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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
Low doses of N-methyl-D-aspartate antagonists in superficial laminae of medulla oblongata facilitate wind-up of convergent neurones.
2001
Generalisation of ethanol with drug mixtures containing a positive modulator of the GABA(A) receptor and an NMDA antagonist.
2001
Ethanol enhances naloxone sensitization and disrupts morphine discrimination--comparison to dizocilpine and pentobarbital: explanation of enhancing acute and attenuating chronic effects.
2001 Aug
Memantine, but not dizocilpine, ameliorates cognitive deficits in adult rats withdrawn from chronic ingestion of alcohol.
2001 Aug 17
NMDA antagonists produce site-selective impairment of accuracy in a delayed nonmatch-to-sample task in rats.
2001 Dec
Comparative studies on the memory-enhancing actions of captopril and losartan in mice using inhibitory shock avoidance paradigm.
2001 Feb
Uncompetitive antagonists of the N-methyl-D-aspartate (NMDA) receptors alter the mRNA expression of proteins associated with the NMDA receptor complex.
2001 Feb
Effects of the 5-HT(6) receptor antagonist Ro 04-6790 on learning consolidation.
2001 Jan 8
Sensitization of prepulse inhibition deficits by repeated administration of dizocilpine.
2001 Jul
Comparison of apomorphine, amphetamine and dizocilpine disruptions of prepulse inhibition in inbred and outbred mice strains.
2001 Jul 13
Startle and sensorimotor gating in rats lacking CCK-A receptors.
2001 Jun
A discriminative two-lever test of dizocilpine's ability to reinstate ethanol-seeking behavior.
2001 Jun 22
Could the 5-HT1B receptor inverse agonism affect learning consolidation?
2001 Mar
Effects of competitive and non-competitive NMDA receptor antagonists on dopamine output in the shell and core subdivisions of the nucleus accumbens.
2001 Mar
Dizocilpine but not ketamine reduces the volume of ischaemic damage after acute subdural haematoma in the rat.
2001 May
Glufosinate ammonium induces convulsion through N-methyl-D-aspartate receptors in mice.
2001 May 18
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
Gacyclidine: a new neuroprotective agent acting at the N-methyl-D-aspartate receptor.
2001 Summer
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
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
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
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
Possible involvement of tachykinin NK(1) and NMDA receptors in histamine-induced hyperalgesia in mice.
2002 Jan 2
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
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
NMDA receptor involvement in imipramine withdrawal-associated effects on swim stress, GABA levels and NMDA receptor binding in rat hippocampus.
2002 May 24
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:28:23 GMT 2023
Edited
by admin
on Fri Dec 15 15:28:23 GMT 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 Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
WIKIPEDIA Designer-drugs-Dizocilpine
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
WIKIPEDIA NMDA receptor antagonist
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
NCI_THESAURUS C264
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID3048447
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY
EVMPD
SUB06341MIG
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY
PUBCHEM
180081
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY
HSDB
7641
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY
FDA UNII
7PY8KH681I
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY
NCI_THESAURUS
C65450
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY
CHEBI
176788
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY
CHEBI
34725
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY
MERCK INDEX
m4700
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL284237
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY
CAS
77086-21-6
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY
SMS_ID
100000081843
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY
INN
6320
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY
WIKIPEDIA
DIZOCILPINE
Created by admin on Fri Dec 15 15:28:23 GMT 2023 , Edited by admin on Fri Dec 15 15:28:23 GMT 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY