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M107

Sigma-Aldrich

(+)-MK-801 hydrogen maleate

powder

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Synonym(s):
(5S,10R)-(+)-5-Methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine hydrogen maleate, Dizocilpine hydrogen maleate
Empirical Formula (Hill Notation):
C16H15N · C4H4O4
CAS Number:
77086-22-7
Molecular Weight:
337.37
EC Number:
278-614-5
MDL number:
MFCD00082465
UNSPSC Code:
12352209
PubChem Substance ID:
24277988
NACRES:
NA.32

form

powder

Quality Level

100

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

Gene Information

human ... GRIN1(2902) , GRIN2A(2903) , GRIN2B(2904) , GRIN2C(2905) , GRIN2D(2906) , GRIN3A(116443) , GRIN3B(116444) , GRINA(2907)
mouse ... GRIN1(14810) , GRIN2A(14811) , GRIN2B(14812) , GRIN2C(14813) , GRIN2D(14814) , GRIN3A(242443) , GRIN3B(170483) , GRINA(66168)
rat ... GRIN1(24408) , GRIN2A(24409) , GRIN2B(24410) , GRIN2C(24411) , GRIN2D(24412) , GRIN3A(191573) , GRIN3B(170796) , GRINA(266668)

General description

(+)-MK-801 hydrogen maleate is a highly potent and selective non-competitive NMDA glutamate receptor antagonist that acts at the NMDA receptor-operated ion channel as an open channel blocker. Neurons are depolarized when MK-801 binds to the Glu (40 Glu) receptor (NMDA receptor- ion channel complex) at two sites. 40 Glu is the brain′s primary excitatory neurotransmitter. MK-801 attaches to the ion channel at the binding site PCP of the receptor. Receptor blockade occurs in a voltage-dependent manner. It also known as dizocilpine hydrogen maleate is an effective anticonvulsant with both anxiolytic and sympathomimetic properties.(+)-MK-801 hydrogen maleate stimulates locomotion in monoamine-depleted mice.

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.

Biochem/physiol Actions

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Chia-Hsueh Lee et al.
Nature, 511(7508), 191-197 (2014-07-11)
N-methyl-d-aspartate (NMDA) receptors are Hebbian-like coincidence detectors, requiring binding of glycine and glutamate in combination with the relief of voltage-dependent magnesium block to open an ion conductive pore across the membrane bilayer. Despite the importance of the NMDA receptor in
Management of delayed edema formation after fibrinolytic therapy for intracerebral hematomas: preliminary experimental data.
Rohde V
Acta Neurochirurgica. Supplement, 105, 101-104 (2008)
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
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
The NMDA antagonist MK-801 causes marked locomotor stimulation in monoamine-depleted mice.
Carlsson M and Carlsson A
Journal of Neural Transmission. General Section, 75(3), 221-226 (1989)
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