4-phenyl-1-(2-phenylethyl)piperidin-4-yl acetate

• ChemBase ID: 1346
• Molecular Formular: C21H25NO2
• Molecular Mass: 323.4287
• Monoisotopic Mass: 323.18852905
• SMILES: O(C1(CCN(CC1)CCc1ccccc1)c1ccccc1)C(=O)C
• Canonical SMILES: CC(=O)OC1(CCN(CC1)CCc1ccccc1)c1ccccc1
• InChI: InChI=1S/C21H25NO2/c1-18(23)24-21(20-10-6-3-7-11-20)13-16-22(17-14-21)15-12-19-8-4-2-5-9-19/h2-11H,12-17H2,1H3
• InChIKey: BVURVTVDNWSNFN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-phenyl-1-(2-phenylethyl)piperidin-4-yl acetate
• IUPAC Traditional name: pepap
• Synonyms: PEPAP; 1-(2-Phenethyl)-4-phenyl-4-acetoxypiperidine; 1-phenethyl-4-phenyl-4-piperidinol acetate; DEA No. 9663; 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine

Database IDs

• CAS Number: 64-52-8
• PubChem SID: 160964806; 46505389
• PubChem CID: 60977

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.3082284
• LogD (pH = 7.4): 1.7766529
• Log P: 3.6107306
• Molar Refractivity: 96.7337 cm^3
• Polarizability: 38.003803 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.18
• LOG S: -4.74
• Solubility (Water): 5.92e-03 g/l

DETAILS

DrugBank - DB01562

• Drug Groups: illicit; experimental
• Description: 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine (PEPAP) is a synthetic analogue of meperidine. It is sold as a "synthetic heroin."
• Affected Organisms: Humans and other mammals
• References: Pritzker D, Kanungo A, Kilicarslan T, Tyndale RF, Sellers EM: Designer drugs that are potent inhibitors of CYP2D6. J Clin Psychopharmacol. 2002 Jun;22(3):330-2. [Pubmed]

REFERENCES

• Pritzker D, Kanungo A, Kilicarslan T, Tyndale RF, Sellers EM: Designer drugs that are potent inhibitors of CYP2D6. J Clin Psychopharmacol. 2002 Jun;22(3):330-2. Pubmed