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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
Pricing and availability is not currently available.

Quality Level

100

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.[1]

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.[2][1]

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

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Certificates of Analysis (COA)

Lot/Batch Number
022M4606V
059K46191
059K4619
026K46043
026K46042

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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
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
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)
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
Emil Carlsson et al.
Investigative ophthalmology & visual science, 61(2), 9-9 (2020-02-13)
Variant B precursor cysteine protease inhibitor cystatin C, a known recessive risk factor for developing exudative age-related macular degeneration (AMD), presents altered intracellular trafficking and reduced secretion from retinal pigment epithelial (RPE) cells. Because cystatin C inhibits multiple extracellular matrix
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