U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H25N
Molecular Weight 243.3871
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENCYCLIDINE

SMILES

C1CCN(CC1)C2(CCCCC2)C3=CC=CC=C3

InChI

InChIKey=JTJMJGYZQZDUJJ-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C17H25N
Molecular Weight 243.3871
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Phencyclidine is an illegal, hallucinogenic drug that was initially used as an anesthetic agent in the 1950s and early 1960s, but was then withdrawn in 1965 because of dissociative hallucinogenic effects that were often disturbing and sometimes severe and prolonged. Phencyclidine is a noncompetitive NMDA (N-methyl-D-aspartate) receptor antagonist and glutamate receptor antagonist, but also interacts with other receptor sites, and may have effects with dopamine, opioid and nicotinic receptors. Phencyclidine disrupts the functioning of receptors for the neurotransmitter glutamate, which plays a major role in the perception of pain as well as in learning, memory, and emotion. It also influences the actions of the neurotransmitter dopamine, which causes the euphoria associated with drug use. Phencyclidine overdose deaths may occur after taking a large dose, though many phencyclidine related deaths result from delusions and other psychological consequences of the drug’s use. There have been reports of death due to accidental drowning, leaping from high places, and motor vehicle accidents in addition to violent episodes of self-mutilation, suicides, and homicides.

Approval Year

PubMed

PubMed

TitleDatePubMed
Anticonvulsant efficacy of N-methyl-D-aspartate antagonists against convulsions induced by cocaine.
1999 May
Relation between hippocampal gamma waves and behavioral disturbances induced by phencyclidine and methamphetamine.
2000 Jun 15
Differential regulation of chromogranin A, chromogranin B and secretogranin II in rat brain by phencyclidine treatment.
2001
Combinations of clozapine and phencyclidine: effects on drug discrimination and behavioral inhibition in rats.
2001
Subchronic treatment with methamphetamine and phencyclidine differentially alters the adenosine A1 and A2A receptors in the prefrontal cortex, hippocampus, and striatum of the rat.
2001 Apr
Qualitative screening for drugs of abuse in hair using GC-MS.
2001 Apr
Phencyclidine impairs latent learning in mice: interaction between glutamatergic systems and sigma(1) receptors.
2001 Apr
Neonatal phencyclidine treatment selectively attenuates mesolimbic dopamine function in adult rats as revealed by methamphetamine-induced behavior and c-fos mRNA expression in the brain.
2001 Apr
Elucidating the role of muscarinic receptors in psychosis.
2001 Apr 27
SB-243213; a selective 5-HT2C receptor inverse agonist with improved anxiolytic profile: lack of tolerance and withdrawal anxiety.
2001 Aug
Combined alpha 2-adrenergic/D2 dopamine receptor blockade fails to reproduce the ability of clozapine to reverse phencyclidine-induced deficits in prepulse inhibition of startle.
2001 Dec
Effects of thienylphencyclidine (TCP) on seizure activity and brain damage produced by soman in guinea-pigs: ECoG correlates of neurotoxicity.
2001 Feb
Uncompetitive antagonists of the N-methyl-D-aspartate (NMDA) receptors alter the mRNA expression of proteins associated with the NMDA receptor complex.
2001 Feb
The Maternal Lifestyle Study: drug use by meconium toxicology and maternal self-report.
2001 Feb
Phencyclidine-induced discriminative stimulus is mediated via phencyclidine binding sites on the N-methyl-D-aspartate receptor-ion channel complex, not via sigma(1) receptors.
2001 Feb 15
A conformational intermediate between the resting and desensitized states of the nicotinic acetylcholine receptor.
2001 Feb 16
Impaired inhibition of conditioned responses produced by subchronic administration of phencyclidine to rats.
2001 Jan
The effects of phencyclidine pretreatment on amphetamine-induced behavior and c-Fos expression in the rat.
2001 Jan 12
Clozapine, but not haloperidol, reverses social behavior deficit in mice during withdrawal from chronic phencyclidine treatment.
2001 Jan 22
Effects of a novel, selective, sigma1-ligand, MS-377, on phencyclidine-induced behaviour.
2001 Jul
Blockade of the central generator of locomotor rhythm by noncompetitive NMDA receptor antagonists in Drosophila larvae.
2001 Jul
[Acting out and psychoactive substances: alcohol, drugs, illicit substances].
2001 Jul-Aug
Discrimination of pentobarbital doses and drug mixtures under fixed-ratio and fixed-interval reinforcement schedules.
2001 Jun
Advances in schizophrenia.
2001 Jun
Detection of analytes by immunoassay using up-converting phosphor technology.
2001 Jun 1
Role of the NMDA receptor subunit in the expression of the discriminative stimulus effect induced by ketamine.
2001 Jun 29
Site-specific charge interactions of alpha-conotoxin MI with the nicotinic acetylcholine receptor.
2001 Jun 29
Structure and polymorphisms of the human metabotropic glutamate receptor type 2 gene (GRM2): analysis of association with schizophrenia.
2001 Mar
Effects of competitive and non-competitive NMDA receptor antagonists on dopamine output in the shell and core subdivisions of the nucleus accumbens.
2001 Mar
Increased expression of neuronal Src and tyrosine phosphorylation of NMDA receptors in rat brain after systemic treatment with MK-801.
2001 Mar
Pharmacological characterization of locomotor sensitization induced by chronic phencyclidine administration.
2001 Mar
Differential and region-specific activation of mitogen-activated protein kinases following chronic administration of phencyclidine in rat brain.
2001 Mar
Increase in number and size of kidney concretions as a result of PCP exposure in the freshwater snail Planorbarius corneus (Gastropoda, Pulmonata).
2001 Mar 9
The effects of phencyclidine pretreatment on cocaine-mediated hepatotoxicity in mice.
2001 May 1
Ketamine as a street drug.
2001 Nov
Gamma vinyl-GABA differentially modulates NMDA antagonist-induced increases in mesocortical versus mesolimbic DA transmission.
2001 Nov
Effects of amphetamine, dexfenfluramine, diazepam, and other pharmacological and dietary manipulations on food "seeking" and "taking" behavior in non-human primates.
2001 Oct
NMDA receptors as targets for drug action in neuropathic pain.
2001 Oct 19
Neuroprotective and behavioral effects of the selective metabotropic glutamate mGlu(1) receptor antagonist BAY 36-7620.
2001 Oct 5
Phencyclidine-induced dysregulation of dopamine response to amphetamine in prefrontal cortex and striatum.
2001 Sep
Differential effects of delta 9-THC on spatial reference and working memory in mice.
2001 Sep
Expression of excitatory amino acid transporter transcripts in the thalamus of subjects with schizophrenia.
2001 Sep
Biphasic modulation of NMDA-induced responses in pyramidal cells of the medial prefrontal cortex by Y-931, a potential atypical antipsychotic drug.
2001 Sep 15
Cembranoid and long-chain alkanol sites on the nicotinic acetylcholine receptor and their allosteric interaction.
2001 Sep 18
Enhancement of immobility induced by repeated phencyclidine injection: association with c-Fos protein in the mouse brain.
2001 Sep 28
Gacyclidine: a new neuroprotective agent acting at the N-methyl-D-aspartate receptor.
2001 Summer
Cocaine-induced conditioned place preference in mice: induction, extinction and reinstatement by related psychostimulants.
2002 Jan
Amphetamine inhibits the N-methyl-D-aspartate receptor-mediated responses by directly interacting with the receptor/channel complex.
2002 Mar
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 16:34:02 GMT 2023
Edited
by admin
on Fri Dec 15 16:34:02 GMT 2023
Record UNII
J1DOI7UV76
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENCYCLIDINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
phencyclidine [INN]
Common Name English
ANGEL DUST
Common Name English
PHENYLCYCLIDINE
Common Name English
PHENCYCLIDINE [MI]
Common Name English
J4.441E
Code English
PCP
Common Name English
Tic Tac
Common Name English
HOG
Common Name English
PHENCYCLIDINE [VANDF]
Common Name English
Phencyclidine [WHO-DD]
Common Name English
PHENCYCLINE
Common Name English
1-(1-PHENYLCYCLOHEXYL)PIPERIDINE
Systematic Name English
Angel Dust
Common Name English
PHENCYCLIDINE [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
DEA NO. 7471
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C738
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
WIKIPEDIA
PHENCYCLIDINE
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
MESH
D010622
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
CHEBI
8058
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
PUBCHEM
6468
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
HSDB
6472
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
MERCK INDEX
m8603
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID6023446
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
LACTMED
Phencyclidine
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
INN
1058
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
DRUG BANK
DB03575
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
EVMPD
SUB09755MIG
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
SMS_ID
100000085809
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
CAS
77-10-1
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
ChEMBL
CHEMBL275528
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
FDA UNII
J1DOI7UV76
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
DRUG CENTRAL
2121
Created by admin on Fri Dec 15 16:34:02 GMT 2023 , Edited by admin on Fri Dec 15 16:34:02 GMT 2023
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
MAJOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
PRECURSOR->PARENT
TRANSPORTER -> INHIBITOR
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