Basic information
- Standard SMILES
COc1ccc(CN2CCNCC2)c(OC)c1OC.Cl.Cl- InChIKey
VYFLPFGUVGMBEP-UHFFFAOYSA-N- Molecular formula
- C14H24Cl2N2O3
- Average molar mass
- 339.3 g/mol
- Monoisotopic mass
- 338.11639799
Overview
Trimetazidine hydrochloride is an aromatic amine.
Names & identifiers
- Preferred name
- Trimetazidine Dihydrochloride
- IUPAC
- 1-[(2,3,4-trimethoxyphenyl)methyl]piperazine;dihydrochloride
- English name
- Trimetazidine dihydrochloride
- Molecular formula
- C14H24Cl2N2O3
- Molecular weight
- 339.26
Names & synonyms
Show more names
Database identifiers
- CAS
13171-25-0- PubChem CID
- 83201
- DTXSID
DTXSID1045407- ChEMBL
CHEMBL3561076- ChEBI
CHEBI:32262- UNII
- 48V6723Z1P
- EC Number
- 236-117-0
Properties
Computed structural properties
- Topological polar surface area
- 43 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 259
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 231 · 231-235 °C(lit.)
- storage temp.
- Refrigerator
- solubility
- Freely soluble in water, sparingly soluble in alcohol.
- form
- Solid
- color
- White to Off-White
- Merck
- 14 · 14,9705
- Stability
- Hygroscopic
- InChI
- InChI=1S/C14H22N2O3.2ClH/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;2*1H
- InChIKey
- XIRALXKCBGTYSC-UHFFFAOYSA-N
- SMILES
- C1(C=CC(OC)=C(OC)C=1OC)CN1CCNCC1.Cl.Cl
- CAS DataBase Reference
- 13171 · 13171-25-0(CAS DataBase Reference)
- FDA UNII
- 48 V6723Z1P · 48V6723Z1P
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- RTECS
- 2976100 · TM2976100
- HazardClass
- IRRITANT
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Toxicity
- 50 in · LD50 in male, female mice, rats (mg/kg): 91, 107, 124, 124 i.v.; 264, 245, 327, 288 i.p.; 528, 608, 1147, 987 orally (Harpey)
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (98.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 111 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- TM2976100
- hs_code
- 29339900
- Toxicity
- LD50 in male, female mice, rats (mg/kg): 91, 107, 124, 124 i.v.; 264, 245, 327, 288 i.p.; 528, 608, 1147, 987 orally (Harpey)
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- safety_code
- 26-36
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Applications
DescriptionTrimetazidine dihydrochloride is the dihydrochloride salt of Trimetazidine. It is a drug used for the treatment of angina pectoris. It is capable of improving the left ventricular function in diabetic patients suffering coronary heart disease as well as treating the symptoms of patients suffering heart failure of different etiologies. It takes effects through acting as an anti- ischemic metabolic agent being capable of improving the utilization efficiency of myocardial glucose by inhibiting the metabolism of fatty acid (through inhibiting the activity of mitochondrial long- chain 3-ketoacyl coenzyme A Thiolase). The shift from fatty acid oxidation to glucose oxidation optimizes cellular energy process in cells exposed to hypoxia or ischaemia, further maintaining the intracellular ATP levels and ensuring the normal function of ionic pumps and transmembrane sodium-potassium flow to maintain cellular homeostasis.
DescriptionTrimetazidine (hydrochloride) (Item No. 18165) is an analytical reference standard that is structurally categorized as a piperazine. It decreases fatty acid β-oxidation by reversibly inhibiting mitochondrial long-chain 3-ketoacyl thiolase (IC50 = 75 nM). This, in turn, stimulates glucose oxidation. In ischemic heart, trimetazidine reduces ischemia/reperfusion injury in clinical trials. Compounds that reduce mitochondrial fatty acid β-oxidation, including trimetazidine, have shown clinical efficacy against chronic stable angina in clinical trials. In part because of its ability to ameliorate testosterone cardiotoxicity, trimetazidine has been classified as a prohibited substance by the World Anti-Doping Agency. This product is intended for research and forensic applications.
UsesAntianoxic
Uses1-(2,3,4-Trimethoxybenzyl)piperazine dihydrochloride or trimetazidine dihydrochloride can be used as a building block to synthesize: Phenylpropyl trimetazidine derivatives with potent cerebral vasodilator activity.Benzoylguanidine-trimetazidine derivatives for myocardial ischemic-reperfusion activity studies.
UsesCoronary vasodilator. Antianginal
Suppliers50 total
Additional notes
DefinitionChEBI: Trimetazidine hydrochloride is an aromatic amine.
Related reactions
Linked notes
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