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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H15N
Molecular Weight 221.2976
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIZOCILPINE

SMILES

C[C@]12c3ccccc3C[C@]([H])(c4ccccc41)N2

InChI

InChIKey=LBOJYSIDWZQNJS-CVEARBPZSA-N
InChI=1S/C16H15N/c1-16-13-8-4-2-6-11(13)10-15(17-16)12-7-3-5-9-14(12)16/h2-9,15,17H,10H2,1H3/t15-,16+/m1/s1

HIDE SMILES / InChI

Molecular Formula C16H15N
Molecular Weight 221.2976
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Dizocilpine (MK-801) is an antagonist of the N-methyl-D-aspartate (NMDA) receptor in the glutamate category involved with the central nervous system (CNS). The drug displays a variety of physiological actions, many of which involve the CNS, such as anesthetic and anticonvulsant properties. It penetrates readily into CNS and was described as the agent with central sympathomimetic properties. Co-administration of dizocilpine with psychostimulants, such as cocaine, amphetamine and nicotine, has been reported to prevent the development of behavioural sensitization to these drugs as well as associated neuroadaptations in rodents. However, studies with bromocriptine have suggested that co-administration of dizocilpine might merely cause sensitization to become state-dependent. A single injection of MK-801 to rats models both positive and negative symptoms of schizophrenia. Treatment of mice with dizocilpine induced learning impairment.

