62572-94-5

Basic information

• Product Name: O-Desmethyl Metoprolol
• Synonyms: (-4-[2-Hydroxy-3-(isopropylamino)propoxy]phenylethyl Alcohol;(-O-Demethylmetoprolol;4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-benzeneethanol;H 105/22;O-Desmethyl Metoprolol;SL 80-008;O-demethylmetoprolo;SL 80-0088
• CAS NO: 62572-94-5
• Molecular Formula: C14H23NO3
• Molecular Weight: 253.34
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 62572-94-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 70-720C
• Boiling Point: 424.6°C at 760 mmHg
• Flash Point: 210.6°C
• Appearance: /
• Density: 1.085g/cm³
• Vapor Pressure: 5.73E-08mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly, Sonicated), Methanol (Slightly)
• PKA: 13.88±0.20(Predicted)
• CAS DataBase Reference: O-Desmethyl Metoprolol(CAS DataBase Reference)
• NIST Chemistry Reference: O-Desmethyl Metoprolol(62572-94-5)
• EPA Substance Registry System: O-Desmethyl Metoprolol(62572-94-5)

Safety Data

• Hazardous Substances Data: 62572-94-5(Hazardous Substances Data)

Usage

Description

O-Desmethyl Metoprolol, also known as Metoprolol EP Impurity H, is the major active metabolite of the β1-adrenergic receptor blocker Metoprolol. It is formed by the metabolism of Metoprolol by the cytochrome P450 (CYP) isoform CYP2D6 in vivo and is characterized by its off-white solid appearance.

Uses

Used in Pharmaceutical Industry:
O-Desmethyl Metoprolol is used as an active metabolite for enhancing the therapeutic effects of Metoprolol. As a metabolite, it contributes to the overall pharmacological action of Metoprolol, which is primarily used to treat conditions such as hypertension, angina, and certain types of arrhythmias. The presence of O-Desmethyl Metoprolol can influence the drug's efficacy and duration of action, making it an important consideration in the development and optimization of Metoprolol-based treatments.
Additionally, O-Desmethyl Metoprolol may be used as a reference compound or impurity standard in the quality control and regulatory processes of Metoprolol drug formulations, ensuring the safety and efficacy of the medication.

InChI:InChI=1/C14H23NO3/c1-11(2)15-9-13(17)10-18-14-5-3-12(4-6-14)7-8-16/h3-6,11,13,15-17H,7-10H2,1-2H3

Upstream product

• 81024-43-3 (2R)-metoprolol 
• 51384-51-1 (RS)-metoprolol 
• 104857-48-9 1-[4-(2-hydroxyethyl)phenoxy]-2,3-epoxypropane 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 75-31-0 isopropylamine 
• 29122-68-7 (RS)-atenolol 
• 959279-50-6 C₂₀H₂₉NO₆ 
• 1312687-84-5 C₁₈H₂₇NO₅ 
• 297741-05-0 (S)-1-[4-(2-hydroxyethyl)phenoxy]-2,3-epoxypropane 

Downstream Products

• 947340-61-6 (5S)-2-(4-((3-isopropyl-2-phenyloxazolidin)-5-methoxy)phenyl)-4-ethanol 
• 1237781-36-0 C₁₆H₂₅NO₄ 
• 1312687-84-5 C₁₈H₂₇NO₅ 
• 104857-50-3 (5S)-5-(4-((2-cyclopropylmethoxy)ethyl)phenoxy)methyl-3-isopropyl-2-phenyloxazolidine 

Relevant articles and documents

Regioselectivity and enantioselectivity of metoprolol oxidation by two variants of cDNA-expressed P4502D6

Purpose. The oxidative metabolism of metoprolol was investigated in two human lymphoblastoma cell-lines transfected with variants of cDNA for cytochrome P4502D6. Methods. The regioselective and enantioselective features of the oxidations of deuterium-labeled pseudoracemic metoprolol were characterized by GC/MS analysis of the substrate and products. Results. There were significant differences between the two P4502D6 variants in the formation kinetics of O-demethylmetoprolol and α-hydroxymetoprolol. The h2D6-Val microsomes highly favored the formation of the O-demethylmetoprolol regioisomer 6.3:1 and 2.8:1, respectively from (R)-metoprolol-d0 and (S)-metoprolol-d2, while the corresponding ratios for h2D6v2 microsomes were much lower. For both variants, O-demethylmetoprolol formation favored the (R)-substrate 1.5 to 2-fold, while α-hydroxymetoprolol formation was non-enantioselective. Similar Km values of metoprolol oxidation, 10-20 μM, were observed for the two microsomal preparations. Conclusions. The regioselectivity, enantioselectivity, and Km values for the h2D6-Val microsomes resemble those observed for the native P4502D6 in human liver microsomes, whereas the h2D6v2 microsomes deviated remarkably in regioselectivity.

Preparation method and application of 1-[(4-hydroxyethyl) phenoxy]-3-(isopropylamino) propan-2-ol

The invention belongs to the technical field of medicine preparation, and mainly relates to a preparation method of a compound 1-[(4-hydroxyethyl) phenoxy]-3-(isopropylamino) propyl-2-ol and application of the compound in betalol hydrochloride and betalol

Highly chemoselective reduction of amides (primary, secondary, tertiary) to alcohols using SmI2/amine/H2O under mild conditions

Highly chemoselective direct reduction of primary, secondary, and tertiary amides to alcohols using SmI2/amine/H2O is reported. The reaction proceeds with C-N bond cleavage in the carbinolamine intermediate, shows excellent functional group tolerance, and delivers the alcohol products in very high yields. The expected C-O cleavage products are not formed under the reaction conditions. The observed reactivity is opposite to the electrophilicity of polar carbonyl groups resulting from the nX → πC=O (X = O, N) conjugation. Mechanistic studies suggest that coordination of Sm to the carbonyl and then to Lewis basic nitrogen in the tetrahedral intermediate facilitate electron transfer and control the selectivity of the C-N/C-O cleavage. Notably, the method provides direct access to acyl-type radicals from unactivated amides under mild electron transfer conditions.