Dizocilpine maleate | MK-801 | CAS#77086-22-7 | 77086-21-6 | NMDA antagonist

MedKoo Cat#: 326700 | Name: Dizocilpine maleate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dizocilpine, also known as MK-801 or (+)-MK-801, is an uncompetitive antagonist of the N-Methyl-D-aspartate (NMDA) receptor. Dizocilpine blocks NMDA receptors in a use- and voltage-dependent manner, since the channel must open for the drug to bind inside it. The drug acts as a potent anti-convulsant and likely has dissociative anesthetic properties, but it is not used clinically for this purpose due to the discovery of brain lesions, called Olney's lesions (see below), in test rats. Dizocilpine is the most frequently used non-competitive NMDA receptor antagonist in animal models to mimic psychosis for experimental purposes.

Chemical Structure

Dizocilpine maleate

CAS#77086-22-7 (maleate)

Theoretical Analysis

MedKoo Cat#: 326700

Name: Dizocilpine maleate

CAS#: 77086-22-7 (maleate)

Chemical Formula: C20H19NO4

Exact Mass: 0.0000

Molecular Weight: 337.38

Elemental Analysis: C, 71.20; H, 5.68; N, 4.15; O, 18.97

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 600.00	2 Weeks
100mg	USD 950.00	2 Weeks

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Related CAS #

77086-21-6 (free base) 77086-22-7 (maleate)

Synonym

MK-801; MK 801; MK801; MK-801 maleate; Dizocilpine maleate; (+)-MK 801 Maleate; (+)-MK-801 hydrogen maleate; Dizocilpine hydrogen maleate

IUPAC/Chemical Name

(5S,10R)-5-methyl-10,11-dihydro-5H-5,10-epiminodibenzo[a,d][7]annulene maleate

InChi Key

QLTXKCWMEZIHBJ-PJGJYSAQSA-N

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+;/m1./s1

SMILES Code

C[C@]12C3=CC=CC=C3[C@@]([H])(CC4=CC=CC=C42)N1.O=C(O)/C=C\C(O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Related CAS# 77086-22-7 ( Dizocilpine maleate); 77086-21-6 ( Dizocilpine free base).

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Dizocilpine maleate (MK-801 maleate) is a potent, selective and non-competitive NMDA receptor antagonist with Kd of 37.2 nM in rat brain membranes.

In vitro activity:

These findings suggested that MK-801 administration decreased cell survival probably via the increasing GSK-3β gene expression and activity in the SH-SY5Y cells. Pre-treatments with famotidine, olanzapine, and SB 415286 prevented MK-801 induced cell death via inhibitory effects on the MK-801 induced GSK-3β activity. Reference: Chem Biol Interact. 2019 Dec 1;314:108823. https://pubmed.ncbi.nlm.nih.gov/31563592/

In vivo activity:

Open field test aimed to explore the effect of SZASD on locomotor activity in MK801-induced schizophrenia-like rats. The representative movement traces of rats in six groups are shown in Fig. 2. The results showed that MK801 has significantly increased the total distance (F = 8.738, p < 0.001) and average speed (F = 9.533, p < 0.001) of rats compared with the control group (Fig. 2B,C). Furthermore, this study investigated the anxious behavior of rats by recording the time spent in the central area (F = 2.878). MK801 remarkably reduced the time spent in the central area of rats compared with the control (p < 0.05). Reference: J Integr Neurosci. 2022 Sep 27;21(6):164. https://pubmed.ncbi.nlm.nih.gov/36424738/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	74.10
	DMF:PBS (pH 7.2) (1:9)	0.5	1.48
	DMSO	63.8	189.01
	Ethanol	12.8	37.79
	Water	8.4	24.99

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 337.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Unal G, Dokumaci AH, Ozkartal CS, Yerer MB, Aricioglu F. Famotidine has a neuroprotective effect on MK-801 induced toxicity via the Akt/GSK-3β/β-catenin signaling pathway in the SH-SY5Y cell line. Chem Biol Interact. 2019 Dec 1;314:108823. doi: 10.1016/j.cbi.2019.108823. Epub 2019 Sep 26. PMID: 31563592. 2. Massari CM, Castro AA, Dal-Cim T, Lanznaster D, Tasca CI. In vitro 6-hydroxydopamine-induced toxicity in striatal, cerebrocortical and hippocampal slices is attenuated by atorvastatin and MK-801. Toxicol In Vitro. 2016 Dec;37:162-168. doi: 10.1016/j.tiv.2016.09.015. Epub 2016 Sep 17. PMID: 27647473. 3. Liu X, Feng S, Feng Z, Ma C, He Y, Li X, Ning Y, Sun Z, Jia H. Protective Effects of Shi-Zhen-An-Shen Decoction on the Cognitive Impairment in MK801-Induced Schizophrenia Model. J Integr Neurosci. 2022 Sep 27;21(6):164. doi: 10.31083/j.jin2106164. PMID: 36424738. 4. Latuske P, von Heimendahl M, Deiana S, Wotjak CT, du Hoffmann J. Sustained MK-801 induced deficit in a novel probabilistic reversal learning task. Front Pharmacol. 2022 Oct 14;13:898548. doi: 10.3389/fphar.2022.898548. PMID: 36313373; PMCID: PMC9614101.

In vitro protocol:

In vivo protocol:

1. Liu X, Feng S, Feng Z, Ma C, He Y, Li X, Ning Y, Sun Z, Jia H. Protective Effects of Shi-Zhen-An-Shen Decoction on the Cognitive Impairment in MK801-Induced Schizophrenia Model. J Integr Neurosci. 2022 Sep 27;21(6):164. doi: 10.31083/j.jin2106164. PMID: 36424738. 2. Latuske P, von Heimendahl M, Deiana S, Wotjak CT, du Hoffmann J. Sustained MK-801 induced deficit in a novel probabilistic reversal learning task. Front Pharmacol. 2022 Oct 14;13:898548. doi: 10.3389/fphar.2022.898548. PMID: 36313373; PMCID: PMC9614101.

