Phencyclidine

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
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

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Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AGlutamate receptor ionotropic, NMDA 3A
antagonist
Humans
USigma non-opioid intracellular receptor 1Not AvailableHumans
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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Phencyclidine is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Phencyclidine.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Phencyclidine.
AgomelatineThe risk or severity of CNS depression can be increased when Phencyclidine is combined with Agomelatine.
AlfentanilThe risk or severity of CNS depression can be increased when Alfentanil is combined with Phencyclidine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Phencyclidine hydrochlorideV1JZQ7GDTX956-90-1BUAJNGPDPGKBGV-UHFFFAOYSA-N
International/Other Brands
Sernyl (Parke-Davis (discontinued))

Categories

Drug Categories
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
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
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)46.5 °CPhysProp
boiling point (°C)136 °C at 1.00E+00 mm HgPhysProp
logP4.69SANGSTER (1994); ion-corrected avg
Caco2 permeability-4.61ADME Research, USCD
pKa8.29SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.00325 mg/mLALOGPS
logP5.31ALOGPS
logP4.49Chemaxon
logS-4.9ALOGPS
pKa (Strongest Basic)10.56Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area3.24 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity77.65 m3·mol-1Chemaxon
Polarizability29.66 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9861
Blood Brain Barrier+0.9904
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.5631
P-glycoprotein inhibitor INon-inhibitor0.7823
P-glycoprotein inhibitor IINon-inhibitor0.7682
Renal organic cation transporterInhibitor0.7233
CYP450 2C9 substrateNon-substrate0.8234
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.572
CYP450 1A2 substrateInhibitor0.5408
CYP450 2C9 inhibitorNon-inhibitor0.8982
CYP450 2D6 inhibitorInhibitor0.9296
CYP450 2C19 inhibitorInhibitor0.5804
CYP450 3A4 inhibitorNon-inhibitor0.6982
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7711
Ames testNon AMES toxic0.8601
CarcinogenicityNon-carcinogens0.9126
BiodegradationNot ready biodegradable0.9671
Rat acute toxicity3.6064 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7922
hERG inhibition (predictor II)Inhibitor0.6568
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.68 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-0uyl-9740000000-a1aa5f844f1483af1bc7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0190000000-236fee1bfe6cb40bf396
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-06ec3ac71d792b805e4c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-3940000000-497edfa42b5bac713fa9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-45f4a938ae4c25edeb73
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a7i-9820000000-bcbdf4d8c9e082c5733a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9610000000-241a36202ec3d42fa1c7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-164.2063619
predicted
DarkChem Lite v0.1.0
[M-H]-160.01205
predicted
DeepCCS 1.0 (2019)
[M+H]+164.7999619
predicted
DarkChem Lite v0.1.0
[M+H]+162.37006
predicted
DeepCCS 1.0 (2019)
[M+Na]+164.9462619
predicted
DarkChem Lite v0.1.0
[M+Na]+168.46321
predicted
DeepCCS 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Enzymes

Details
1. Cytochrome P450 2B6
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
  1. 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]
  2. 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 March 03, 2024 02:34