Argemonine

Base Information

• Chemical Name: Argemonine
• CAS No.: 5531-95-3
• Molecular Formula: C21H25 N O4
• Molecular Weight: 355.434
• NSC Number: 645246,148823,148822,148821
• DSSTox Substance ID: DTXSID90937134
• Wikidata: Q27146596
• ChEMBL ID: CHEMBL1964569
• Mol file: 5531-95-3.mol

Synonyms:argemonine;argemonine hemihydrate

Chemical Property of Argemonine

Chemical Property:

• Vapor Pressure: 3.76E-08mmHg at 25°C
• Melting Point: 132 °C
• Boiling Point: 446°C at 760 mmHg
• PKA: 6.55±0.20(Predicted)
• Flash Point: 125.2°C
• PSA: 40.16000
• Density: 1.156g/cm³
• LogP: 3.48530
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 355.17835828
• Heavy Atom Count: 26
• Complexity: 447

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CC3=CC(=C(C=C3C1CC4=CC(=C(C=C24)OC)OC)OC)OC
• Uses: (-)-Argemonine is a pavine alkaloid that has shown some cytotoxic and anti-HIV activity.

Technology Process of Argemonine

There total 11 articles about Argemonine 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: 86.0%

N-Formylpavine → N-methylpavine (5531-95-3,6901-16-2,16584-62-6)

Guidance literature:

With borane-THF; In tetrahydrofuran; for 4h; Heating;

DOI:10.1039/P19960000907

Reference yield: 64.5%

1,2-dihydro-2-methylpapaverine (2246-26-6,47488-71-1) → 1,2-dimethoxy-4-methylbenzene (494-99-5) + N-methylpavine (5531-95-3)

Guidance literature:

With hydrogenchloride; formic acid; at 85 ℃; for 4h; DCOOH, EtOH, 2 N HCl, 70 deg C, 170 min;

Reference yield: 64.0%

C22H25NO6 → N-methylpavine (5531-95-3,6901-16-2,16584-62-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 24 ℃; Inert atmosphere; Reflux;

DOI:10.1246/cl.190809

upstream raw materials:

1,2-dihydro-2-methylpapaverine

formaldehyd

formic acid

3,4-dimethoxyphenylacetaldehyde

Downstream raw materials:

(+/-)-N-Benzyl-pavinmethin

4',5',4'',5''-Tetramethoxy-7-benzylmethyl-amino-dibenzo<1.2,5.6>cyclooctatrien-(1,3,5)

Refernces

• 1、 Shinohara, Tatsumi,Takeda, Akira,Toda, Jun,Sano, Takehiro. "A new regioselective synthesis of isopavine and pavine alkaloids via double cyclization of N-(1,2-diarylethyl)-N-(2-phenylsulfinylethyl)formamide". . p. 981 - 992. Retrieved 2007/10/03.
• 2、 Langhals, Elke,Langhals, Heinz,Ruechardt, Christoph. "Evidence for a Radical Chain Mechanism for the Knabe Reaction of 1,2-Dihydro-2-methylpapaverine". . p. 1436 - 1454. Retrieved 2007/10/02.