Trimetazidine

Base Information

• Chemical Name: Trimetazidine
• CAS No.: 5011-34-7
• Molecular Formula: C14H22N2O3
• Molecular Weight: 266.34
• Hs Code.: 2933599090
• European Community (EC) Number: 225-690-2
• UNII: N9A0A0R9S8
• DSSTox Substance ID: DTXSID2048531
• Nikkaji Number: J8.797A
• Wikipedia: Trimetazidine
• Wikidata: Q674703
• NCI Thesaurus Code: C76590
• Metabolomics Workbench ID: 152124
• ChEMBL ID: CHEMBL203266
• Mol file: 5011-34-7.mol

Synonyms:Centrophène;Dihydrochloride, Trimetazidine;Idaptan;Trimétazidine Irex;Trimetazidine;Trimetazidine Dihydrochloride;Vasartel;Vastarel

Chemical Property of Trimetazidine

Chemical Property:

• Appearance/Colour: hite or off-white crystalline powder
• Vapor Pressure: 0.003Pa at 25℃
• Melting Point: 200 - 205oC
• Boiling Point: 364 °C at 760 mmHg
• PKA: 9.07±0.10(Predicted)
• Flash Point: 174 °C
• PSA: 42.96000
• Density: 1.092 g/cm³
• LogP: 1.38430
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility.: Chlorofrom (Slightly), Methanol (Slightly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 266.16304257
• Heavy Atom Count: 19
• Complexity: 259

Purity/Quality:

99.9% ^*data from raw suppliers

1-(2,3,4-Trimethoxybenzyl)piperazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C(=C(C=C1)CN2CCNCC2)OC)OC
• Recent ClinicalTrials: The Effect of Trimetazidine on Mitochondrial Function, Myocardial Performance, and Invasive Hemodynamics in Patients Diagnosed With Wild-Type Transthyretin Cardiac Amyloidosis
• Recent EU Clinical Trials: Evaluation of the cardioprotective metabolic effect of trimetazidine in patients with myocardial ischaemia
• Uses: 1-(2,3,4-Trimethoxybenzyl)piperazine is used in combination with atorvastatin in the treatment of coronary heart disease and angina pectoris.
• Therapeutic Function: Coronary vasodilator

Technology Process of Trimetazidine

There total 6 articles about Trimetazidine 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: 92.1%

2,3,4-trimethoxybenzyl chloride (1133-49-9) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → 1-(2,3,4-trimethoxybenzyl)piperazine (5011-34-7)

Guidance literature:

2,3,4-trimethoxybenzyl chloride; 1-t-Butoxycarbonylpiperazine; With methanol; sodium hydroxide; at 35 - 45 ℃; for 4h;

With hydrogenchloride; In water; at 35 - 45 ℃; for 2h;

Reference yield:

4-(2,3,4-trimethoxy-benzyl)-piperazine-1-carboxylic acid ethyl ester (53531-01-4) → 1-(2,3,4-trimethoxybenzyl)piperazine (5011-34-7)

Guidance literature:

With potassium hydroxide; In ethanol; at 130 ℃; for 2.5h;

DOI:10.1021/jm981064b

Reference yield:

2,3,4-trimethoxybenzaldehyde (2103-57-3) → 1-(2,3,4-trimethoxybenzyl)piperazine (5011-34-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₃CN, AcOH / 16 h / Ambient temperature

2: aq. KOH / ethanol / 2.5 h / 130 °C

With potassium hydroxide; sodium cyanoborohydride; acetic acid; In ethanol;

DOI:10.1021/jm981064b

upstream raw materials:

4-(2,3,4-trimethoxy-benzyl)-piperazine-1-carboxylic acid ethyl ester

2,3,4-trimethoxybenzaldehyde

2,3,4-trimethoxybenzyl chloride

1-t-Butoxycarbonylpiperazine

Downstream raw materials:

1-cyano-{2-[4-(2,3,4-trimethoxybenzyl)piperazin-1-yl]carbonyl}cyclopropane

KB-2796 dihydrochloride

Refernces

• 1、 Long, Huan,Hu, Xiaolong,Wang, Baolin,Wang, Quan,Wang, Rong,Liu, Shumeng,Xiong, Fei,Jiang, Zhenzhou,Zhang, Xiao-Qi,Ye, Wen-Cai,Wang, Hao. "Discovery of Novel Apigenin-Piperazine Hybrids as Potent and Selective Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors for the Treatment of Cancer". . p. 12089 - 12108. Retrieved 2021/09/06.
• 2、 Ferté, Jacques,Kühnel, Jean-Marc,Chapuis, Geneviève,Rolland, Yves,Lewin, Guy,Schwaller, Marc A.. "Flavonoid-related modulators of multidrug resistance: Synthesis, pharmacological activity, and structure-activity relationships". . p. 478 - 489. Retrieved 2007/10/03.