14340

(+)-Bicuculline

≥97.0% (TLC)

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

Properties

• 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)

Description

General description

Bicuculline is a convulsant alkaloid.[1] It was originally isolated from the plant Dicentra cucullaria. [2]

Application

Bicuculline has been used:

• as a compound to compare pharmacodynamics and network activity profiles of conolidine/cannabidiol[3]
• to study the effects of chronic caffeine administration on the function of GABA_A receptor[4]
• to isolate N-methyl-D-aspartate receptor (NMDAR)-specific evoked and miniature excitatory postsynaptic currents (eEPSCs and mEPSCs) in neurons of rats[5]

Biochem/physiol Actions

(+)-Bicuculline acts as a competitive inhibitor of GABA liganding binding to the receptor.[6]

(+)-Bicuculline is a GABA_A 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.

Safety Information

• pictograms: GHS06,GHS09
• signalword: Danger
• hcodes: H300 + H310 + H330,H400
• pcodes: P260 - P262 - P273 - P280 - P302 + P352 + P310 - P304 + P340 + P310
• 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
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges