N-phenyl-4-(quinolin-3-ylmethyl)piperidine-1-carboxamide

• ChemBase ID: 154449
• Molecular Formular: C22H23N3O
• Molecular Mass: 345.43752
• Monoisotopic Mass: 345.18411237
• SMILES: c1ccc(cc1)NC(=O)N1CCC(CC1)Cc1cc2ccccc2nc1
• Canonical SMILES: O=C(N1CCC(CC1)Cc1cnc2c(c1)cccc2)Nc1ccccc1
• InChI: InChI=1S/C22H23N3O/c26-22(24-20-7-2-1-3-8-20)25-12-10-17(11-13-25)14-18-15-19-6-4-5-9-21(19)23-16-18/h1-9,15-17H,10-14H2,(H,24,26)
• InChIKey: BIODYGOZWZNCAG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-phenyl-4-(quinolin-3-ylmethyl)piperidine-1-carboxamide
• IUPAC Traditional name: N-phenyl-4-(quinolin-3-ylmethyl)piperidine-1-carboxamide
• Synonyms: N-Phenyl-4-(3-quinolinylmethyl)-1-piperidinecarboxamide; PF 750; N-Phenyl-4-(quinolin-3-ylmethyl)piperidine-1-carboxamide; PF-750

Database IDs

• CAS Number: 959151-50-9
• MDL Number: MFCD10567109
• PubChem SID: 162248588
• PubChem CID: 25154868

CALCULATED PROPERTIES

• Acid pKa: 13.424739
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.116559
• LogD (pH = 7.4): 4.197035
• Log P: 4.1981754
• Molar Refractivity: 104.699 cm^3
• Polarizability: 41.004833 Å^3
• Polar Surface Area: 45.23 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H23N3O

DETAILS

Sigma Aldrich - P0041

Biochem/physiol Actions
PF-750 is a potent, time-dependent, irreversible FAAH inhibitor with IC50 values 0.6 and 0.016 μM when preincubated with recombinant human FAAH for 5 and 60 minutes, respectively. Fatty acid amide hydrolase (FAAH) is the enzyme responsible for hydrolysis and inactivation of fatty acid amides including anandamide and oleamide. Activity-based profiling of various human and murine tissue proteome samples revealed that PF-750 is highly selective for FAAH relative to other serine hydrolases, showing no discernable off-site activity up to 500 μM. PF-750 shows 10-fold better potency than URB597 (Sigma# U4133) after 30 min preincubation. PF-750 is highly selective on FAAH. Even at as high as 500 μM, it had no interactions with many tested enzymes, but URB597 and other known FAAH inhibitors did not perform well at low concentraction (100 μM).

Toronto Research Chemicals - P293800

Fatty acid amide hydrolase (FAAH) inhibitor, selectively inhibiting FAAH within the central nervous system

REFERENCES

• Ahn, K., et al.: Biochem., 46, 13019 (2007)
• Mileni, M., et al.: Proc. Natl. Acad. Sci. USA., 105, 12820 (2007)