Metoprolol

Base Information

• Chemical Name: Metoprolol
• CAS No.: 51384-51-1
• Deprecated CAS: 54163-88-1,37350-58-6
• Molecular Formula: C15H25 N O3
• Molecular Weight: 267.368
• Hs Code.: 2922509090
• European Community (EC) Number: 253-483-7,257-166-4
• UNII: GEB06NHM23
• DSSTox Substance ID: DTXSID2023309
• Nikkaji Number: J31.137E
• Wikipedia: Metoprolol
• Wikidata: Q409468
• NCI Thesaurus Code: C61845
• RXCUI: 6918
• Pharos Ligand ID: L4D1FYPSTQQJ
• Metabolomics Workbench ID: 37939
• ChEMBL ID: CHEMBL13
• Mol file: 51384-51-1.mol

Synonyms:Beloc Duriles;Beloc-Duriles;Betaloc;Betaloc Astra;Betaloc-Astra;Betalok;CGP 2175;CGP-2175;CGP2175;H 93 26;H 93-26;H 9326;Lopressor;Metoprolol;Metoprolol CR XL;metoprolol CR-XL;metoprolol succinate;Metoprolol Tartrate;Seloken;Spesicor;Spesikor;Toprol;Toprol XL;Toprol-XL

Chemical Property of Metoprolol

Chemical Property:

• Vapor Pressure: 1.02E-17mmHg at 25°C
• Melting Point: 35 °C
• Boiling Point: 398.6 °C at 760 mmHg
• PKA: pKa 9.56± 0.01(H2O,t =25,I=0.15(KCl))(Approximate)
• Flash Point: 194.9 °C
• PSA: 50.72000
• Density: 1.033 g/cm³
• LogP: 2.00410
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 267.18344366
• Heavy Atom Count: 19
• Complexity: 215

Purity/Quality:

99% ^*data from raw suppliers

racMetoprolol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Beta-Adrenergic Receptor Antagonists
• Canonical SMILES: CC(C)NCC(COC1=CC=C(C=C1)CCOC)O
• Recent ClinicalTrials: Metoprolol in Acute Respiratory Distress Syndrome (MAIDEN)
• Recent EU Clinical Trials: Novel therapeutic strategies to reduce coronary microvascular obstruction and to OPTImize non-culprit stenoses revascularization in ST-Elevation acute Myocardial Infarction
• Recent NIPH Clinical Trials: Conparision of transdermal patch beta1 blocker or oral medication on Coronary Computed Tomography Angiography
• Uses: Anti-adrenergic. rac Metoprolol is a β1 selective aryloxypropanolamine andrenergic antagonist. Used in the treatment of a variety of cardiovascular disorder.

Technology Process of Metoprolol

There total 8 articles about Metoprolol 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: 99.58%

isopropylamine (75-31-0) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → (RS)-metoprolol (51384-51-1,37350-58-6)

Guidance literature:

In ethanol; at 50 - 92 ℃; Temperature; Flow reactor;

Reference yield: 90.0%

→ (RS)-metoprolol (51384-51-1,37350-58-6)

Guidance literature:

Reference yield:

metoprolol tartrate → (RS)-metoprolol (51384-51-1,37350-58-6)

Guidance literature:

With Dowex Marathon 11 chloride form; In water;

DOI:10.1107/S2053229618017084

upstream raw materials:

3-[4-(2-methoxyethyl)phenoxy]propylene

isopropylamine

2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane

4-(2-methoxyethyl)phenol

Downstream raw materials:

metoprolol Succinate

metoprolol tartrate

N-(3-vinyloxycarbonylpropanoyl)metoprolol

N-(5-vinyloxycarbonylpentanoyl)metoprolol

Refernces

• 1、 Rossi, Patrizia,Paoli, Paola,Chelazzi, Laura,Conti, Luca,Bencini, Andrea. "The solid-state structure of the β-blocker metoprolol: a combined experimental and in silico investigation". . p. 87 - 96. Retrieved 2019/01/24.
• 2、 -. "Preparation method of metoprolol". Paragraph 0031; 0033; 0034; 0037; 0040. . Retrieved 2017/07/23.