1-(3-amino-1-phenylpropoxy)-4-(trifluoromethyl)benzene

• ChemBase ID: 4462
• Molecular Formular: C16H16F3NO
• Molecular Mass: 295.2995496
• Monoisotopic Mass: 295.1183988
• SMILES: FC(F)(F)c1ccc(OC(CCN)c2ccccc2)cc1
• Canonical SMILES: NCCC(c1ccccc1)Oc1ccc(cc1)C(F)(F)F
• InChI: InChI=1S/C16H16F3NO/c17-16(18,19)13-6-8-14(9-7-13)21-15(10-11-20)12-4-2-1-3-5-12/h1-9,15H,10-11,20H2
• InChIKey: WIQRCHMSJFFONW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(3-amino-1-phenylpropoxy)-4-(trifluoromethyl)benzene
• IUPAC Traditional name: 1-(3-amino-1-phenylpropoxy)-4-(trifluoromethyl)benzene; seproxetine
• Synonyms: (S)-norfluoxetine; Seproxetine HCL; Seproxetine hydrochloride; Seproxetine hydrochloride (usan); Seproxetine hydrochloride [usan]; UNII-K4QYN23H2N; Seproxetine; Norfluoxetine

Database IDs

• CAS Number: 126924-38-7; 83891-03-6
• PubChem SID: 99443277; 160967894
• PubChem CID: 4541

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.7320839
• LogD (pH = 7.4): 1.4558952
• Log P: 3.7406392
• Molar Refractivity: 75.5929 cm^3
• Polarizability: 28.61059 Å^3
• Polar Surface Area: 35.25 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.8
• LOG S: -4.51
• Solubility (Water): 9.15e-03 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Light Brown Solid
• Melting Point: 105-108°C

Safety Information

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

DETAILS

DrugBank - DB06731

• Drug Groups: investigational
• Description: Seproxetine, also known as (S)-norfluoxetine, is a selective serotonin reuptake inhibitor (SSRI). It is an active metabolite of fluoxetine. Seproxetine was being investigated by Eli Lilly as an antidepressant but development was never completed and the drug was never marketed.
• Half Life: 4-16 days
• External Links: Wikipedia

Toronto Research Chemicals - N681100

A metabolite of Fluoxetine (F597100), a selective serotonin reuptake inhibitor which is used as an antidepressant.

REFERENCES

• Wong, D., et al.: J. Pharmacol. Exp. Ther., 193, 804 (1975)
• Thorsen, T., et al.: J. Cancer Clin. Oncol., 18, 333 (1975)
• Howell, A., et al.: Lancet, 365, 60 (1975)