1: Abuhamdah RM, Hussain MD, Chazot PL, Ennaceur A. Pre-training in a radial arm maze abolished anxiety and impaired habituation in C57BL6/J mice treated with dizocilpine. Physiol Behav. 2016 Jun 15. pii: S0031-9384(16)30416-4. doi: 10.1016/j.physbeh.2016.06.017. [Epub ahead of print] PubMed PMID: 27317838. 2: Vojtechova I, Petrasek T, Hatalova H, Pistikova A, Vales K, Stuchlik A. Dizocilpine (MK-801) impairs learning in the active place avoidance task but has no effect on the performance during task/context alternation. Behav Brain Res. 2016 May 15;305:247-57. doi: 10.1016/j.bbr.2016.03.020. Epub 2016 Mar 10. PubMed PMID: 26970577. 3: Gao ZY, Yang P, Huang QJ, Xu HY. The influence of dizocilpine on the reserpine-induced behavioral and neurobiological changes in rats. Neurosci Lett. 2016 Feb 12;614:89-94. doi: 10.1016/j.neulet.2016.01.006. Epub 2016 Jan 11. PubMed PMID: 26779676. 4: Khan N, Saad A, Nurulain SM, Darras FH, Decker M, Sadek B. The dual-acting H3 receptor antagonist and AChE inhibitor UW-MD-71 dose-dependently enhances memory retrieval and reverses dizocilpine-induced memory impairment in rats. Behav Brain Res. 2016 Jan 15;297:155-64. doi: 10.1016/j.bbr.2015.10.022. Epub 2015 Oct 20. PubMed PMID: 26467607. 5: Bloch K, Gil-Ad I, Tarasenko I, Vanichkin A, Taler M, Hornfeld SH, Vardi P, Weizman A. Intracranial pancreatic islet transplantation increases islet hormone expression in the rat brain and attenuates behavioral dysfunctions induced by MK-801 (dizocilpine). Horm Behav. 2015 Jun;72:1-11. doi: 10.1016/j.yhbeh.2015.04.019. Epub 2015 May 2. PubMed PMID: 25943974. 6: Yoshimi N, Futamura T, Hashimoto K. Improvement of dizocilpine-induced social recognition deficits in mice by brexpiprazole, a novel serotonin-dopamine activity modulator. Eur Neuropsychopharmacol. 2015 Mar;25(3):356-64. doi: 10.1016/j.euroneuro.2014.12.014. Epub 2015 Jan 5. PubMed PMID: 25600995. 7: Allen RM, Mandt BH, Jaskunas J, Hackley A, Shickedanz A, Bergkamp D. Continuous exposure to dizocilpine facilitates the acquisition and escalation of cocaine consumption in male Sprague-Dawley rats. Drug Alcohol Depend. 2015 Feb 1;147:137-43. doi: 10.1016/j.drugalcdep.2014.11.027. Epub 2014 Dec 9. PubMed PMID: 25523326. 8: Srejovic I, Jakovljevic V, Zivkovic V, Barudzic N, Radovanovic A, Stanojlovic O, Djuric DM. The effects of the modulation of NMDA receptors by homocysteine thiolactone and dizocilpine on cardiodynamics and oxidative stress in isolated rat heart. Mol Cell Biochem. 2015 Mar;401(1-2):97-105. doi: 10.1007/s11010-014-2296-8. Epub 2014 Dec 3. PubMed PMID: 25467376. 9: Lobellová V, Brichtová E, Petrásek T, Valeš K, Stuchlík A. Higher doses of (+)MK-801 (dizocilpine) induced mortality and procedural but not cognitive deficits in delayed testing in the active place avoidance with reversal on the Carousel. Physiol Res. 2015;64(2):269-75. Epub 2014 Oct 15. PubMed PMID: 25317686. 10: Burke DA, Heshmati P, Kholdebarin E, Levin ED. Decreasing nicotinic receptor activity and the spatial learning impairment caused by the NMDA glutamate antagonist dizocilpine in rats. Eur J Pharmacol. 2014 Oct 15;741:132-9. doi: 10.1016/j.ejphar.2014.07.030. Epub 2014 Jul 24. PubMed PMID: 25064338; PubMed Central PMCID: PMC4184962. 11: Rejdak K, Nieoczym D, Czuczwar M, Kiś J, Wlaź P, Turski WA. Orphenadrine-induced convulsive status epilepticus in rats responds to the NMDA antagonist dizocilpine. Pharmacol Rep. 2014 Jun;66(3):399-403. doi: 10.1016/j.pharep.2013.12.007. Epub 2014 Apr 2. PubMed PMID: 24905515. 12: Allen RM. Continuous exposure to dizocilpine facilitates escalation of cocaine consumption in male Sprague-Dawley rats. Drug Alcohol Depend. 2014 Jan 1;134:38-43. doi: 10.1016/j.drugalcdep.2013.09.005. Epub 2013 Sep 14. PubMed PMID: 24103127; PubMed Central PMCID: PMC3865177. 13: Zangrando J, Carvalheira R, Labbate G, Medeiros P, Longo BM, Melo-Thomas L, Silva RC. Atypical antipsychotic olanzapine reversed deficit on prepulse inhibition of the acoustic startle reflex produced by microinjection of dizocilpine (MK-801) into the inferior colliculus in rats. