An NMDA receptor antagonist
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(−)-MK-801 (maleate)

Item No. 27213

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5R,10S)-10,11-dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imine, (2Z)-2-butenedioate
CAS Number
121917-57-5
Molecular Formula
C16H15N • C4H4O4
Formula Weight
337.4
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMF:PBS (pH 7.2) (1:1): 0.5 mg/mlDMSO: 20 mg/mlEthanol: 0.5 mg/ml
SMILES
[H][C@]12CC3=C(C=CC=C3)[C@](N2)(C)C4=CC=CC=C41.OC(/C=C\C(O)=O)=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $36

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    10 mg

    $68

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    25 mg

    $153

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    50 mg

    $268

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    Product Description

    (–)-MK-801 is an NMDA receptor antagonist (Ki = 43 nM for inhibition of spermine binding) and an isomer of (+)-MK-801 (Item No. 10009019).1 In vivo, (–)-MK-801 blocks generalized seizures in a mouse model of epilepsy (ED50 = 0.85 mg/kg) and increases horizontal locomotor activity in mice (ED50 = 2.71 mg/kg).2 (–)-MK-801 (0.1 mg/kg) decreases immobility time in the tail suspension and forced swim tests in a mouse model of social defeat stress, indicating antidepressant-like activity.3 (–)-MK-801 also inhibits acetylcholinesterase (AChE) with Ki values of 6.2 and 7.9 μM for electric eel and rat brain AChE, respectively.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Berger, M.L., Schweifer, A., Rebernik, P., et al. NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds. Bioorg. Med. Chem. 17(9), 3456-3462 (2009).

    2. Dravid, S.M., Erreger, K., Yuan, H., et al. Subunit-specific mechanisms and proton sensitivity of NMDA receptor channel block. J. Physiol. 581(Pt. 1), 107-128 (2007).

    3. Yang, B., Ren, Q., Ma, M., et al. Antidepressant effects of (+)-MK-801 and (−)-MK-801 in the social defeat stress model. Int. J. Neuropsychopharmacol. 19(12), pyw080 (2016).

    4. Galli, A., and Mori, F. Acetylcholinesterase inhibition and protection by dizocilpine (MK-801) enantiomers. J. Pharm. Pharmacol. 48(1), 71-76 (1996).