(1R,2R)-2-(4-phenylpiperidin-1-yl)cyclohexan-1-ol

• ChemBase ID: 179866
• Molecular Formular: C17H25NO
• Molecular Mass: 259.3865
• Monoisotopic Mass: 259.19361443
• SMILES: N1([C@H]2[C@H](O)CCCC2)CCC(CC1)c1ccccc1
• Canonical SMILES: O[C@@H]1CCCC[C@H]1N1CCC(CC1)c1ccccc1
• InChI: InChI=1S/C17H25NO/c19-17-9-5-4-8-16(17)18-12-10-15(11-13-18)14-6-2-1-3-7-14/h1-3,6-7,15-17,19H,4-5,8-13H2/t16-,17-/m1/s1
• InChIKey: YSSBJODGIYRAMI-IAGOWNOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R)-2-(4-phenylpiperidin-1-yl)cyclohexan-1-ol
• IUPAC Traditional name: (1R,2R)-2-(4-phenylpiperidin-1-yl)cyclohexan-1-ol
• Synonyms: Vesamicol

Database IDs

• CAS Number: 22232-64-0
• PubChem SID: 164235776
• PubChem CID: 659840

CALCULATED PROPERTIES

• Acid pKa: 14.596863
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.2674812
• LogD (pH = 7.4): 0.69691294
• Log P: 3.1857257
• Molar Refractivity: 79.1494 cm^3
• Polarizability: 31.223616 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Can be broadly categorized as a cholinergic physiological antagonist, because it reduces the apparent activity of cholinergic neurons, but does not act at the post-synaptic ACh receptor.; Causes a non-competitive and reversible block of the intracellular transporter responsible for carrying newly synthesised ACh into storage vesicles in the pre-synaptic nerve terminal.; Potent non-competitive inhibitor of acetylcholine storage.; Sympatholytic-alpha.; This transport process is driven by a proton gradient between cell organelles and the cytoplasm.

Product Information

• Application(s): Skeletal muscle relaxant

REFERENCES

• Kirkland, K.M. et al., J. Chromatogr., 1991, 545, 43, (hplc)
• Prior, C. et al., Gen. Pharmacol., 1992, 23, 1017, (rev)
• Enfange, S.M.N. et al., J. Med. Chem., 1994, 37, 2574, (sar)
• Parsons, S.M. et al., Ann. N.Y. Acad. Sci., 1987, 493, 220, (rev)
• Rogers, G.A. et al., Cell. Mol. Basis Cholinergic Funct., 1987, 333, (rev)
• Marien, M.R. et al., Proc. Natl. Acad. Sci. U.S.A., 1987, 84, 876
• Marshall, I.G. et al., Trends Neurosci., 1987, 10, 174, (rev)
• Estrella, D. et al., Br. J. Pharmacol., 1988, 93, 759, (pharmacol)
• Rogers, G.A. et al., J. Med. Chem., 1989, 32, 1217, (synth, props, cryst struct, sar)