All Photos(1)

M107

Sigma-Aldrich

(+)-MK-801 hydrogen maleate

powder

Synonym(s):
Dizocilpine hydrogen maleate, (5S,10R)-(+)-5-Methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine hydrogen maleate
Empirical Formula (Hill Notation):
C16H15N · C4H4O4
CAS Number:
Molecular Weight:
337.37
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

form

powder

optical activity

[α]25/D +117°, c = 1 in methanol(lit.)

color

white

solubility

DMSO: >20 mg/mL
H2O: 6 mg/mL
0.1 M HCl: soluble
ethanol: soluble

SMILES string

[H]\C(=C(/[H])C(O)=O)C(O)=O.C[C@]12N[C@H](Cc3ccccc13)c4ccccc24

InChI

1S/C16H15N.C4H4O4/c1-16-13-8-4-2-6-11(13)10-15(17-16)12-7-3-5-9-14(12)16;5-3(6)1-2-4(7)8/h2-9,15,17H,10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t15-,16+;/m1./s1

InChI key

QLTXKCWMEZIHBJ-PJGJYSAQSA-N

General description

MK-801 [(+)-5-methyl-10,11-dihydroxy-5H-dibenzo(a,d)cyclohepten-5,10-imine] also known as dizocilpine hydrogen maleate is an effective anticonvulsant with both anxiolytic and sympathomimetic properties.

Application

(+)-MK-801 hydrogen maleate has been used in following experimental studies:
It is injected to mice to study the effect of systemic administration of CIQ [(3-chlorophenyl) (6, 7-dimethoxy-1-((4-methoxyphenoxy) methyl)-3, 4-dihydroisoquinolin-2(1H)-yl)methanone] on schizophrenia-like behaviours stimulated by MK-801.
It has been used to block the NMDA (N-methyl-D-aspartate) receptor-mediated rtPA (recombinant tissue plasminogen activator)-enhanced excitotoxic pathway.
It is injected in varied doses to study behavioral performance altering effects of MK-801 in zebrafish (Danio rerio).
It is used as a NMDA receptor antagonist to study 3-OH-GA-induced neuronal damage via NMDA receptors.

Packaging

25 mg in poly bottle
5 mg in glass bottle
50, 250 mg in glass bottle

Biochem/physiol Actions

MK-801 [(+)-5-methyl-10, 11-dihydroxy-5H-dibenzo (a, d) cyclohepten-5, 10-imine] functions as a selective non-competitive N-methyl-D-aspartate (NMDA) receptor antagonist and stimulates locomotion in monoamine-depleted mice. Experimental study shows that MK-801, influence circling behavior in a direction-specific manner, modify swimming activity and place preference in zebrafish. Acute injection of MK-801, dose dependently, enhances extracellular acetylcholine (ACh) release in the rat parietal cortex. For intracerebral hematomas, MK-801 might act as a potent supplement to reduce delayed edema after recombinant tissue plasminogen activator (rtPA) clot lysis. MK-801 functions as an antidepressant in the social defeat stress model, but it doesn′t have long-lasting effect.
Highly potent and selective non-competitive NMDA glutamate receptor antagonist that acts at the NMDA receptor-operated ion channel as an open channel blocker. Inhibits behavioral sensitization to psychostimulants and ethanol.

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Elizabeth K Ruzzo et al.
Cell, 178(4), 850-866 (2019-08-10)
We performed a comprehensive assessment of rare inherited variation in autism spectrum disorder (ASD) by analyzing whole-genome sequences of 2,308 individuals from families with multiple affected children. We implicate 69 genes in ASD risk, including 24 passing genome-wide Bonferroni correction and...
Management of delayed edema formation after fibrinolytic therapy for intracerebral hematomas: preliminary experimental data.
Rohde V
Acta Neurochirurgica. Supplement, 105, 101-104 (2008)
Gabrielle Girardeau et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 34(15), 5176-5183 (2014-04-11)
Hippocampal sharp wave-ripples (SPW-Rs) and associated place-cell reactivations are crucial for spatial memory consolidation during sleep and rest. However, it remains unclear how learning and consolidation requirements influence and regulate subsequent SPW-R activity. Indeed, SPW-R activity has been observed not...
MK-801 increases endogenous acetylcholine release in the rat parietal cortex: a study using brain microdialysis.
Hasegawa M
Neuroscience Letters, 150(1), 53-56 (1993)
Effects of dizocilpine (MK-801) on circling behavior, swimming activity, and place preference in zebrafish (Danio rerio).
Swain HA
Neurotoxicology and Teratology, 26(6), 725-729 (2004)

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