O-Demethylmetoprolol

Base Information

• Chemical Name: O-Demethylmetoprolol
• CAS No.: 62572-94-5
• Molecular Formula: C₁₄H₂₃NO₃
• Molecular Weight: 253.342
• European Community (EC) Number: 641-522-4
• UNII: 9977TAV7FG
• DSSTox Substance ID: DTXSID40978153
• Nikkaji Number: J440.346K
• Wikidata: Q27272183
• ChEMBL ID: CHEMBL3544687
• Mol file: 62572-94-5.mol

Synonyms:H 105-22;H105-22;H105-22, (+-)-isomer;O-demethylmetoprolol

Chemical Property of O-Demethylmetoprolol

Chemical Property:

• Vapor Pressure: 5.73E-08mmHg at 25°C
• Melting Point: 70-72oC
• Boiling Point: 424.6°C at 760 mmHg
• PKA: 13.88±0.20(Predicted)
• Flash Point: 210.6°C
• PSA: 61.72000
• Density: 1.085g/cm³
• LogP: 1.35000
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 253.16779360
• Heavy Atom Count: 18
• Complexity: 203

Purity/Quality:

NLT 98% ^*data from raw suppliers

O-Desmethyl Metoprolol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=C(C=C1)CCO)O
• Description: O-Desmethyl metoprolol is the major active metabolite of the β1-adrenergic receptor blocker metoprolol . It is formed by metabolism of metoprolol by the cytochrome P450 (CYP) isoform CYP2D6 in vivo.
• Uses: A metabolite of Metoprolol O-Desmethyl Metoprolol (Metoprolol EP Impurity H) is a metabolite of Metoprolol.

Technology Process of O-Demethylmetoprolol

There total 14 articles about O-Demethylmetoprolol 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: 98.0%

C18H27NO5 (1312687-84-5) → (-)-O-Demethylmetoprolol (131564-69-7,62572-94-5)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃;

DOI:10.1080/00397911.2010.505699

Reference yield: 61.0%

(RS)-atenolol (29122-68-7) → (+/-)-O-Demethylmetoprolol (62572-94-5)

Guidance literature:

With samarium diiodide; water; triethylamine; In tetrahydrofuran; at 23 ℃; for 18h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/ja412578t

Reference yield:

(RS)-metoprolol (51384-51-1,37350-58-6) → alpha-Hydroxymetoprolol (56392-16-6) + (+/-)-O-Demethylmetoprolol (62572-94-5)

Guidance literature:

With CYP₂D_6.1; NADPH; In phosphate buffer; pH=7.4; Further Variations:; Reagents; Enzyme kinetics;

DOI:10.1016/S0006-2952(02)01351-5

upstream raw materials:

(2R)-metoprolol

(RS)-metoprolol

1-[4-(2-hydroxyethyl)phenoxy]-2,3-epoxypropane

p-hydroxyphenethyl alcohol

Downstream raw materials:

(5S)-2-(4-((3-isopropyl-2-phenyloxazolidin)-5-methoxy)phenyl)-4-ethanol

C₁₆H₂₅NO₄

C₁₈H₂₇NO₅

(5S)-5-(4-((2-cyclopropylmethoxy)ethyl)phenoxy)methyl-3-isopropyl-2-phenyloxazolidine

Refernces

• 1、 -. "Preparation method and application of 1-[(4-hydroxyethyl) phenoxy]-3-(isopropylamino) propan-2-ol". Paragraph 0019; 0021-0024. . Retrieved 2020/10/04.
• 2、 -. "Technique for synthesizing levorotatory betaxolol hydrochloride (by machine translation)". . . Retrieved 2017/03/17.