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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H15N.C4H4O4
Molecular Weight 337.3692
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DIZOCILPINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.C[C@]12N[C@H](CC3=CC=CC=C13)C4=CC=CC=C24

InChI

InChIKey=QLTXKCWMEZIHBJ-PJGJYSAQSA-N
InChI=1S/C16H15N.C4H4O4/c1-16-13-8-4-2-6-11(13)10-15(17-16)12-7-3-5-9-14(12)16;5-3(6)1-2-4(7)8/h2-9,15,17H,10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t15-,16+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C16H15N
Molecular Weight 221.297
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

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
Possible mechanism of anticonvulsant effect of ketamine in mice.
2001 Oct
[Ability of novel non-competitive glutamate receptor blocking agents to weaken motor disorders in animals].
2001 Sep
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
Delayed sclerosis, neuroprotection, and limbic epileptogenesis after status epilepticus in the 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
Protection of methylmercury effects on the in vivo dopamine release by NMDA receptor antagonists and nitric oxide synthase inhibitors.
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
Physiological properties of late inspiratory neurons and their possible involvement in inspiratory off-switching in cats.
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
Potentiation of nuclear activator protein-1 DNA binding following brief exposure to N-methyl-D-aspartate in immature cultured rat hippocampal neurons.
2002 Feb 15
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
Changes in dopaminergic and glutamatergic excitatory mechanisms of micturition reflex after middle cerebral artery occlusion in conscious rats.
2002 Jan
Prenatal choline supplementation protects against postnatal neurotoxicity.
2002 Jan 1
Effects of kainic acid on rat body temperature: unmasking by dizocilpine.
2002 Jul
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
Repetitive spreading depression induces nestin protein expression in the cortex of rats and mice. Is this upregulation initiated by N-methyl-D-aspartate receptors?
2002 Mar 8
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
Blockade by N-methyl-D-aspartate of elevation of activator protein-1 binding after stress in rat adrenal gland.
2002 Oct 15
Metabotropic glutamate receptor involvement in phosphoinositide hydrolysis stimulation by an endogenous Na(+), K(+)-ATPase inhibitor and ouabain in neonatal rat brain.
2002 Oct 20
Effects of long-term acetyl-L-carnitine administration in rats: I. increased dopamine output in mesocorticolimbic areas and protection toward acute stress exposure.
2002 Sep
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 Tue Oct 22 13:30:00 UTC 2019
Edited
by admin
on Tue Oct 22 13:30:00 UTC 2019
Record UNII
6LR8C1B66Q
Record Status Validated (UNII)
Record Version
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Name Type Language
DIZOCILPINE MALEATE
MART.   MI   USAN  
USAN  
Official Name English
DIZOCILPINE MALEATE [MART.]
Common Name English
5H-DIBENZO(A,D)CYCLOHEPTEN-5,10-IMINE, 10,11-DIHYDRO-5-METHYL-, (+)-, (Z)-2-BUTENEDIOATE (1:1)
Common Name English
DIZOCILPINE MALEATE [MI]
Common Name English
(+)-10,11-DIHYDRO-5-METHYL-5H-DIBENZO(A,D)CYCLOHEPTEN-5,10-IMINE MALEATE (1:1)
Common Name English
DIZOCILPINE MALEATE [USAN]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
278-614-5
Created by admin on Tue Oct 22 13:30:00 UTC 2019 , Edited by admin on Tue Oct 22 13:30:00 UTC 2019
PRIMARY
EPA CompTox
77086-22-7
Created by admin on Tue Oct 22 13:30:00 UTC 2019 , Edited by admin on Tue Oct 22 13:30:00 UTC 2019
PRIMARY
PUBCHEM
6420042
Created by admin on Tue Oct 22 13:30:00 UTC 2019 , Edited by admin on Tue Oct 22 13:30:00 UTC 2019
PRIMARY
ChEMBL
CHEMBL284237
Created by admin on Tue Oct 22 13:30:00 UTC 2019 , Edited by admin on Tue Oct 22 13:30:00 UTC 2019
PRIMARY
MESH
D016291
Created by admin on Tue Oct 22 13:30:00 UTC 2019 , Edited by admin on Tue Oct 22 13:30:00 UTC 2019
PRIMARY
MERCK INDEX
M4700
Created by admin on Tue Oct 22 13:30:00 UTC 2019 , Edited by admin on Tue Oct 22 13:30:00 UTC 2019
PRIMARY Merck Index
CAS
77086-22-7
Created by admin on Tue Oct 22 13:30:00 UTC 2019 , Edited by admin on Tue Oct 22 13:30:00 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY