13171-25-0

Basic information

• Product Name: Trimetazidine dihydrochloride
• Synonyms: 1-(2,3,4-TRIMETHOXYBENZYL)PIPERAZINE DIHYDROCHLORIDE;TRIMETAZIDINE DI HCL;TRIMETAZIDINE DIHYDROCHLORIDE;TRIMETAZIDINE HYDROCHLORIDE;TRIMETAZIDINE 2HCL;1-((2,3,4-trimethoxyphenyl)methyl)-piperazindihydrochloride;1-(2,3,4-trimethoxybenzyl)-piperazindihydrochloride;kyurinett
• CAS NO: 13171-25-0
• Molecular Formula: C₁₄H₂₂N₂O₃*2ClH
• Molecular Weight: 339.26
• EINECS: 236-117-0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;C14 to C15;Chemical Synthesis;Heterocyclic Building Blocks;Piperazines
• Mol File: 13171-25-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 231-235 °C(lit.)
• Boiling Point: 364 °C at 760 mmHg
• Flash Point: 174 °C
• Appearance: crystalline solid
• Vapor Pressure: 1.73E-05mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: Freely soluble in water, sparingly soluble in alcohol.
• Stability: Hygroscopic
• Merck: 14,9705
• CAS DataBase Reference: Trimetazidine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Trimetazidine dihydrochloride(13171-25-0)
• EPA Substance Registry System: Trimetazidine dihydrochloride(13171-25-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: TM2976100
• HazardClass: IRRITANT
• Hazardous Substances Data: 13171-25-0(Hazardous Substances Data)

Usage

Description

Trimetazidine dihydrochloride, also known as 1-(2,3,4-Trimethoxybenzyl)piperazine dihydrochloride, is the dihydrochloride salt of Trimetazidine. It is a crystalline solid that functions as an anti-ischemic metabolic agent. Trimetazidine dihydrochloride is used for the treatment of angina pectoris and can improve left ventricular function in diabetic patients with coronary heart disease, as well as treat symptoms of heart failure of various etiologies. It operates by enhancing the utilization efficiency of myocardial glucose and inhibiting the metabolism of fatty acids, thereby optimizing cellular energy processes in cells exposed to hypoxia or ischemia.

Uses

Used in Pharmaceutical Industry:
Trimetazidine dihydrochloride is used as an antianoxic agent for the treatment of angina pectoris, improving left ventricular function in diabetic patients with coronary heart disease, and treating heart failure symptoms of different etiologies. It achieves this by inhibiting the metabolism of fatty acids and promoting glucose oxidation, which optimizes cellular energy processes in hypoxic or ischemic conditions.
Used in Coronary Vasodilation:
Trimetazidine dihydrochloride is used as a coronary vasodilator and antianginal agent, helping to alleviate symptoms of angina pectoris and improve blood flow to the heart.
Used in Synthesis of Cerebral Vasodilators:
Trimetazidine dihydrochloride is used as a building block to synthesize phenylpropyl trimetazidine derivatives with potent cerebral vasodilator activity, which can be beneficial in the treatment of conditions related to restricted blood flow in the brain.
Used in Myocardial Ischemic-Reperfusion Activity Studies:
Trimetazidine dihydrochloride is used in the synthesis of benzoylguanidine-trimetazidine derivatives for studying their potential in myocardial ischemic-reperfusion activity, which could be significant for developing treatments for heart conditions related to blood flow restoration after a period of ischemia.
Used in Research and Forensic Applications:
Trimetazidine dihydrochloride serves as an analytical reference standard in research and forensic applications, particularly in the study of its effects on mitochondrial long-chain 3-ketoacyl thiolase and its potential role in reducing ischemia/reperfusion injury in the heart.

