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14340

(+)-Bicuculline

≥97.0% (TLC), GABAA receptor antagonist, powder

Synonym(s):

Bucuculline

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About This Item

Empirical Formula (Hill Notation):
C20H17NO6
CAS Number:
485-49-4
Molecular Weight:
367.35
NACRES:
NA.77
PubChem Substance ID:
329750455
UNSPSC Code:
12352200
EC Number:
207-619-7
MDL number:
MFCD00005006
Beilstein/REAXYS Number:
98786
Assay:
≥97.0% (TLC)
Form:
powder
Quality level:
100
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Product Name

(+)-Bicuculline, ≥97.0% (TLC)

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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1 of 1

This Item
PHL803715.05875P3510
(+)-Bicuculline ≥97.0% (TLC)

Sigma-Aldrich

14340

(+)-Bicuculline

(+)-Bicuculline phyproof® Reference Substance

PHL80371

(+)-Bicuculline

(+)-Bicuculline

Sigma-Aldrich

5.05875

(+)-Bicuculline

Papaverine hydrochloride powder

Sigma-Aldrich

P3510

Papaverine hydrochloride

form

powder

form

-

form

solid

form

powder

assay

≥97.0% (TLC)

assay

≥98.0% (HPLC)

assay

≥98% (HPLC)

assay

≥98%

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

100

mp

193-197 °C

mp

-

mp

-

mp

-

Gene Information

rat ... Gabra2(29706)

Gene Information

-

Gene Information

-

Gene Information

human ... PDE4B(5142)

optical activity

[α]20/D +126±6°, c = 1% in chloroform

optical activity

-

optical activity

-

optical activity

-

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.[1]
(+)-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

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

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6938
BCCM8459
BCCL4705
BCCK4310
BCCC1189

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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)
S Ueno et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 17(2), 625-634 (1997-01-15)
Anesthetic drugs are known to interact with GABAA receptors, both to potentiate the effects of low concentrations of GABA and to directly gate open the ion channel in the absence of GABA; however, the site(s) involved in direct gating by
Evidence for naloxone and opiates as GABA antagonists
E. Breuker et al.
British Journal of Pharmacology, 58, 458-458 (1976)
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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Global Trade Item Number

SKUGTIN
14340-500MG04061838734815
14340-25MG04061838734808
14340-100MG04061838734792
14340-500M04061837383045

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