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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
[3H]acetycholine release in rat striatal slices is not subject to dopamine heteroreceptor supersensitivity 30 months after 6-hydroxydopamine lesion of the substantia nigra.
2001 Apr
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
N-methyl-D-aspartate receptor antagonists potentiate the antinociceptive effects of morphine in squirrel monkeys.
2001 Jul
Two distinct oscillatory states determined by the NMDA receptor in rat inferior olive.
2001 Jul 1
Excitatory mechanisms in neuroleptic-induced vacuous chewing movements (VCMs): possible involvement of calcium and nitric oxide.
2001 Jun
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
Microdialysates of amines and metabolites from core nucleus accumbens of freely moving rats are altered by dizocilpine.
2001 May 25
Possible mechanism of anticonvulsant effect of ketamine in mice.
2001 Oct
Delayed sclerosis, neuroprotection, and limbic epileptogenesis after status epilepticus in the rat.
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
Sexually dimorphic effects of morphine and MK-801: sex steroid-dependent and -independent mechanisms.
2002 Feb
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
Prenatal choline supplementation protects against postnatal neurotoxicity.
2002 Jan 1
N-Methyl-D-aspartate receptor blockade by dizocilpine prevents stress-induced sudden death in cardiomyopathic hamsters.
2002 Jul 19
Cerebral glucose utilization in transgenic mice overexpressing heat shock protein 70 is altered by dizocilpine.
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
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
Differential effects of direct and indirect dopamine agonists on prepulse inhibition: a study in D1 and D2 receptor knock-out mice.
2002 Nov 1
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)
Record Version
  • Download
Name Type Language
DIZOCILPINE
HSDB   INN   MI   WHO-DD  
INN  
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
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
WIKIPEDIA Designer-drugs-Dizocilpine
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
WIKIPEDIA NMDA receptor antagonist
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
NCI_THESAURUS C264
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID3048447
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY
EVMPD
SUB06341MIG
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY
PUBCHEM
180081
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY
HSDB
7641
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY
FDA UNII
7PY8KH681I
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY
NCI_THESAURUS
C65450
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY
CHEBI
176788
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY
CHEBI
34725
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY
MERCK INDEX
m4700
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL284237
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY
CAS
77086-21-6
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY
SMS_ID
100000081843
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY
INN
6320
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY
WIKIPEDIA
DIZOCILPINE
Created by admin on Mon Mar 31 17:58:16 GMT 2025 , Edited by admin on Mon Mar 31 17:58:16 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY