(2R,3S)-2,3-dihydroxybutanedioic acid; {2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl}(propan-2-yl)amine

• ChemBase ID: 174591
• Molecular Formular: C19H31NO9
• Molecular Mass: 417.45074
• Monoisotopic Mass: 417.19988158
• SMILES: CC(NCC(COc1ccc(cc1)CCOC)O)C.[C@@H]([C@@H](C(=O)O)O)(C(=O)O)O
• Canonical SMILES: OC(=O)[C@H]([C@H](C(=O)O)O)O.COCCc1ccc(cc1)OCC(CNC(C)C)O
• InChI: InChI=1S/C15H25NO3.C4H6O6/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3;5-1(3(7)8)2(6)4(9)10/h4-7,12,14,16-17H,8-11H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2+
• InChIKey: WPTKISQJQVFSQI-YKWZRPGSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2,3-dihydroxybutanedioic acid; {2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl}(propan-2-yl)amine
• IUPAC Traditional name: (-)-tartaric acid; metoprolol
• Synonyms: 1-[4-(2-Methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-2-propanol Hemi (+)-Tartrate; Beloc; Betaloc; Lapressor; Prelis; Seloken; Selopral; rac Metoprolol Hemi (+)-Tartrate

Database IDs

• CAS Number: 56392-17-7
• PubChem SID: 164230501
• PubChem CID: 16219665

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: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Crystalline Powder

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M338790

A β1 selective aryloxypropanolamine andrenergic antagonist. Used in the treatment of a variety of cardiovascular disorder.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)