4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N-methyl-2,2-diphenylbutanamide

• ChemBase ID: 166469
• Molecular Formular: C28H31ClN2O2
• Molecular Mass: 463.01094
• Monoisotopic Mass: 462.20740592
• SMILES: c1c(ccc(c1)C1(CCN(CC1)CCC(c1ccccc1)(c1ccccc1)C(=O)NC)O)Cl
• Canonical SMILES: CNC(=O)C(c1ccccc1)(c1ccccc1)CCN1CCC(CC1)(O)c1ccc(cc1)Cl
• InChI: InChI=1S/C28H31ClN2O2/c1-30-26(32)28(23-8-4-2-5-9-23,24-10-6-3-7-11-24)18-21-31-19-16-27(33,17-20-31)22-12-14-25(29)15-13-22/h2-15,33H,16-21H2,1H3,(H,30,32)
• InChIKey: ZMOPTLXEYOVARP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N-methyl-2,2-diphenylbutanamide
• IUPAC Traditional name: desmethyl loperamide
• Synonyms: 4-(4-Chlorophenyl)-4-hydroxy-N-methyl-α,α-diphenyl-1-piperidinebutanamide; R 20905; N-Desmethyl Loperamide

Database IDs

• CAS Number: 66164-07-6
• PubChem SID: 162260602
• PubChem CID: 9805944

CALCULATED PROPERTIES

• Acid pKa: 13.956883
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.1843525
• LogD (pH = 7.4): 2.530363
• Log P: 4.547515
• Molar Refractivity: 134.4223 cm^3
• Polarizability: 52.41886 Å^3
• Polar Surface Area: 52.57 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 219-221°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D291840

A metabolite of Loperamide; a new and improved PET radiotracer for imaging P-gp function.

REFERENCES

• Rahman, A., et al.: Cancer Res., 54, 5543 (1994)
• Sai, Y., et al.: Xenobiotica, 30, 327 (1994)
• Eneroth, A., et al.: Eur. J. Pharm. Sci., 12, 205 (1994)
• Kim, K., et al.: Drug Metab. Dispos., 31, 1090 (1994)
• Kannan et al. Drug Metab. Dispos., 38, 917 (2