4-[(1S)-3-(methylamino)-1-(thiophen-2-yl)propoxy]naphthalen-1-ol

• ChemBase ID: 170422
• Molecular Formular: C18H19NO2S
• Molecular Mass: 313.41396
• Monoisotopic Mass: 313.11364985
• SMILES: c1(ccc(c2c1cccc2)O)O[C@H](c1sccc1)CCNC
• Canonical SMILES: CNCC[C@@H](c1cccs1)Oc1ccc(c2c1cccc2)O
• InChI: InChI=1S/C18H19NO2S/c1-19-11-10-17(18-7-4-12-22-18)21-16-9-8-15(20)13-5-2-3-6-14(13)16/h2-9,12,17,19-20H,10-11H2,1H3/t17-/m0/s1
• InChIKey: DRRXQCXSBONKPD-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S)-3-(methylamino)-1-(thiophen-2-yl)propoxy]naphthalen-1-ol
• IUPAC Traditional name: 4-[(1S)-3-(methylamino)-1-(thiophen-2-yl)propoxy]naphthalen-1-ol
• Synonyms: 4-[(1S)-3-(Methylamino)-1-(2-thienyl)propoxy]-1-naphthalenol; 4-Hydroxy Duloxetine

Database IDs

• CAS Number: 662149-13-5
• PubChem SID: 164226332
• PubChem CID: 29981497

CALCULATED PROPERTIES

• Acid pKa: 9.305142
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.70141953
• LogD (pH = 7.4): 1.6703532
• Log P: 3.1658998
• Molar Refractivity: 89.7148 cm^3
• Polarizability: 36.273987 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO; Methanol
• Apperance: Tan Solid
• Melting Point: >135°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H941800

A major metabolite of Duloxetine.

REFERENCES

• Lantz, R.J., et al.: Drug Dispos. Metab., 31, 1142 (2003)
• Detke, M., et al.: J. Clin Psy., 63, 308 (2003)
• Bymaster, F.P., et al.: Bioorg. Med., Chem. Lett., 13, 4477 (2003)