Apovincamine

Base Information

• Chemical Name: Apovincamine
• CAS No.: 4880-92-6
• Molecular Formula: C21H24 N2 O2
• Molecular Weight: 336.434
• Hs Code.: 2939800000
• European Community (EC) Number: 225-491-0
• UNII: 504R182ZX7
• DSSTox Substance ID: DTXSID401023598
• Nikkaji Number: J8.835H
• Wikipedia: Apovincamine
• Wikidata: Q15410269
• NCI Thesaurus Code: C74413
• Metabolomics Workbench ID: 67854
• ChEMBL ID: CHEMBL1163488
• Mol file: 4880-92-6.mol

Synonyms:apovincamine;apovincamine, (16alpha)-isomer

Chemical Property of Apovincamine

Chemical Property:

• Vapor Pressure: 8.61E-07mmHg at 25°C
• Melting Point: 160-162℃
• Boiling Point: 405.7°Cat760mmHg
• Flash Point: 199.1°C
• PSA: 34.47000
• Density: 1.3g/cm³
• LogP: 3.69610
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 336.183778013
• Heavy Atom Count: 25
• Complexity: 603

Purity/Quality:

NLT 98% ^*data from raw suppliers

cis-Apovincamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OC
• Isomeric SMILES: CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OC
• Uses: cis-Apovincamine (Vinpocetine USP Related Compound B), is a vinca alkaloid and a chemical precursor of Vinpocetine (V332500), a derivative of Vincamine with vasodilating activity. Vasodilator (cerebral).
• Therapeutic Function: Vasodilator

Technology Process of Apovincamine

There total 70 articles about Apovincamine 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: 95.0%

vincamin (1617-90-9) → apovincamine (4880-92-6)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 2h; Dean-Stark; Reflux; Inert atmosphere;

DOI:10.1021/acs.jmedchem.9b01924

Reference yield: 88.0%

(-)-methyl 1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine(1β-yl) pyruvate oxime (85588-92-7) → apovincamine (4880-92-6)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 1.5h; Heating;

Reference yield: 83.5%

(1R,5S,12bS)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-carbaldehyde + methyl chloroacetate (96-34-4) → apovincamine (4880-92-6)

Guidance literature:

With sodium methylate; In tetrahydrofuran; at -10 - -5 ℃;

upstream raw materials:

(-)-criocerine

methanol

(3S,17S)-14-oxo-15-hydroxyimino-E-homoeburnane

(-)-vincadifformine

Downstream raw materials:

deoxyvincamine

Apovincaminic acid

Refernces

• 1、 Chen, Jing,Du, Te,Hu, Lihong,Liu, Xinpeng,Lv, Xue,Shen, Xu,Sun, Guanglong,Wang, Jiaying,Wang, Junwei,Xu, Jiawen. "Design, synthesis and biological evaluation of vincamine derivatives as potential pancreatic β-cells protective agents for the treatment of type 2 diabetes mellitus". . . Retrieved 2020/01/08.
• 2、 -. "ANALOGS OF VINCAMINE AND USES THEREOF". Paragraph 00336; 00379. . Retrieved 2018/09/12.