References

Fragasso, G, et al. "A randomized clinical trial of trimetazidine, a partial free fatty acid oxidation inhibitor, in patients with heart failure. " Journal of the American College of Cardiology 48.5 (2006):992. Tuunanen, H, et al. "Trimetazidine, a metabolic modulator, has cardiac and extracardiac benefits in idiopathic dilated cardiomyopathy."Circulation 118.12(2008):1250. Kantor, P. F., et al. "The antianginal drug trimetazidine shifts cardiac energy metabolism from fatty acid oxidation to glucose oxidation by inhibiting mitochondrial long-chain 3-ketoacyl coenzyme A thiolase."Circulation Research 86.5(2000):580. Stanley, W. C., and M. Marzilli. "Metabolic therapy in the treatment of ischaemic heart disease: the pharmacology of trimetazidine. "Fundamental & Clinical Pharmacology 17.2(2003):133–145. Kantor, Paul F., et al. "The antianginal drug trimetazidine shifts cardiac energy metabolism from fatty acid oxidation to glucose oxidation by inhibiting mitochondrial long-chain 3-ketoacyl coenzyme A thiolase." Circulation research 86.5 (2000): 580-588.

InChI:InChI=1/C14H22N2O3/c1-17-12-5-4-11(13(18-2)14(12)19-3)10-16-8-6-15-7-9-16/h4-5,15H,6-10H2,1-3H3/p+2

Upstream product

• 110-85-0 piperazine 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 

Downstream Products

• 120697-50-9 1-<2-(pyrrolidino)ethyl>-4-(2,3,4-trimethoxybenzyl)piperazine 
• 64966-11-6 1-((E)-3-Phenyl-allyl)-4-(2,3,4-trimethoxy-benzyl)-piperazine; hydrochloride 
• 113743-20-7 1-(pyrrolidinocarbonylmethyl)-4-(2,3,4-trimethoxybenzyl)piperazine 
• 119963-54-1 1-Piperidin-1-yl-2-[4-(2,3,4-trimethoxy-benzyl)-piperazin-1-yl]-ethanone 
• 119963-53-0 N,N-Dipropyl-2-[4-(2,3,4-trimethoxy-benzyl)-piperazin-1-yl]-acetamide 
• 114022-14-9 1-Di-p-tolylmethyl-4-(2,3,4-trimethoxy-benzyl)-piperazine; hydrochloride 
• 114022-15-0 1-[Bis-(4-methoxy-phenyl)-methyl]-4-(2,3,4-trimethoxy-benzyl)-piperazine; compound with (E)-but-2-enedioic acid 
• 114055-20-8 1--4-(2,3,4-trimethoxybenzyl)piperazine dihydrochloride hydrate 
• 119963-56-3 N-Benzyl-2-[4-(2,3,4-trimethoxy-benzyl)-piperazin-1-yl]-acetamide 
• 113696-51-8 1-(3,4-dichlorocinnamyl)-4-(2,3,4-trimethoxybenzyl)piperazine dihydrochloride 
• 114022-18-3 1-[(4-Methoxy-phenyl)-phenyl-methyl]-4-(2,3,4-trimethoxy-benzyl)-piperazine; compound with (E)-but-2-enedioic acid 
• 119976-97-5 N-Cyclohexyl-2-[4-(2,3,4-trimethoxy-benzyl)-piperazin-1-yl]-acetamide 
• 76925-19-4 1-(4-Chloro-phenyl)-3-[4-(2,3,4-trimethoxy-benzyl)-piperazin-1-yl]-propan-1-one; hydrochloride 
• 119963-55-2 N-phenyl-2-(4-(2,3,4-trimethoxybenzyl)piperazin-1-yl)acetamide 

Relevant articles and documents

Synthesis method of trimetazidine hydrochloride

The invention provides a synthesis method of trimetazidine hydrochloride, which comprises the following steps: carrying out hydroamination reaction by using 2,3,4-trimethoxybenzaldehyde and piperazineanhydrous as raw materials, and catalyzing by using a Lindlar catalyst. The trimetazidine hydrochloride produced by the method does not contains trimetazidine hydrochloride impurity B and has high purity.