1-[(1S)-2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol

• ChemBase ID: 179480
• Molecular Formular: C17H27NO2
• Molecular Mass: 277.40178
• Monoisotopic Mass: 277.20417911
• SMILES: c1cc(ccc1[C@H](C1(CCCCC1)O)CN(C)C)OC
• Canonical SMILES: COc1ccc(cc1)[C@H](C1(O)CCCCC1)CN(C)C
• InChI: InChI=1S/C17H27NO2/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14/h7-10,16,19H,4-6,11-13H2,1-3H3/t16-/m1/s1
• InChIKey: PNVNVHUZROJLTJ-MRXNPFEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S)-2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol
• IUPAC Traditional name: 1-[(1S)-2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol
• Synonyms: 1-[(1S)-2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol; (-)-Venlafaxine; S-Venlafaxine

Database IDs

• CAS Number: 93413-44-6
• PubChem SID: 164235390
• PubChem CID: 11846746

CALCULATED PROPERTIES

• Acid pKa: 14.420212
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.412785
• LogD (pH = 7.4): 1.221672
• Log P: 2.7385228
• Molar Refractivity: 83.0242 cm^3
• Polarizability: 32.606743 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 102-104°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - V120008

A optically active version of Venlafaxine, a selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant.

REFERENCES

• Jones, G., et al.: J. Mol. Biol., 267, 727 (1997)
• Bissantz, C., et al.: J. Med. Chem., 43, 4759 (1997)
• Hou, T., et al.: Curr. Pharm. Des., 10, 1011 (1997)
• Kellenberger, E., et al.: Proteins, 57, 225 (1997)