Approval Year

PubMed

PubMed

TitleDatePubMed
Excitotoxicity-induced expression of amyloid precursor protein (beta-APP) in the hippocampus and cortex of rat brain. an electron-microscopy and biochemical study.
2001
[3H]acetycholine release in rat striatal slices is not subject to dopamine heteroreceptor supersensitivity 30 months after 6-hydroxydopamine lesion of the substantia nigra.
2001 Apr
NMDA antagonists produce site-selective impairment of accuracy in a delayed nonmatch-to-sample task in rats.
2001 Dec
N-methyl-D-aspartate receptor antagonists potentiate the antinociceptive effects of morphine in squirrel monkeys.
2001 Jul
Blockade of the central generator of locomotor rhythm by noncompetitive NMDA receptor antagonists in Drosophila larvae.
2001 Jul
Two distinct oscillatory states determined by the NMDA receptor in rat inferior olive.
2001 Jul 1
Comparison of apomorphine, amphetamine and dizocilpine disruptions of prepulse inhibition in inbred and outbred mice strains.
2001 Jul 13
Excitatory mechanisms in neuroleptic-induced vacuous chewing movements (VCMs): possible involvement of calcium and nitric oxide.
2001 Jun
Microdialysates of amines and metabolites from core nucleus accumbens of freely moving rats are altered by dizocilpine.
2001 May 25
Possible mechanism of anticonvulsant effect of ketamine in mice.
2001 Oct
Effects of N-methyl-D-aspartate agonists and antagonists in rats discriminating amphetamine.
2001 Sep
Mapping of brain activation in response to pharmacological agents using fMRI in the rat.
2001 Sep
The NMDA receptor complex: a promising target for novel antiepileptic strategies.
2001 Sep
Absence of MK801-induced inspiratory prolongation in chronically hypoxic rats.
2001 Sep 28
Glutamate-induced delta-catenin redistribution and dissociation from postsynaptic receptor complexes.
2002
Involvement of N-methyl-D-aspartate receptors in nociception in the cyclophosphamide-induced vesical pain model in the conscious rat.
2002
Interactions between cutaneous afferent inputs to a withdrawal reflex in the decerebrated rabbit and their control by descending and segmental systems.
2002
Dizocilpine infusion has a different effect in the development of morphine and cocaine sensitization: behavioral and neurochemical aspects.
2002
Endogenous excitatory amino acid neurotransmission regulates thyroid-stimulating hormone and thyroid hormone secretion in conscious freely moving male rats.
2002 Apr
Behavioral effects of MK-801 on reserpine-treated mice.
2002 Apr
Effects of (+/-)-4-[[2-(1-methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride (SIB-1553A), a selective ligand for nicotinic acetylcholine receptors, in tests of visual attention and distractibility in rats and monkeys.
2002 Apr
NMDA receptor antagonists impair motor performance in immature rats.
2002 Aug
Severe impairment of NMDA receptor function in mice carrying targeted point mutations in the glycine binding site results in drug-resistant nonhabituating hyperactivity.
2002 Aug 1
Ammonia-induced extracellular accumulation of taurine in the rat striatum in vivo: role of ionotropic glutamate receptors.
2002 Feb
Sexually dimorphic effects of morphine and MK-801: sex steroid-dependent and -independent mechanisms.
2002 Feb
MK801 suppresses the L-DOPA-induced increase of glutamate in striatum of hemi-Parkinson rats.
2002 Feb 1
Extradural compression of sensorimotor cortex: a useful model for studies on ischemic brain damage and neuroprotection.
2002 Jan
Melanin concentrating hormone increase hippocampal synaptic transmission in the rat.
2002 Jan
Characterization of the discriminative stimulus effects of N-methyl- D-aspartate ligands under different ethanol training conditions in the cynomolgus monkey ( Macaca fascicularis).
2002 Jul
N-Methyl-D-aspartate receptor blockade by dizocilpine prevents stress-induced sudden death in cardiomyopathic hamsters.
2002 Jul 19
Low doses of dizocilpine block the development and subsequent expression of locomotor sensitization to nicotine in rats.
2002 Jun
Discriminative stimulus effects of ethanol in C57BL/6J and DBA/2J inbred mice.
2002 Jun
Dizocilpine inhibits amphetamine-induced formation of nitric oxide and amphetamine-induced release of amino acids and acetylcholine in the rat brain.
2002 Mar
Cerebral glucose utilization in transgenic mice overexpressing heat shock protein 70 is altered by dizocilpine.
2002 Mar
Enhancement of the discriminative stimulus effects of phencyclidine by the tetracycline antibiotics doxycycline and minocycline in rats.
2002 Mar
Nitric-oxide-synthase-mediated cyclic guanosine monophosphate production in neonatal rat cerebellar prisms is resistant to calcineurin inhibition.
2002 Mar 29
Acamprosate has no effect on NMDA-induced toxicity but reduces toxicity induced by spermidine or by changing the medium in organotypic hippocampal slice cultures from rat.
2002 May
Involvement of dopaminergic system in the nucleus accumbens in the discriminative stimulus effects of phencyclidine.
2002 May
Relative reinforcing strength of three N-methyl-D-aspartate antagonists with different onsets of action.
2002 May
NMDA receptor involvement in imipramine withdrawal-associated effects on swim stress, GABA levels and NMDA receptor binding in rat hippocampus.
2002 May 24
SR146131, a cholecystokinin-A receptor agonist, antagonizes prepulse inhibition deficits produced by dizocilpine and DOI.
2002 Nov
Blockade of ionotropic glutamatergic transmission in the ventral tegmental area reduces heroin reinforcement in rat.
2002 Nov
Striatal dopamine-NMDA receptor interactions in the modulation of glutamate release in the substantia nigra pars reticulata in vivo: opposite role for D1 and D2 receptors.
2002 Nov
Excitatory amino acid-elicited tonic convulsions in mice and N-methyl-D-aspartate receptor activation: role of Ca(2+) influx and involvement of intracellular Ca(2+)-dependent biochemical processes.
2002 Nov
Differential effects of direct and indirect dopamine agonists on prepulse inhibition: a study in D1 and D2 receptor knock-out mice.
2002 Nov 1
Valproate prevents the induction and the expression of MK-801 sensitization.
2002 Nov 8
Altered responses to dizocilpine maleate administration in ethanol-withdrawn male and female rats.
2002 Oct
Effects of puerarin on scopolamine-, mecamylamine-, p-chloroamphetamine- and dizocilpine-induced inhibitory avoidance performance impairment in rats.
2002 Oct
Synaptic mechanisms of inspiratory off-switching evoked by pontine pneumotaxic stimulation in cats.
2002 Sep
Affinity and specificity of N-methyl- D-aspartate channel blockers affect their ability to disrupt prepulse inhibition of acoustic startle in rats.
2003 Feb
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:09:00 UTC 2021
Edited
by admin
on Sat Jun 26 09:09:00 UTC 2021
Record UNII
7PY8KH681I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIZOCILPINE
HSDB   INN   MI   WHO-DD  
INN  
Official Name English
DIZOCILPINE [MI]
Common Name English
MK-801
Code English
5H-DIBENZO(A,D)CYCLOHEPTEN-5,10-IMINE, 10,11-DIHYDRO-5-METHYL-, (+)-
Common Name English
(+)-10,11-DIHYDRO-5-METHYL-5H-DIBENZO(A,D)CYCLOHEPTEN-5,10-IMINE
Common Name English
DIZOCILPINE [HSDB]
Common Name English
DIZOCILPINE [INN]
Common Name English
DIZOCILPINE [WHO-DD]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 605204
Created by admin on Sat Jun 26 09:09:00 UTC 2021 , Edited by admin on Sat Jun 26 09:09:00 UTC 2021
NCI_THESAURUS C264
Created by admin on Sat Jun 26 09:09:00 UTC 2021 , Edited by admin on Sat Jun 26 09:09:00 UTC 2021
Code System Code Type Description
EPA CompTox
77086-21-6
Created by admin on Sat Jun 26 09:09:00 UTC 2021 , Edited by admin on Sat Jun 26 09:09:00 UTC 2021
PRIMARY
EVMPD
SUB06341MIG
Created by admin on Sat Jun 26 09:09:00 UTC 2021 , Edited by admin on Sat Jun 26 09:09:00 UTC 2021
PRIMARY
PUBCHEM
180081
Created by admin on Sat Jun 26 09:09:00 UTC 2021 , Edited by admin on Sat Jun 26 09:09:00 UTC 2021
PRIMARY
HSDB
7641
Created by admin on Sat Jun 26 09:09:00 UTC 2021 , Edited by admin on Sat Jun 26 09:09:00 UTC 2021
PRIMARY
FDA UNII
7PY8KH681I
Created by admin on Sat Jun 26 09:09:00 UTC 2021 , Edited by admin on Sat Jun 26 09:09:00 UTC 2021
PRIMARY
NCI_THESAURUS
C65450
Created by admin on Sat Jun 26 09:09:00 UTC 2021 , Edited by admin on Sat Jun 26 09:09:00 UTC 2021
PRIMARY
MERCK INDEX
M4700
Created by admin on Sat Jun 26 09:09:00 UTC 2021 , Edited by admin on Sat Jun 26 09:09:00 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL284237
Created by admin on Sat Jun 26 09:09:00 UTC 2021 , Edited by admin on Sat Jun 26 09:09:00 UTC 2021
PRIMARY
CAS
77086-21-6
Created by admin on Sat Jun 26 09:09:00 UTC 2021 , Edited by admin on Sat Jun 26 09:09:00 UTC 2021
PRIMARY
INN
6320
Created by admin on Sat Jun 26 09:09:00 UTC 2021 , Edited by admin on Sat Jun 26 09:09:00 UTC 2021
PRIMARY
WIKIPEDIA
DIZOCILPINE
Created by admin on Sat Jun 26 09:09:00 UTC 2021 , Edited by admin on Sat Jun 26 09:09:00 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY