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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 of DIZOCILPINE

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

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
Low doses of N-methyl-D-aspartate antagonists in superficial laminae of medulla oblongata facilitate wind-up of convergent neurones.
2001
Long-term behavioral and neurodegenerative effects of perinatal phencyclidine administration: implications for schizophrenia.
2001
Estrogen increases prepulse inhibition of acoustic startle in rats.
2001 Aug 3
NMDA antagonists produce site-selective impairment of accuracy in a delayed nonmatch-to-sample task in rats.
2001 Dec
beta-Adrenoceptor blockade enhances the anticonvulsant effect of glutamate receptor antagonists against maximal electroshock.
2001 Nov 16
Influence of neurosteroids on the development of rapid tolerance to ethanol in mice.
2001 Nov 16
Phenobarbital and dizocilpine can block methamphetamine-induced neurotoxicity in mice by mechanisms that are independent of thermoregulation.
2001 Nov 16
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
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
Acamprosate is neuroprotective against glutamate-induced excitotoxicity when enhanced by ethanol withdrawal in neocortical cultures of fetal rat brain.
2001 Sep
The NMDA receptor complex: a promising target for novel antiepileptic strategies.
2001 Sep
Calcitonin gene-related peptide-mediated increase in K(+)-induced [(3)H]-dopamine release from rat caudal striatal slices.
2001 Sep 14
Absence of MK801-induced inspiratory prolongation in chronically hypoxic rats.
2001 Sep 28
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
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
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
Possible involvement of tachykinin NK(1) and NMDA receptors in histamine-induced hyperalgesia in mice.
2002 Jan 2
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
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
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
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
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:58:16 UTC 2023
Edited
by admin
on Wed Jul 05 22:58:16 UTC 2023
Record UNII
7PY8KH681I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIZOCILPINE
HSDB   INN   MI   WHO-DD  
INN  
Official Name English
Dizocilpine [WHO-DD]
Common 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
Classification Tree Code System Code
EPA PESTICIDE CODE 605204
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
WIKIPEDIA Designer-drugs-Dizocilpine
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
WIKIPEDIA NMDA receptor antagonist
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
NCI_THESAURUS C264
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID3048447
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY
EVMPD
SUB06341MIG
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY
PUBCHEM
180081
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY
HSDB
7641
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY
FDA UNII
7PY8KH681I
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY
NCI_THESAURUS
C65450
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY
CHEBI
176788
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY
CHEBI
34725
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY
MERCK INDEX
M4700
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL284237
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY
CAS
77086-21-6
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY
SMS_ID
100000081843
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY
INN
6320
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY
WIKIPEDIA
DIZOCILPINE
Created by admin on Wed Jul 05 22:58:16 UTC 2023 , Edited by admin on Wed Jul 05 22:58:16 UTC 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY