Identification
- Generic Name
- 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine
- DrugBank Accession Number
- DB01562
- Background
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine (PEPAP) is a synthetic analogue of meperidine. It is sold as a "synthetic heroin."
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Structure
Structure for 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine (DB01562)
- Weight
- Average: 323.4287
Monoisotopic: 323.188529049 - Chemical Formula
- C21H25NO2
- Synonyms
- 1-(2-Phenethyl)-4-phenyl-4-acetoxypiperidine
- 1-Phenethyl-4-phenyl-4-piperidinol acetate (ester)
- PEPAP
- External IDs
- DEA No. 9663
- IDS-NP-026
- IDS-NP-026(SECT.3)
- MCV 4527
- NIH 10460
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The metabolism of Acebutolol can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine. Almotriptan The metabolism of Almotriptan can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine. Alogliptin The metabolism of Alogliptin can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine. Aminophenazone The metabolism of Aminophenazone can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzyloxycarbonyl / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester show 13 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- T6LN72I828
- CAS number
- 64-52-8
- 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
References
- General 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. doi: 10.1097/00004714-200206000-00015. [Article]
- External Links
- PubChem Compound
- 60977
- PubChem Substance
- 46505389
- ChemSpider
- 54939
- ChEMBL
- CHEMBL2361014
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
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
Property Value Source Water Solubility 0.00592 mg/mL ALOGPS logP 4.18 ALOGPS logP 3.61 Chemaxon logS -4.7 ALOGPS pKa (Strongest Basic) 9.24 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 29.54 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 96.73 m3·mol-1 Chemaxon Polarizability 37.55 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - 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 inhibitor Non-inhibitor 0.803 CYP450 2D6 inhibitor Inhibitor 0.7905 CYP450 2C19 inhibitor Non-inhibitor 0.8544 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0049000000-1a7ea63a7c45b16fc629 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-9000000000-448ab03443271bae92e8 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a59-7192000000-3e3d75454b0a18265ff5 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0293000000-36b536e24899c7a38e28 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-052f-5950000000-6ee35ab6b2d1e833f1c5 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-08ml-3912000000-938104204193feddcb1d Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 184.8253039 predictedDarkChem Lite v0.1.0 [M-H]- 170.02551 predictedDeepCCS 1.0 (2019) [M+H]+ 185.4262039 predictedDarkChem Lite v0.1.0 [M+H]+ 172.38351 predictedDeepCCS 1.0 (2019) [M+Na]+ 185.4521039 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.7459 predictedDeepCCS 1.0 (2019)
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- This enzyme action is supported by an in vitro study. Clinical correlation is 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
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. doi: 10.1097/00004714-200206000-00015. [Article]
Drug created at July 31, 2007 13:10 / Updated at June 12, 2020 16:51