Identification
- Generic Name
- Phencyclidine
- DrugBank Accession Number
- DB03575
- Background
A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to ketamine in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (receptors, N-methyl-D-aspartate). As a drug of abuse, it is known as PCP and Angel Dust.
- Type
- Small Molecule
- Groups
- Illicit
- Structure
Structure for Phencyclidine (DB03575)
- Weight
- Average: 243.3871
Monoisotopic: 243.198699805 - Chemical Formula
- C17H25N
- Synonyms
- 1-(1-Phenylcyclohexyl)piperidine
- Fenciclidina
- PCP
- Phencyclidine
- Phencyclidinum
- External IDs
- J4.441E
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
Phencyclidine works primarily as an NMDA receptor antagonist, which blocks the activity of the NMDA Receptor.
- Mechanism of action
The N-methyl-D-Aspartate (NMDA) receptor, a type of ionotropic receptor, is found on the dendrites of neurons and receives signals in the form of neurotransmitters. It is a major excitatory receptor in the brain. Normal physiological function requires that the activated receptor fluxes positive ions through the channel part of the receptor. PCP enters the ion channel from the outside of the neuron and binds, reversibly, to a site in the channel pore, blocking the flux of positive ions into the cell. PCP therefore inhibits depolarization of neurons and interferes with cognitive and other functions of the nervous system.
Target Actions Organism AGlutamate receptor ionotropic, NMDA 3A antagonistHumans USigma non-opioid intracellular receptor 1 Not Available Humans - 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 software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Phencyclidine is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Phencyclidine. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Phencyclidine. Agomelatine The risk or severity of CNS depression can be increased when Phencyclidine is combined with Agomelatine. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Phencyclidine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Phencyclidine hydrochloride V1JZQ7GDTX 956-90-1 BUAJNGPDPGKBGV-UHFFFAOYSA-N - International/Other Brands
- Sernyl (Parke-Davis (discontinued))
Categories
- Drug Categories
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Enzyme Inhibitors
- Excitatory Amino Acid Agents
- Excitatory Amino Acid Antagonists
- Hallucinogens
- Neurotransmitter Agents
- NMDA Receptor Antagonists
- Phencyclidine, antagonists & inhibitors
- Piperidines
- Psychotropic Drugs
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- Aralkylamines
- Alternative Parents
- Cyclohexylamines / Piperidines / Benzene and substituted derivatives / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Cyclohexylamine / Hydrocarbon derivative / Monocyclic benzene moiety / Organoheterocyclic compound / Organopnictogen compound / Piperidine
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- piperidines, benzenes (CHEBI:8058)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- J1DOI7UV76
- CAS number
- 77-10-1
- InChI Key
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N
- InChI
- InChI=1S/C17H25N/c1-4-10-16(11-5-1)17(12-6-2-7-13-17)18-14-8-3-9-15-18/h1,4-5,10-11H,2-3,6-9,12-15H2
- IUPAC Name
- 1-(1-phenylcyclohexyl)piperidine
- SMILES
- C1CCN(CC1)C1(CCCCC1)C1=CC=CC=C1
References
- Synthesis Reference
- US3097136
- General References
- Not Available
- External Links
- KEGG Compound
- C07575
- PubChem Compound
- 6468
- PubChem Substance
- 46508889
- ChemSpider
- 6224
- BindingDB
- 83449
- ChEBI
- 8058
- ChEMBL
- CHEMBL275528
- ZINC
- ZINC000000968311
- PharmGKB
- PA128406980
- PDBe Ligand
- 1PC
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Phencyclidine
- PDB Entries
- 2pcp / 7sab
- MSDS
- Download (70.9 KB)
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
Property Value Source melting point (°C) 46.5 °C PhysProp boiling point (°C) 136 °C at 1.00E+00 mm Hg PhysProp logP 4.69 SANGSTER (1994); ion-corrected avg Caco2 permeability -4.61 ADME Research, USCD pKa 8.29 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.00325 mg/mL ALOGPS logP 5.31 ALOGPS logP 4.49 Chemaxon logS -4.9 ALOGPS pKa (Strongest Basic) 10.56 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 3.24 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 77.65 m3·mol-1 Chemaxon Polarizability 29.66 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 No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9861 Blood Brain Barrier + 0.9904 Caco-2 permeable + 0.8867 P-glycoprotein substrate Substrate 0.5631 P-glycoprotein inhibitor I Non-inhibitor 0.7823 P-glycoprotein inhibitor II Non-inhibitor 0.7682 Renal organic cation transporter Inhibitor 0.7233 CYP450 2C9 substrate Non-substrate 0.8234 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.572 CYP450 1A2 substrate Inhibitor 0.5408 CYP450 2C9 inhibitor Non-inhibitor 0.8982 CYP450 2D6 inhibitor Inhibitor 0.9296 CYP450 2C19 inhibitor Inhibitor 0.5804 CYP450 3A4 inhibitor Non-inhibitor 0.6982 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7711 Ames test Non AMES toxic 0.8601 Carcinogenicity Non-carcinogens 0.9126 Biodegradation Not ready biodegradable 0.9671 Rat acute toxicity 3.6064 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7922 hERG inhibition (predictor II) Inhibitor 0.6568
Spectra
- Mass Spec (NIST)
- Download (9.68 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 164.2063619 predictedDarkChem Lite v0.1.0 [M-H]- 160.01205 predictedDeepCCS 1.0 (2019) [M+H]+ 164.7999619 predictedDarkChem Lite v0.1.0 [M+H]+ 162.37006 predictedDeepCCS 1.0 (2019) [M+Na]+ 164.9462619 predictedDarkChem Lite v0.1.0 [M+Na]+ 168.46321 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Protein phosphatase 2a binding
- Specific Function
- NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May ...
- Gene Name
- GRIN3A
- Uniprot ID
- Q8TCU5
- Uniprot Name
- Glutamate receptor ionotropic, NMDA 3A
- Molecular Weight
- 125464.07 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Opioid receptor activity
- Specific Function
- Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma m...
- Gene Name
- SIGMAR1
- Uniprot ID
- Q99720
- Uniprot Name
- Sigma non-opioid intracellular receptor 1
- Molecular Weight
- 25127.52 Da
References
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Shebley M, Kent UM, Ballou DP, Hollenberg PF: Mechanistic analysis of the inactivation of cytochrome P450 2B6 by phencyclidine: effects on substrate binding, electron transfer, and uncoupling. Drug Metab Dispos. 2009 Apr;37(4):745-52. doi: 10.1124/dmd.108.024661. Epub 2009 Jan 14. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
Drug created at June 13, 2005 13:24 / Updated at November 03, 2023 23:50