4-[(1S,2R)-1-hydroxy-2-(methylamino)propyl]phenol

• ChemBase ID: 170203
• Molecular Formular: C10H15NO2
• Molecular Mass: 181.2316
• Monoisotopic Mass: 181.11027873
• SMILES: c1c(ccc(c1)[C@@H]([C@H](NC)C)O)O
• Canonical SMILES: CN[C@@H]([C@H](c1ccc(cc1)O)O)C
• InChI: InChI=1S/C10H15NO2/c1-7(11-2)10(13)8-3-5-9(12)6-4-8/h3-7,10-13H,1-2H3/t7-,10-/m1/s1
• InChIKey: OXFGTKPPFSCSMA-GMSGAONNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2R)-1-hydroxy-2-(methylamino)propyl]phenol
• IUPAC Traditional name: 4-[(1S,2R)-1-hydroxy-2-(methylamino)propyl]phenol
• Synonyms: (αS)-rel-4-Hydroxy-α-[(1R)-1-(methylamino)ethyl]benzenemethanol; p-hydroxy-α-[1-(methylamino)ethyl]benzyl Alcohol; (±)-Hydroxyephedrine; (±)-p-Hydroxyephedrine; 1-(4-Hydroxyphenyl)-1-hydroxy-2-methylaminopropane; 4-Hydroxyephedrine; Methylsympatol; Oxilofrine; Oxyephedrine; Suprifen; Supriphen; dl-p-Hydroxyephedrine; p-Hydroxyephedrine; rac 4-Hydroxy Ephedrine

Database IDs

• CAS Number: 365-26-4
• PubChem SID: 164226113
• PubChem CID: 688012

CALCULATED PROPERTIES

• Acid pKa: 9.19267
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -2.1565952
• LogD (pH = 7.4): -1.0539908
• Log P: 0.2835567
• Molar Refractivity: 51.6682 cm^3
• Polarizability: 20.436266 Å^3
• Polar Surface Area: 52.49 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H825305

4-Hydroxyephedrine is the 4-hydroxy analogue and a metabolite of the α- and β-adrenergic agonist Ephedrine (E575000).

REFERENCES

• Baba, S. et al. Yakug. Zas., 92, 1534 (1972)
• Niwaguchi, T. et al.: Kag. Keit. Ken. Hok. Hokag., 33, 216 (1972)
• Aoki, K. et al.: Forensic Sci. Int., 80, 163 (1972)