DIZOCILPINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H15N
Molecular Weight	221.297
Optical Activity	( + )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12N[C@H](CC3=CC=CC=C13)C4=CC=CC=C24

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	221.297
Charge	0
Count

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

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
Affinity and specificity of N-methyl- D-aspartate channel blockers affect their ability to disrupt prepulse inhibition of acoustic startle in rats.	2003-02	12459931
Valproate prevents the induction and the expression of MK-801 sensitization.	2002-11-08	12414098
Differential effects of direct and indirect dopamine agonists on prepulse inhibition: a study in D1 and D2 receptor knock-out mice.	2002-11-01	12417685
SR146131, a cholecystokinin-A receptor agonist, antagonizes prepulse inhibition deficits produced by dizocilpine and DOI.	2002-11	12424552
Blockade of ionotropic glutamatergic transmission in the ventral tegmental area reduces heroin reinforcement in rat.	2002-11	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.	2002-11	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.	2002-11	12372903
Metabotropic glutamate receptor involvement in phosphoinositide hydrolysis stimulation by an endogenous Na(+), K(+)-ATPase inhibitor and ouabain in neonatal rat brain.	2002-10-20	12354644
Blockade by N-methyl-D-aspartate of elevation of activator protein-1 binding after stress in rat adrenal gland.	2002-10-15	12271465
Altered responses to dizocilpine maleate administration in ethanol-withdrawn male and female rats.	2002-10	12457939
Effects of puerarin on scopolamine-, mecamylamine-, p-chloroamphetamine- and dizocilpine-induced inhibitory avoidance performance impairment in rats.	2002-10	12391553
Effects of long-term acetyl-L-carnitine administration in rats: I. increased dopamine output in mesocorticolimbic areas and protection toward acute stress exposure.	2002-09	12225698
Synaptic mechanisms of inspiratory off-switching evoked by pontine pneumotaxic stimulation in cats.	2002-09	12204298
Severe impairment of NMDA receptor function in mice carrying targeted point mutations in the glycine binding site results in drug-resistant nonhabituating hyperactivity.	2002-08-01	12151550
NMDA receptor antagonists impair motor performance in immature rats.	2002-08	12172689
N-Methyl-D-aspartate receptor blockade by dizocilpine prevents stress-induced sudden death in cardiomyopathic hamsters.	2002-07-19	12106681
Effects of kainic acid on rat body temperature: unmasking by dizocilpine.	2002-07	12213256
Characterization of the discriminative stimulus effects of N-methyl- D-aspartate ligands under different ethanol training conditions in the cynomolgus monkey ( Macaca fascicularis).	2002-07	12122485
Low doses of dizocilpine block the development and subsequent expression of locomotor sensitization to nicotine in rats.	2002-06	12073164
Discriminative stimulus effects of ethanol in C57BL/6J and DBA/2J inbred mice.	2002-06	12068241
NMDA receptor involvement in imipramine withdrawal-associated effects on swim stress, GABA levels and NMDA receptor binding in rat hippocampus.	2002-05-24	12020747
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.	2002-05	12045473
Involvement of dopaminergic system in the nucleus accumbens in the discriminative stimulus effects of phencyclidine.	2002-05	12015202
Relative reinforcing strength of three N-methyl-D-aspartate antagonists with different onsets of action.	2002-05	11961074
Endogenous excitatory amino acid neurotransmission regulates thyroid-stimulating hormone and thyroid hormone secretion in conscious freely moving male rats.	2002-04	12108519
Behavioral effects of MK-801 on reserpine-treated mice.	2002-04	11999899
Protection of methylmercury effects on the in vivo dopamine release by NMDA receptor antagonists and nitric oxide synthase inhibitors.	2002-04	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.	2002-04	11907185
Nitric-oxide-synthase-mediated cyclic guanosine monophosphate production in neonatal rat cerebellar prisms is resistant to calcineurin inhibition.	2002-03-29	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?	2002-03-08	11852186
Dizocilpine inhibits amphetamine-induced formation of nitric oxide and amphetamine-induced release of amino acids and acetylcholine in the rat brain.	2002-03	11958521
Cerebral glucose utilization in transgenic mice overexpressing heat shock protein 70 is altered by dizocilpine.	2002-03	11918653
Enhancement of the discriminative stimulus effects of phencyclidine by the tetracycline antibiotics doxycycline and minocycline in rats.	2002-03	11889503
Potentiation of nuclear activator protein-1 DNA binding following brief exposure to N-methyl-D-aspartate in immature cultured rat hippocampal neurons.	2002-02-15	11835319
MK801 suppresses the L-DOPA-induced increase of glutamate in striatum of hemi-Parkinson rats.	2002-02-01	11814417
Ammonia-induced extracellular accumulation of taurine in the rat striatum in vivo: role of ionotropic glutamate receptors.	2002-02	11926274
Physiological properties of late inspiratory neurons and their possible involvement in inspiratory off-switching in cats.	2002-02	11826069
Sexually dimorphic effects of morphine and MK-801: sex steroid-dependent and -independent mechanisms.	2002-02	11796656
Prenatal choline supplementation protects against postnatal neurotoxicity.	2002-01-01	11756524
Extradural compression of sensorimotor cortex: a useful model for studies on ischemic brain damage and neuroprotection.	2002-01	11852980
Melanin concentrating hormone increase hippocampal synaptic transmission in the rat.	2002-01	11814630
Changes in dopaminergic and glutamatergic excitatory mechanisms of micturition reflex after middle cerebral artery occlusion in conscious rats.	2002-01	11771945
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
Possible mechanism of anticonvulsant effect of ketamine in mice.	2001-10	11883507
[Ability of novel non-competitive glutamate receptor blocking agents to weaken motor disorders in animals].	2001-09	11763540
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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:16 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:16 GMT 2025`
Record UNII	7PY8KH681I
Record Status	`Validated (UNII)`
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Name

Type

Language

DIZOCILPINE

Official Name

English

MK-801

Preferred Name

English

Dizocilpine [WHO-DD]

Common Name

English

DIZOCILPINE [MI]

Common Name

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

Classification Tree Code System Code

EPA PESTICIDE CODE

605204