(1S,2R)-1-(3-chlorophenyl)-2-{[2-(2H3)methyl(2H6)propan-2-yl]amino}propan-1-ol

• ChemBase ID: 167379
• Molecular Formular: C13H20ClNO
• Molecular Mass: 241.757
• Monoisotopic Mass: 241.12334195
• SMILES: c1cc(cc(c1)[C@@H]([C@H](NC(C)(C)C)C)O)Cl
• Canonical SMILES: C[C@H]([C@H](c1cccc(c1)Cl)O)NC(C)(C)C
• InChI: InChI=1S/C13H20ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,12,15-16H,1-4H3/t9-,12-/m1/s1
• InChIKey: NDPTTXIBLSWNSF-BXKDBHETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R)-1-(3-chlorophenyl)-2-{[2-(^2H₃)methyl(^2H₆)propan-2-yl]amino}propan-1-ol
• IUPAC Traditional name: (1S,2R)-1-(3-chlorophenyl)-2-{[2-(^2H₃)methyl(^2H₆)propan-2-yl]amino}propan-1-ol
• Synonyms: (αS)-rel-3-Chloro-α-[(1R)-1-[(1,1-dimethylethyl)amino]ethyl]benzenemethanol-d9; rac erythro-Hydroxybupropion-d9; rac erythro-Dihydro Bupropion-d9

Database IDs

• PubChem SID: 162261512
• PubChem CID: 45039021

CALCULATED PROPERTIES

• Acid pKa: 13.8068695
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.22224288
• LogD (pH = 7.4): 0.70772356
• Log P: 2.9758391
• Molar Refractivity: 68.2977 cm^3
• Polarizability: 27.219843 Å^3
• Polar Surface Area: 32.26 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Off-White Solid
• Melting Point: 55-58°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D448652

A labelled metabolite of the drug Bupropion (B689625).

REFERENCES

• Hsyu, P-H., et al.: J. Clin. Pharmacol., 37, 737 (1997)