CAS 62572-94-5

O-Demethylmetoprolol

Description:

O-Demethylmetoprolol, with the CAS number 62572-94-5, is a chemical compound that is a derivative of metoprolol, a well-known beta-blocker used primarily in the treatment of cardiovascular conditions such as hypertension and arrhythmias. This compound features a modified structure where a methoxy group is removed, resulting in altered pharmacological properties compared to its parent compound. O-Demethylmetoprolol is characterized by its ability to interact with beta-adrenergic receptors, although its affinity and efficacy may differ from metoprolol. The compound is typically a white to off-white solid, soluble in organic solvents, and has a moderate molecular weight. Its chemical structure includes a phenolic ring and an aliphatic side chain, which contribute to its biological activity. As a metabolite of metoprolol, O-Demethylmetoprolol may play a role in the drug's overall pharmacokinetics and pharmacodynamics, influencing therapeutic outcomes and side effects in patients. Further studies are often conducted to understand its specific biological effects and potential clinical significance.

Formula: C₁₄H₂₃NO₃

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

InChI key: InChIKey=CUKXSBOAIJILRY-UHFFFAOYSA-N

SMILES: O(CC(CNC(C)C)O)C1=CC=C(CCO)C=C1

Synonyms:

• (±)-4-[2-Hydroxy-3-(isopropylamino)propoxy]phenylethyl alcohol
• (±)-O-Demethylmetoprolol
• 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneethanol
• Benzeneethanol, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-
• H 105/22
• O-Desmethyl Metoprolol
• O-Desmethylmetoprolol
• Sl 80-0088

O-Desmethylmetoprolol (1-(4-(2-hydroxyethyl)phenoxy)-3-(isopropylamino)propan-2-ol)

CAS: 62572-94-5

Amino-alcohols, other than those containing more than one kind of oxygen function, their ethers and esters, salts thereof, nesoi

Formula: C₁₄H₂₃NO₃

Color and Shape: White Off-White Solid

Molecular weight: 253.16779

Ref: 45-1A03310

Metoprolol EP Impurity H (Betaxolol EP Impurity B)

CAS: 62572-94-5

Formula: C₁₄H₂₃NO₃

Color and Shape: White To Off-White Solid

Molecular weight: 253.34

Ref: 4Z-M-0812

(2RS)-1-[4-(2-Hydroxyethyl)phenoxy]-3-[(1-methylethyl)amino]propan-2-ol

Controlled Product

CAS: 62572-94-5

Formula: C₁₄H₂₃NO₃

Color and Shape: Neat

Molecular weight: 253.34

Ref: 86-MM0027.10

Betaxolol EP Impurity B

CAS: 62572-94-5

Formula: C₁₄H₂₃NO₃

Molecular weight: 253.34

Ref: ST-EA-CP-B33002

O-Desmethyl Metoprolol

Controlled Product

CAS: 62572-94-5

Impurity Metoprolol EP Impurity H / Betaxolol EP Impurity B
Applications O-Desmethyl Metoprolol (Metoprolol EP Impurity H) is a metabolite of Metoprolol.
References Lennard, M.S., et al.: Br. J. Clin. Pharmacol., 14, 713 (1982), Gengo, F.M., et al.: Clin. Pharmacol. Ther., 36, 320 (1984),

Formula: C₁₄H₂₃NO₃

Color and Shape: White To Off-White

Molecular weight: 253.34

Ref: TR-D292073

Metoprolol EP Impurity H

CAS: 62572-94-5

Formula: C₁₄H₂₃NO₃

Molecular weight: 253.34

Ref: ST-EA-CP-M17008

O-Desmethyl Metoprolol

CAS: 62572-94-5

O-Desmethyl metoprolol, a metabolite of metoprolol, acts as a β1-adrenergic receptor (β1-AR) antagonist. This compound is produced through the metabolism of metoprolol by the cytochrome P450 (CYP) isoform CYP2D6.

Formula: C₁₄H₂₃NO₃

Color and Shape: Solid

Molecular weight: 253.342

Ref: TM-T85293

O-Desmethyl metoprolol

CAS: 62572-94-5

O-Desmethyl metoprolol is an active metabolite of metoprolol. It has an inhibitory effect on beta-adrenergic receptors and acts as a vasodilator. O-Desmethyl metoprolol is formed by the action of cytochrome P450 on the parent drug, which has a strong acidic nature and is easily soluble in water. This metabolite can be detected in urine samples using a chromatographic method with detection sensitivity of 1 ng/mL. The stereoselectivity of the parent drug and its active metabolite is different, with the former being more selective for beta1 receptors while the latter is more selective for beta2 receptors. O-Desmethyl metoprolol may have clinical relevance because it was found to decrease blood pressure in hypertensive patients when given at doses that are much lower than those needed for its parent drug. The concentration of this metabolite in plasma was found to be proportional to dosage level and kinetic data suggest

Formula: C₁₄H₂₃NO₃

Purity: Min. 95%

Molecular weight: 253.34 g/mol

Ref: 3D-FD21293