1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine

Identification

Name
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine
Accession Number
DB01562
Type
Small Molecule
Groups
Experimental, 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
  • 1-(2-Phenethyl)-4-phenyl-4-acetoxypiperidine
  • 1-phenethyl-4-phenyl-4-piperidinol acetate
  • PEPAP
External IDs
DEA No. 9663 / IDS-NP-026 / IDS-NP-026(SECT.3) / MCV 4527 / NIH 10460
Product Ingredients
Not Available
Approved Prescription Products
Not Available
Approved Generic Prescription Products
Not Available
Approved Over the Counter Products
Not Available
Unapproved/Other Products
Not Available
International/Other Brands
Not Available
Brand mixtures
Not Available
Categories
Not Available
UNII
T6LN72I828
CAS number
64-52-8
Weight
Average: 323.4287
Monoisotopic: 323.188529049
Chemical Formula
C21H25NO2
InChI Key
BVURVTVDNWSNFN-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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
  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:12006905 ]
External Links
PubChem Compound
60977
PubChem Substance
46505389
ChemSpider
54939
ChEMBL
CHEMBL2361014
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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
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 inhibitorNon-inhibitor0.803
CYP450 2D6 inhibitorInhibitor0.7905
CYP450 2C19 inhibitorNon-inhibitor0.8544
CYP450 3A4 inhibitorInhibitor0.5866
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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted LC-MS/MS Spectrum - 10V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 10V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, NegativePredicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Phenylpiperidines
Direct Parent
Phenylpiperidines
Alternative Parents
Benzyloxycarbonyls / Phenethylamines / Aralkylamines / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic oxides
show 2 more
Substituents
Phenylpiperidine / Benzyloxycarbonyl / Phenethylamine / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Amino acid or derivatives / Tertiary aliphatic amine / Tertiary amine / Carboxylic acid ester
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
Drug created on July 31, 2007 07:10 / Updated on September 01, 2017 10:41