N-[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylacetamide

• ChemBase ID: 159265
• Molecular Formular: C12H17NO2
• Molecular Mass: 207.26888
• Monoisotopic Mass: 207.12592879
• SMILES: c1cccc(c1)[C@@H]([C@H](N(C(=O)C)C)C)O
• Canonical SMILES: O[C@H]([C@H](N(C(=O)C)C)C)c1ccccc1
• InChI: InChI=1S/C12H17NO2/c1-9(13(3)10(2)14)12(15)11-7-5-4-6-8-11/h4-9,12,15H,1-3H3/t9-,12-/m1/s1
• InChIKey: ZZGMTCKULVMTDB-BXKDBHETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylacetamide
• IUPAC Traditional name: N-[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylacetamide
• Synonyms: (R*,S*)-N-(2-Hydroxy-1-methyl-2-phenylethyl)-N-methylacetamide; erythro-N-(β-Hydroxy-α-methylphenethyl)-N-methylacetamide; N-Acetylephedrine; rac N-Acetyl Ephedrine

Database IDs

• CAS Number: 5661-42-7
• PubChem SID: 162253400
• PubChem CID: 71160408

CALCULATED PROPERTIES

• Acid pKa: 13.86342
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.9277767
• LogD (pH = 7.4): 0.9277769
• Log P: 0.927777
• Molar Refractivity: 59.2532 cm^3
• Polarizability: 23.197641 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A173850

An acetylated derivative of the α- and β-Adrenergic agonist Ephedrine (E575000).

REFERENCES

• Coutts, R.T. et al.: Biomed. Mass Spec., 11, 441 (1984)