O-Desmethyl Metoprolol Chemical Properties

Melting point:

70-720C

Boiling point:

424.6±40.0 °C(Predicted)

Density 

1.085±0.06 g/cm3(Predicted)

storage temp. 

-20°C Freezer

solubility 

Chloroform (Slightly, Sonicated), Methanol (Slightly)

form 

Solid

pka

13.88±0.20(Predicted)

color 

White to Off-White

InChI

InChI=1S/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

InChIKey

CUKXSBOAIJILRY-UHFFFAOYSA-N

SMILES

C1(CCO)=CC=C(OCC(O)CNC(C)C)C=C1

Safety Information

Toxicity

LD50 intravenous in dog: 150mg/kg

O-Desmethyl Metoprolol Usage And Synthesis

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.

Chemical Properties

Off-White Solid

Uses

O-Desmethyl Metoprolol (Metoprolol EP Impurity H) is a metabolite of Metoprolol.

References

[1] PAULA MACEDO CERQUEIRA. Stereoselective metabolism of metoprolol: Enantioselectivity of α-hydroxymetoprolol in plasma and urine[J]. Chirality, 2003, 15 6: 542-549. DOI: 10.1002/chir.10244
[2] ANGELA SEERINGER. Enantiospecific pharmacokinetics of metoprolol in CYP2D6 ultra-rapid metabolizers and correlation with exercise-induced heart rate.[J]. European Journal of Clinical Pharmacology, 2008, 64 9: 883-888. DOI: 10.1007/s00228-008-0504-8
[3] SOO HYEON BAE. Simultaneous determination of metoprolol and its metabolites, α-hydroxymetoprolol and O-desmethylmetoprolol, in human plasma by liquid chromatography with tandem mass spectrometry: Application to the pharmacokinetics of metoprolol associated with CYP2D6 genotypes[J]. Journal of separation science, 2014, 37 11: 1256-1264. DOI: 10.1002/jssc.201301353

O-Desmethyl Metoprolol(62572-94-5)Related Product Information

• 3-[2-Hydroxy-3-[4-(2-methoxyethyl)phenoxy]propoxy]-1-isopropylamino-2-propanol
• 1-(2-methoxyethyl)-4-nitrobenzene
• 3-(ISOPROPYLAMINO)-1,2-PROPANEDIOL
• H 128/80
• rac 1-Chloro-3-[4-(2-methoxyethyl)phenoxy]-2-propanol
• 1,3-Bis[(1-Methylethyl)aMino]-2-propanol Dihydrochloride
• 1-(isopropylamino)-3-phenoxy-2-propanol
• 3-[4-(2-Methoxyethyl)phenoxy]-
• 2-Propanol, 1-[2-(2-methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-
• p-(2-Methoxyethyl) phenol
• 1,1′-[(1-Methylethyl)imino]bis[3-[4-(2-methoxyethyl)phenoxy]-2-propanol hydrochloride
• C-Desmethyl Metoprolol
• 4-Hydroxyphenethyl alcohol
• Metoprolol Impurity 1
• Metoprolol EP IMpurity M
• 1-[4-(2-Methoxyethenyl)phenoxy]-3-[(1-Methylethyl)aMino]-2-propanol
• 1,1[(1-Methylethyl)imino]bis[3-[4-(2-methoxyethyl)phenoxy]-2-propanol(Mixture of diastereomers)
• LEVOBETAXOLOL