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M107

(+)-MK-801 hydrogen maleate

NMDA glutamate receptor antagonist, powder

Synonym(s):

(5S,10R)-(+)-5-Methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine hydrogen maleate, Dizocilpine hydrogen maleate

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About This Item

Empirical Formula (Hill Notation):
C16H15N · C4H4O4
CAS Number:
77086-22-7
Molecular Weight:
337.37
NACRES:
NA.32
PubChem Substance ID:
24277988
UNSPSC Code:
12352209
EC Number:
278-614-5
MDL number:
MFCD00082465
Form:
powder
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Product Name

(+)-MK-801 hydrogen maleate, powder

form

powder

Quality Segment

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

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.

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

Eyeshields, Gloves, type N95 (US)

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