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Identification
Name1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine
Accession NumberDB01562
TypeSmall Molecule
GroupsExperimental, Illicit
Description

1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine (PEPAP) is a synthetic analogue of meperidine. It is sold as a “synthetic heroin.”

Structure
Thumb
Synonyms
SynonymLanguageCode
1-(2-Phenethyl)-4-phenyl-4-acetoxypiperidineNot AvailableNot Available
1-phenethyl-4-phenyl-4-piperidinol acetateNot AvailableNot Available
PEPAPNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number64-52-8
WeightAverage: 323.4287
Monoisotopic: 323.188529049
Chemical FormulaC21H25NO2
InChI KeyBVURVTVDNWSNFN-UHFFFAOYSA-N
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
IUPAC Name
4-phenyl-1-(2-phenylethyl)piperidin-4-yl acetate
SMILES
CC(=O)OC1(CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassPhenylpiperidines
Direct ParentPhenylpiperidines
Alternative Parents
Substituents
  • Phenylpiperidine
  • Benzyloxycarbonyl
  • Phenethylamine
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Acetate salt
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.988
Blood Brain Barrier+0.9787
Caco-2 permeable+0.6548
P-glycoprotein substrateSubstrate0.6775
P-glycoprotein inhibitor IInhibitor0.8302
P-glycoprotein inhibitor IIInhibitor0.5604
Renal organic cation transporterInhibitor0.7384
CYP450 2C9 substrateNon-substrate0.8006
CYP450 2D6 substrateNon-substrate0.7419
CYP450 3A4 substrateSubstrate0.6116
CYP450 1A2 substrateNon-inhibitor0.8011
CYP450 2C9 substrateNon-inhibitor0.803
CYP450 2D6 substrateInhibitor0.7905
CYP450 2C19 substrateNon-inhibitor0.8544
CYP450 3A4 substrateInhibitor0.5866
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6531
Ames testNon AMES toxic0.8532
CarcinogenicityNon-carcinogens0.8846
BiodegradationNot ready biodegradable0.9685
Rat acute toxicity2.7903 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5
hERG inhibition (predictor II)Inhibitor0.6423
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00592 mg/mLALOGPS
logP4.18ALOGPS
logP3.61ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)9.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.73 m3·mol-1ChemAxon
Polarizability37.55 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. 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
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Enzymes

1. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details
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Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:15