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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
SaltsNot Available
Brand namesNot Available
Brand mixturesNot 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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPiperidines
SubclassPhenylpiperidines
Direct parentPhenylpiperidines
Alternative parentsBenzyloxycarbonyls; Benzylethers; Phenethylamines; Tertiary Amines; Carboxylic Acid Esters; Dialkyl Ethers; Polyamines; Enolates
Substituentsbenzyloxycarbonyl; benzylether; phenethylamine; benzene; carboxylic acid ester; tertiary amine; enolate; polyamine; ether; carboxylic acid derivative; dialkyl ether; amine; organonitrogen compound
Classification descriptionThis compound belongs to the phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.988
Blood Brain Barrier + 0.9787
Caco-2 permeable + 0.6548
P-glycoprotein substrate Substrate 0.6775
P-glycoprotein inhibitor I Inhibitor 0.8302
P-glycoprotein inhibitor II Inhibitor 0.5604
Renal organic cation transporter Inhibitor 0.7384
CYP450 2C9 substrate Non-substrate 0.8006
CYP450 2D6 substrate Non-substrate 0.7419
CYP450 3A4 substrate Substrate 0.6116
CYP450 1A2 substrate Non-inhibitor 0.8011
CYP450 2C9 substrate Non-inhibitor 0.803
CYP450 2D6 substrate Inhibitor 0.7905
CYP450 2C19 substrate Non-inhibitor 0.8544
CYP450 3A4 substrate Inhibitor 0.5866
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6531
Ames test Non AMES toxic 0.8532
Carcinogenicity Non-carcinogens 0.8846
Biodegradation Not ready biodegradable 0.9685
Rat acute toxicity 2.7903 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.5
hERG inhibition (predictor II) Inhibitor 0.6423
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility5.92e-03 g/lALOGPS
logP4.18ALOGPS
logP3.61ChemAxon
logS-4.7ALOGPS
pKa (strongest basic)9.24ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count0ChemAxon
polar surface area29.54ChemAxon
rotatable bond count6ChemAxon
refractivity96.73ChemAxon
polarizability37.55ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleYesChemAxon
Spectra
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
ResourceLink
PubChem Compound60977
PubChem Substance46505389
ChemSpider54939
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