40709-69-1

Basic information

• Product Name: (-)-Bicucullinemethiodide
• Synonyms: [R-(R,S)]-5-(6,8-Dihydro-8-oxofuro[3,4-e]-1,3-benzodioxol-6-yl)-5,6,7,8-tetrahydro-6,6-dimethyl-1,3-dioxolo[4,5-g]isoquinolinium iodide;1,3-Dioxolo(4,5-G)isoquinolinium, 5-((6R)-6,8-dihydro-8-oxofuro(3,4-E)-1,3-benzodioxol-6-yl)-5,6,7,8-tetrahydro-6,6-dimethyl-, iodide, (5S)-;1,3-Dioxolo(4,5-G)isoquinolinium, 5-(6,8-dihydro-8-oxofuro(3,4-E)-1,3-benzodioxol-6-yl)-5,6,7,8-tetrahydro-6,6-dimethyl-, iodide, (R-(R*,S*))-;(5S)-5-[(6R)-6,8-Dihydro-8-oxofuro[3,4-e]-1,3-benzodioxol-6-yl]-5,6,7,8-tetrahydro-6,6-dimethyl-1,3-dioxolo[4,5-g]isoquinolinium iodide
• CAS NO: 40709-69-1
• Molecular Formula: C21H20INO6
• Molecular Weight: 0
• Product Categories: GABA/Glycine receptor
• Mol File: 40709-69-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: Store at RT
• Solubility: H2O: soluble10mg/mL, almost clear, greenish-yellow
• BRN: 5419649
• CAS DataBase Reference: (-)-Bicucullinemethiodide(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Bicucullinemethiodide(40709-69-1)
• EPA Substance Registry System: (-)-Bicucullinemethiodide(40709-69-1)

Safety Data

• WGK Germany: 3
• RTECS: JI4904100
• HazardClass: 6.1
• Hazardous Substances Data: 40709-69-1(Hazardous Substances Data)

Usage

Description

(-)-Bicucullinemethiodide, also known as Bicuculline, is a phthalide isoquinoline alkaloid derived from Dicentra cucullaria. It functions as a gamma-aminobutyric acid (GABA) antagonist and an acetylcholinesterase inhibitor. Bicuculline is known for its ability to block inhibition in semicoronal slices and inhibit slow afterhyperpolarization (AHP).

Uses

Used in Neuroscience Research:
(-)-Bicucullinemethiodide is used as a GABA antagonist for blocking inhibitory neurotransmission in semicoronal slices. This application is crucial for studying the effects of GABA on neuronal activity and understanding the role of GABAergic signaling in the central nervous system.
Used in Organotypic Hippocampal Slice Cultures (OHSCs) Preparation:
(-)-Bicucullinemethiodide is utilized as a GABA antagonist in the preparation of organotypic hippocampal slice cultures. This application aids in the investigation of hippocampal neuronal networks and their responses to various stimuli, contributing to the understanding of learning, memory, and other cognitive functions.

Biological Activity

Methiodide form of classical GABA A receptor antagonist (+)-bicuculline ([R-(R*,S*)]-6-(5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)furo[3,4-e]-1,3-benzodioxol-8(6H)-one ). More water-soluble and stable. Non-GABA receptor-mediated actions reported, including actions on calcium-dependent potassium channels.

Biochem/physiol Actions

(-)-Bicuculline methiodide is a GABAA receptor antagonist, which acts as a competitive inhibitor of GABA ligand binding to the receptor.

InChI:InChI=1/C21H20NO6.HI/c1-22(2)6-5-11-7-15-16(26-9-25-15)8-13(11)18(22)19-12-3-4-14-20(27-10-24-14)17(12)21(23)28-19;/h3-4,7-8,18-19H,5-6,9-10H2,1-2H3;1H/q+1;/p-1/t18-,19+;/m0./s1

Upstream product

• 74-88-4 methyl iodide 
• 485-49-4 bicuculline 

Downstream Products

• 59614-38-9 aobamidine 

Relevant articles and documents

ALKALOIDS FROM Corydalis nobilis (L.) Pers. AND C. intermedia (L.) MERAT

Rhizomes of Corydalis nobilis (L.) Pers. (3percent of alkaloids) contain (+)-tetrahydropalmitine, (+)-bicuculline and (+)-corytuberine as the main constituents of the tertiary alkaloid fraction.Protopine, (+)-corypalmine and (+)-stylopine, which also belong to the dominant alkaloids, were isolated in lesser amounts.As minor alkaloids were isolated (+/-)-tetrahydropalmatine, (+)-corydaline, allocryptopine, cryptopine, (-)-scoulerine, (+)-adlumidine, (+)-sinactine, (+/-)-corlumine, isoboldine, (+)-corybulbine, (+/-)-stylopine and (-)-isocorypalmine.The fraction of quaternary protoberberine alkaloids afforded coptisine, dehydrocorydaline, palmatine, corysamine, jatrorrhyzine and cis-N-methylstylopinium hydroxide.Aobamidine (Z-adlumidiceine enol lactone), isolated as the principal alkaloid of aerial parts (0.3 percent of alkaloids), is obviously an artifact arising from bicuculline N-metho salt during the isolation process.Further dominant alkaloids of the tertiary fraction were adlumidine, bicuculline, protopine, (+/-)-tetrahydropalmatine and (+/-)-corlumine; as minor alkaloids were isolated corytuberine, scoulerine, corypalmine, cryptopine, isocorypalmine, corybulbine, (+)-corydalidzine, and unidentified alkaloids CN 1 (C23H25NO5, m.p.211 deg C) and CN 2 (m.p.261 deg C).Quternary protoberberine fraction afforded coptisine and palmatine.Nineteen of the mentioned alkaloids were isolated froom this species for the first time.Tubers of C.intermedia (L.) Merat (0.7 percent of alkaloids) afforded protopine, tetrahydropalmatine and corydaline as the main alkaloids and allocryptopine, canadine, stylopine, palmatine, dehydrocorydaline, berberine, coptisine as minor alkaloids, together with traces of bicuculline and magnoflorine.Dominant alkaloids of the aerial part (0.73 percent of alkaloids) were bicuculline, bulbocapnine, protopine, stilopine and an unidentified phenolic base, m.p. 258 deg C.Isoboldine, scoulerine, allocryptopine, corydaline, canadine, coptisine, palmatine and berberine were identified as the minor alkaloids.