(5S,7S)-7-{[4-(2,6-dichlorophenyl)piperidin-1-yl]methyl}-1-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol hydrochloride

• ChemBase ID: 177639
• Molecular Formular: C24H30Cl3NO
• Molecular Mass: 454.8601
• Monoisotopic Mass: 453.13929763
• SMILES: c1ccc(c(c1Cl)C1CCN(CC1)C[C@H]1CCc2c([C@H](C1)O)cccc2C)Cl.Cl
• Canonical SMILES: O[C@H]1C[C@H](CCc2c1cccc2C)CN1CCC(CC1)c1c(Cl)cccc1Cl.Cl
• InChI: InChI=1S/C24H29Cl2NO.ClH/c1-16-4-2-5-20-19(16)9-8-17(14-23(20)28)15-27-12-10-18(11-13-27)24-21(25)6-3-7-22(24)26;/h2-7,17-18,23,28H,8-15H2,1H3;1H/t17-,23-;/m0./s1
• InChIKey: DCKUVQADDNMWEF-DQFHVVJASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S,7S)-7-{[4-(2,6-dichlorophenyl)piperidin-1-yl]methyl}-1-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol hydrochloride
• IUPAC Traditional name: (5S,7S)-7-{[4-(2,6-dichlorophenyl)piperidin-1-yl]methyl}-1-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol hydrochloride
• Synonyms: (5S,7S)-7-[[4-(2,6-Dichlorophenyl)-1-piperidinyl]methyl]-6,7,8,9-tetrahydro-1-methyl-5H-benzocyclohepten-5-ol Hydrochloride; (-)-cis-1-Methyl-7-[[4-(2,6-dichlorophenyl)piperidin-1-yl]methyl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol Hydrochloride; SB 612111 Hydrochloride

Database IDs

• PubChem SID: 164233549
• PubChem CID: 21061234

CALCULATED PROPERTIES

• Acid pKa: 14.501679
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.3336408
• LogD (pH = 7.4): 5.0702796
• Log P: 6.268998
• Molar Refractivity: 119.2202 cm^3
• Polarizability: 46.200165 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S154750

A selective nociceptin/orphanin FQ receptor antagonist. A potentially useful adjunct to chronic pain therapy with opioids and can be used to treat conditions in which thermal hyperalgesia is a significant component of the pain response.

REFERENCES

• Rizzi, A. et al.: J. Pharmacol. Exp. Therap., 321, 968 (2007)
• Liao, Y. et al.: Eur. J. Pharmacol., 657, 84 (2007)
• Zaratin. P.F. et al.: J. Pharmacol. Exp. Therap., 308, 454 (2007)