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
Low doses of N-methyl-D-aspartate antagonists in superficial laminae of medulla oblongata facilitate wind-up of convergent neurones.	2001	11731106
Generalisation of ethanol with drug mixtures containing a positive modulator of the GABA(A) receptor and an NMDA antagonist.	2001	11077078
[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	11330335
NMDA antagonists produce site-selective impairment of accuracy in a delayed nonmatch-to-sample task in rats.	2001 Dec	11747896
Comparative studies on the memory-enhancing actions of captopril and losartan in mice using inhibitory shock avoidance paradigm.	2001 Feb	11346312
N-methyl-D-aspartate receptor antagonists potentiate the antinociceptive effects of morphine in squirrel monkeys.	2001 Jul	11408554
Two distinct oscillatory states determined by the NMDA receptor in rat inferior olive.	2001 Jul 1	11432997
Excitatory mechanisms in neuroleptic-induced vacuous chewing movements (VCMs): possible involvement of calcium and nitric oxide.	2001 Jun	11485057
Dizocilpine but not ketamine reduces the volume of ischaemic damage after acute subdural haematoma in the rat.	2001 May	11350471
Glufosinate ammonium induces convulsion through N-methyl-D-aspartate receptors in mice.	2001 May 18	11335070
Microdialysates of amines and metabolites from core nucleus accumbens of freely moving rats are altered by dizocilpine.	2001 May 25	11376600
Possible mechanism of anticonvulsant effect of ketamine in mice.	2001 Oct	11883507
Delayed sclerosis, neuroprotection, and limbic epileptogenesis after status epilepticus in the rat.	2002	12121301
Endogenous excitatory amino acid neurotransmission regulates thyroid-stimulating hormone and thyroid hormone secretion in conscious freely moving male rats.	2002 Apr	12108519
Protection of methylmercury effects on the in vivo dopamine release by NMDA receptor antagonists and nitric oxide synthase inhibitors.	2002 Apr	11985818
Sexually dimorphic effects of morphine and MK-801: sex steroid-dependent and -independent mechanisms.	2002 Feb	11796656
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
Prenatal choline supplementation protects against postnatal neurotoxicity.	2002 Jan 1	11756524
N-Methyl-D-aspartate receptor blockade by dizocilpine prevents stress-induced sudden death in cardiomyopathic hamsters.	2002 Jul 19	12106681
Cerebral glucose utilization in transgenic mice overexpressing heat shock protein 70 is altered by dizocilpine.	2002 Mar	11918653
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
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
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

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

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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