005006
Codice UNSPSC:
12352200
ID PubChem:
329750455
NACRES:
NA.77

Livello qualitativo

100

Saggio

≥97.0% (TLC)

Forma fisica

powder

Attività ottica

[α]20/D +126±6°, c = 1% in chloroform

Punto di fusione

193-197 °C

Stringa SMILE

[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
IYGYMKDQCDOMRE-ZWKOTPCHSA-N

Informazioni sul gene

rat ... Gabra2(29706)

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Descrizione generale

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

Applicazioni

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

Azioni biochim/fisiol

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

Caratteristiche e vantaggi

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.

Pittogrammi

Skull and crossbonesEnvironment
GHS06,GHS09

Avvertenze

Danger

Indicazioni di pericolo

H300 + H310 + H330,H400

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

Choose from one of the most recent versions:

Certificati d'analisi (COA)

Lot/Batch Number
BCCL4705
BCCK4310
BCCC1189
BCBV8509
BCBV5111

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Picrotoxin, Anamirta cocculin A potent antagonist of GABA receptors (IC₅₀ = 240 nM) at synapses in the central nervous system.

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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 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)
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