DIZOCILPINE MALEATE

Details

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

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.C[C@]12N[C@H](CC3=C1C=CC=C3)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	C16H15N
Molecular Weight	221.297
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20716924 | DOI: 10.1016/S0165-6147(97)01164-4 | https://www.ncbi.nlm.nih.gov/pubmed/15916843 | Bihari, D., Holaday, J.W. (2012) Brain Failure, retrieved from: https://books.google.ru/books?id=bTKSBgAAQBAJ

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

Title	Date	PubMed
Excitotoxicity-induced expression of amyloid precursor protein (beta-APP) in the hippocampus and cortex of rat brain. an electron-microscopy and biochemical study.	2001	11770127
Possible mechanism of anticonvulsant effect of ketamine in mice.	2001 Oct	11883507
[Ability of novel non-competitive glutamate receptor blocking agents to weaken motor disorders in animals].	2001 Sep	11763540
Glutamate-induced delta-catenin redistribution and dissociation from postsynaptic receptor complexes.	2002	12453475
Involvement of N-methyl-D-aspartate receptors in nociception in the cyclophosphamide-induced vesical pain model in the conscious rat.	2002	12161096
Delayed sclerosis, neuroprotection, and limbic epileptogenesis after status epilepticus in the rat.	2002	12121301
Interactions between cutaneous afferent inputs to a withdrawal reflex in the decerebrated rabbit and their control by descending and segmental systems.	2002	12074898
Dizocilpine infusion has a different effect in the development of morphine and cocaine sensitization: behavioral and neurochemical aspects.	2002	11801363
Endogenous excitatory amino acid neurotransmission regulates thyroid-stimulating hormone and thyroid hormone secretion in conscious freely moving male rats.	2002 Apr	12108519
Behavioral effects of MK-801 on reserpine-treated mice.	2002 Apr	11999899
Protection of methylmercury effects on the in vivo dopamine release by NMDA receptor antagonists and nitric oxide synthase inhibitors.	2002 Apr	11985818
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	11907185
NMDA receptor antagonists impair motor performance in immature rats.	2002 Aug	12172689
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	12151550
Ammonia-induced extracellular accumulation of taurine in the rat striatum in vivo: role of ionotropic glutamate receptors.	2002 Feb	11926274
Physiological properties of late inspiratory neurons and their possible involvement in inspiratory off-switching in cats.	2002 Feb	11826069
Sexually dimorphic effects of morphine and MK-801: sex steroid-dependent and -independent mechanisms.	2002 Feb	11796656
MK801 suppresses the L-DOPA-induced increase of glutamate in striatum of hemi-Parkinson rats.	2002 Feb 1	11814417
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	11835319
Extradural compression of sensorimotor cortex: a useful model for studies on ischemic brain damage and neuroprotection.	2002 Jan	11852980
Melanin concentrating hormone increase hippocampal synaptic transmission in the rat.	2002 Jan	11814630
Changes in dopaminergic and glutamatergic excitatory mechanisms of micturition reflex after middle cerebral artery occlusion in conscious rats.	2002 Jan	11771945
Prenatal choline supplementation protects against postnatal neurotoxicity.	2002 Jan 1	11756524
Effects of kainic acid on rat body temperature: unmasking by dizocilpine.	2002 Jul	12213256
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	12122485
N-Methyl-D-aspartate receptor blockade by dizocilpine prevents stress-induced sudden death in cardiomyopathic hamsters.	2002 Jul 19	12106681
Low doses of dizocilpine block the development and subsequent expression of locomotor sensitization to nicotine in rats.	2002 Jun	12073164
Discriminative stimulus effects of ethanol in C57BL/6J and DBA/2J inbred mice.	2002 Jun	12068241
Dizocilpine inhibits amphetamine-induced formation of nitric oxide and amphetamine-induced release of amino acids and acetylcholine in the rat brain.	2002 Mar	11958521
Cerebral glucose utilization in transgenic mice overexpressing heat shock protein 70 is altered by dizocilpine.	2002 Mar	11918653
Enhancement of the discriminative stimulus effects of phencyclidine by the tetracycline antibiotics doxycycline and minocycline in rats.	2002 Mar	11889503
Nitric-oxide-synthase-mediated cyclic guanosine monophosphate production in neonatal rat cerebellar prisms is resistant to calcineurin inhibition.	2002 Mar 29	11958839
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	11852186
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	12045473
Involvement of dopaminergic system in the nucleus accumbens in the discriminative stimulus effects of phencyclidine.	2002 May	12015202
Relative reinforcing strength of three N-methyl-D-aspartate antagonists with different onsets of action.	2002 May	11961074
NMDA receptor involvement in imipramine withdrawal-associated effects on swim stress, GABA levels and NMDA receptor binding in rat hippocampus.	2002 May 24	12020747
SR146131, a cholecystokinin-A receptor agonist, antagonizes prepulse inhibition deficits produced by dizocilpine and DOI.	2002 Nov	12424552
Blockade of ionotropic glutamatergic transmission in the ventral tegmental area reduces heroin reinforcement in rat.	2002 Nov	12404076
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	12390525
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	12372903
Differential effects of direct and indirect dopamine agonists on prepulse inhibition: a study in D1 and D2 receptor knock-out mice.	2002 Nov 1	12417685
Valproate prevents the induction and the expression of MK-801 sensitization.	2002 Nov 8	12414098
Altered responses to dizocilpine maleate administration in ethanol-withdrawn male and female rats.	2002 Oct	12457939
Effects of puerarin on scopolamine-, mecamylamine-, p-chloroamphetamine- and dizocilpine-induced inhibitory avoidance performance impairment in rats.	2002 Oct	12391553
Blockade by N-methyl-D-aspartate of elevation of activator protein-1 binding after stress in rat adrenal gland.	2002 Oct 15	12271465
Metabotropic glutamate receptor involvement in phosphoinositide hydrolysis stimulation by an endogenous Na(+), K(+)-ATPase inhibitor and ouabain in neonatal rat brain.	2002 Oct 20	12354644
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	12225698
Synaptic mechanisms of inspiratory off-switching evoked by pontine pneumotaxic stimulation in cats.	2002 Sep	12204298
Affinity and specificity of N-methyl- D-aspartate channel blockers affect their ability to disrupt prepulse inhibition of acoustic startle in rats.	2003 Feb	12459931

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:12:19 GMT 2023` Edited by `admin` on `Fri Dec 15 17:12:19 GMT 2023`
Record UNII	6LR8C1B66Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIZOCILPINE MALEATE

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