(2-{4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy}ethyl)diethylamine hydrochloride

• ChemBase ID: 164817
• Molecular Formular: C26H29Cl2NO
• Molecular Mass: 442.42056
• Monoisotopic Mass: 441.16261991
• SMILES: c1cc(ccc1/C(=C(\c1ccccc1)/Cl)/c1ccccc1)OCCN(CC)CC.Cl
• Canonical SMILES: CCN(CCOc1ccc(cc1)/C(=C(\c1ccccc1)/Cl)/c1ccccc1)CC.Cl
• InChI: InChI=1S/C26H28ClNO.ClH/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23;/h5-18H,3-4,19-20H2,1-2H3;1H/b26-25+
• InChIKey: KKBZGZWPJGOGJF-BTKVJIOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy}ethyl)diethylamine hydrochloride
• IUPAC Traditional name: clomifene hydrochloride
• Synonyms: (E)-2-[p-(2-chloro-1,2-diphenylvinyl)phenoxy]-triethylamine Hydrochloride; 2-[4-[(1E)-2-Chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethyl-ethanamine Hydrochloride; (E)-Clomiphene Hydrochloide; ICI 46476; Enclomifene Hydrochloride; Enclomiphene Hydrochloride; trans-Clomifene Hydrochloride; trans-Clomiphene Hydrochloride

Database IDs

• CAS Number: 14158-65-7
• PubChem SID: 162258951
• PubChem CID: 71314885

CALCULATED PROPERTIES

• Log P: 6.474938
• Molar Refractivity: 133.7612 cm^3
• Polarizability: 48.233112 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.1481478
• LogD (pH = 7.4): 4.573795

DETAILS

Toronto Research Chemicals - C587035

Trans isomer of Clomiphene (C587025). Found to be slightly estrogenic and a less potent inhibitor of LH secretion than the cis isomer.

REFERENCES

• Robert, B.S.: J. Anim. Sci., 33, 607 (1971)
• Weissenberg, R.: Andrologia, 24, 162 (1971)
• Palopoli, F.P., J. Med. Chem., 10, 84 (1971)
• Ernst., et al.: J. Pharm. Sci., 65, 148 (1971)
• Baustian, C.L., et al.: Pharm. Biomed. Anal., 4, 237 (1971)