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M108

Sigma-Aldrich

(−)-MK-801 hydrogen maleate

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C16H15N · C4H4O4
CAS Number:
77086-19-2
Molecular Weight:
337.37
MDL number:
MFCD00082466
UNSPSC Code:
12352200
PubChem Substance ID:
24277961

Assay

≥98% (HPLC)

form

solid

optical activity

[α]25/D −117.7°, c = 1 in methanol(lit.)

color

white

solubility

DMSO: >20 mg/mL

storage temp.

room temp

SMILES string

[H]\C(=C(/[H])C(O)=O)C(O)=O.[H][C@@]12Cc3ccccc3[C@@](C)(N1)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+;/m0./s1

InChI key

QLTXKCWMEZIHBJ-FWHYOZOBSA-N

Gene Information

human ... GRIN1(2902) , GRIN2C(2905) , GRIN2D(2906) , GRIN3A(116443) , GRIN3B(116444) , GRINA(2907)
mouse ... GRIN1(14810) , GRIN2C(14813) , GRIN2D(14814) , GRIN3A(242443) , GRIN3B(170483) , GRINA(66168)
rat ... GRIN1(24408) , GRIN2C(24411) , GRIN2D(24412) , GRIN3A(191573) , GRIN3B(170796) , GRINA(266668)

General description

(-)-MK-801 hydrogen maleate is a less potent stereoisomer of (+)-MK-801.

Biochem/physiol Actions

Less active enantiomer of (+)-MK-801 hydrogen maleate
MK-801 functions as a selective non-competitive N-methyl-D-aspartate (NMDA) receptor antagonist.

Storage Class Code

13 - Non Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tianwen Huang et al.
The Journal of biological chemistry, 294(21), 8617-8629 (2019-04-11)
We previously reported that the cell cycle-related cyclin-dependent kinase 4-retinoblastoma (RB) transcriptional corepressor pathway is essential for stroke-induced cell death both in vitro and in vivo However, how this signaling pathway induces cell death is unclear. Previously, we found that
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)
E H Wong et al.
Proceedings of the National Academy of Sciences of the United States of America, 83(18), 7104-7108 (1986-09-01)
The compound MK-801 [(+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d] cyclohepten-5,10-imine maleate)] is a potent anticonvulsant that is active after oral administration and whose mechanism of action is unknown. We have detected high-affinity (Kd = 37.2 +/- 2.7 nM) binding sites for [3H]MK-801 in rat brain
Antidepressant Effects of (+)-MK-801 and (-)-MK-801 in the Social Defeat Stress Model.
Yang B
The International Journal of Neuropsychopharmacology, 19(12) (2016)
J Ma et al.
British journal of pharmacology, 124(4), 756-762 (1998-08-05)
1. Excitotoxic and apoptotic mechanisms have been implicated in the pathophysiology of cerebral ischaemia. Both MK-801, an NMDA receptor antagonist, or peptide inhibitors of the caspase family (z-VAD.FMK and z-DEVD.FMK), protect mouse brain from ischaemic cell damage. In this study
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