[(2S)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl](propan-2-yl)amine

• ChemBase ID: 174587
• Molecular Formular: C15H25NO3
• Molecular Mass: 267.3639
• Monoisotopic Mass: 267.18344367
• SMILES: CC(NC[C@@H](COc1ccc(cc1)CCOC)O)C
• Canonical SMILES: COCCc1ccc(cc1)OC[C@H](CNC(C)C)O
• InChI: InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3/t14-/m0/s1
• InChIKey: IUBSYMUCCVWXPE-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl](propan-2-yl)amine
• IUPAC Traditional name: [(2S)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl](isopropyl)amine
• Synonyms: (2S)-1-[4-(2-Methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-2-propanol; (-)-Metoprolol; (S)-(-)-Metoprolol; (S)-Metoprolol

Database IDs

• CAS Number: 81024-42-2
• PubChem SID: 164230497
• PubChem CID: 157716

CALCULATED PROPERTIES

• Acid pKa: 14.087972
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.4345746
• LogD (pH = 7.4): -0.46658155
• Log P: 1.7586571
• Molar Refractivity: 76.6976 cm^3
• Polarizability: 30.335455 Å^3
• Polar Surface Area: 50.72 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Light Beige Low Melting Solid
• Melting Point: 41-43°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M338780

(S)-Enantiomer of Metoprolol. Antihypertensive; antianginal; antiarrhythmic (class II).

REFERENCES

• Johansson, et al.: Eur. J. Pharmacol., 24, 194 (1973)
• Luch, J.R., et al.: Anal. Profiles Drug Subs., 12, 325 (1973)
• Benfield, P., et al.: Drugs, 31, 376 (1973)