(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol

• ChemBase ID: 170125
• Molecular Formular: C13H18ClNO2
• Molecular Mass: 255.74052
• Monoisotopic Mass: 255.1026065
• SMILES: C1(N[C@H]([C@](OC1)(O)c1cc(ccc1)Cl)C)(C)C
• Canonical SMILES: Clc1cccc(c1)[C@]1(O)OCC(N[C@H]1C)(C)C
• InChI: InChI=1S/C13H18ClNO2/c1-9-13(16,17-8-12(2,3)15-9)10-5-4-6-11(14)7-10/h4-7,9,15-16H,8H2,1-3H3/t9-,13+/m0/s1
• InChIKey: RCOBKSKAZMVBHT-TVQRCGJNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol
• IUPAC Traditional name: radafaxine
• Synonyms: (2S,3S)-2-(3-Chlorophenyl)-3,5,5-trimethyl-2-morpholinol; Radafaxine; (2S-cis)-2-(3-Chlorophenyl)-3,5,5-trimethyl-2-morpholinol; (+)-(2S,3S)-2-(3-Chlorophenyl)-3,5,5-trimethyl-2-morpholinol; GW 353162; (S,S)-Hydroxy Bupropion

Database IDs

• CAS Number: 192374-14-4
• PubChem SID: 164226035
• PubChem CID: 9795056

CALCULATED PROPERTIES

• Acid pKa: 10.754683
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.81730276
• LogD (pH = 7.4): 2.479874
• Log P: 2.9009485
• Molar Refractivity: 67.7986 cm^3
• Polarizability: 27.185991 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Light Beige Solid
• Melting Point: 121-123°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H830670

(S,S) Enantiomer metabolite of Bupropion (B689625), an antidepressant.

REFERENCES

• Hsyu, P-H., et al.: J. Clin. Pharm., 37, 737 (1997)
• Rotzinger, S., et al.: Cellular & Mol. Neurobiology, 19, 4, 427 (1997)
• US 6342496