Bicuculline

Base Information

• Chemical Name: Bicuculline
• CAS No.: 485-49-4
• Molecular Formula: C20H17NO6
• Molecular Weight: 367.358
• Hs Code.: 29399990
• European Community (EC) Number: 207-619-7
• NSC Number: 32192
• UNII: Y37615DVKC
• DSSTox Substance ID: DTXSID3042687
• Nikkaji Number: J108.007E
• Wikipedia: Bicuculline
• Wikidata: Q3639734
• Pharos Ligand ID: 263666RY14Q4
• Metabolomics Workbench ID: 53006
• ChEMBL ID: CHEMBL417990
• Mol file: 485-49-4.mol

Synonyms: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;Bicuculline

Chemical Property of Bicuculline

Chemical Property:

• Appearance/Colour: pale yellow solid
• Vapor Pressure: 7.98E-12mmHg at 25°C
• Melting Point: 193-197 °C
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 542.3 °C at 760 mmHg
• PKA: 4.84(at 25℃)
• Flash Point: 281.8 °C
• PSA: 66.46000
• Density: 1.473 g/cm³
• LogP: 2.52260
• Storage Temp.: 0-6°C
• Solubility.: Benzene, Chloroform, DMSO, Ethyl Acetate
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 367.10558726
• Heavy Atom Count: 27
• Complexity: 615

Purity/Quality:

98%,99%, ^*data from raw suppliers

Bicuculline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N, Xn
• Hazard Codes: T,N,Xn
• Statements: 23/24/25-50-36/37/38-20/21/22
• Safety Statements: 36/37-45-61-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C=C2C1C4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3
• Isomeric SMILES: CN1CCC2=CC3=C(C=C2[C@H]1[C@H]4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3
• Uses: GABAA receptor antagonist. GABAa antagonist Alkaloid naturally occurring in the d-form. Shows GABA antagonist activity.

Technology Process of Bicuculline

There total 14 articles about Bicuculline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (+)-Norbicuculline (185022-39-3) → bicuculline (485-49-4)

Guidance literature:

With formic acid; at 100 ℃; for 0.25h;

DOI:10.1016/0223-5234(96)83969-9

Reference yield:

(+/-)-bicuculline (56083-00-2) → bicuculline (485-49-4)

Guidance literature:

With L-(-)-tartaric acid;

DOI:10.1038/165529a0

Reference yield:

8-oxo-6,8-dihydro-[1,3]dioxolo[4,5-e]isobenzofuran-6-carboxylic acid (64395-07-9) → bicuculline (485-49-4)

Guidance literature:

Multi-step reaction with 5 steps

1: thionyl chloride / benzene / 2 h / Heating

2: aq. NaOH / benzene / 1 h

3: 76 percent / POCl₃ / 1 h / 100 °C

4: NaBH₄, AcOH / CH₂Cl₂ / 4 h / 0 - 5 °C

5: 81 percent / HCOOH / 0.25 h / 100 °C

With sodium hydroxide; sodium tetrahydroborate; formic acid; thionyl chloride; acetic acid; trichlorophosphate; In dichloromethane; benzene;

DOI:10.1016/0223-5234(96)83969-9

upstream raw materials:

(-)-Bicuculline

dichloromethane

(-)-β-hydrastine

(S)-3-((R)-6,7-dihydroxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-6,7-dihydroxy-3H-isobenzofuran-1-one

Downstream raw materials:

(4-{[(S)-6-Methyl-5-((R)-8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-9-ylmethyl]-carbamoyl}-phenyl)-carbamic acid tert-butyl ester

aobamidine

bicuculline methiodide

Refernces

• 1、 Haworth,Pinder,Robinson. "-". . p. 529. Retrieved 1950.