(+)-Bicuculline CAS 485-49-4

Introduction：Basic information about (+)-Bicuculline CAS 485-49-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

(+)-Bicuculline Basic information

• Product Name: (+)-Bicuculline
• Synonyms: 5-g)isoquinolin-5-yl)-,(r-(r*,s*))-lo(;bicucullin;Bucuculline;d-Bicuculline/(+)-Bicuculline;D-alkali than buttoned Spirit;Furo[3,4-e]-1,3-benzodioxol-8(6H)-one, 6-[(5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (6R)-;6-[(5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-(6R)-furo[3,4-e]-1,3-benzodioxol-8(6H)-one;(+)-Bicuculline, 99%, a GABAA antagonist
• CAS: 485-49-4
• MF: C20H17NO6
• MW: 367.35
• EINECS: 207-619-7
• Product Categories: Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Alkaloids;Intermediates & Fine Chemicals;Pharmaceuticals;GABA/Glycine receptor;GABA
• Mol File: 485-49-4.mol

(+)-Bicuculline Chemical Properties

• Melting point: 193-197 °C
• alpha: D25 +130.5° (CHCl3)
• Boiling point: 497.92°C (rough estimate)
• density: 1.3694 (rough estimate)
• refractive index: 1.5600 (estimate)
• storage temp.: 2-8°C
• solubility: Benzene, Chloroform, DMSO, Ethyl Acetate
• pka: 4.84(at 25℃)
• form: Off-white to yellow powder.
• color: Pale Yellow
• Optical Rotation: [α]20/D +126±6°, c = 1% in chloroform
• λmax: 325nm(lit.)
• Merck: 14,1203
• BRN: 98786
• 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
• InChIKey: IYGYMKDQCDOMRE-ZWKOTPCHSA-N
• SMILES: [H][C@]1(OC(=O)c2c3OCOc3ccc12)[C@@]4([H])N(C)CCc5cc6OCOc6cc45
• CAS DataBase Reference: 485-49-4(CAS DataBase Reference)
• EPA Substance Registry System: Furo[3,4-e]-1,3-benzodioxol-8(6H)-one, 6-[(5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (6R)- (485-49-4)

Safety Information

• Hazard Codes: T,N,Xn
• Risk Statements: 23/24/25-50-36/37/38-20/21/22
• Safety Statements: 36/37-45-61-36-26
• RIDADR: UN 1544 6.1/PG 2
• WGK Germany: 3
• RTECS: LV0909840
• F: 10-23
• HazardClass: 6.1(b)
• PackingGroup: III
• HS Code: 29399990
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
• Hazard Classifications: Acute Tox. 2 Dermal Acute Tox. 2 Inhalation Acute Tox. 2 Oral Aquatic Acute 1
• Toxicity: LD50 ipr-mus: 8480 mg/kg CUTOEX 1,199,93

(+)-Bicuculline Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

GABAA receptor antagonist.

Uses

GABAa antagonist

Uses

Alkaloid naturally occurring in the d-form. Shows GABA antagonist activity.

Definition

ChEBI: Bicuculline is a benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species. It has a role as an agrochemical, a central nervous system stimulant, a GABA-gated chloride channel antagonist, a neurotoxin and a GABAA receptor antagonist. It is an isoquinoline alkaloid, a member of isoquinolines and a benzylisoquinoline alkaloid.

General Description

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

Biological Activity

Classical GABA A antagonist.

Biochem/physiol Actions

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

Safety Profile

A poison by intraperitoneal route.When heated to decomposition it emits toxic vapors ofNOx.

storage

+4°C

Purification Methods

It crystallises from CHCl3/MeOH as plates. The crystals melt at 177o, then solidify and re-melt at 193-195o [Manske Canad J Research 21B 13 1943]. It is soluble in CHCl3, *C6H6, EtOAc but sparingly soluble in EtOH, MeOH and Et2O. [Stereochem: Blaha et al. Collect Czech Chem Commun 29 2328 1964, Snatzke et al. Tetrahedron 25 5059 1969, Pharmcol: Curtis et al. Nature 266 1222 1970, Beilstein 27 III/IV 1900].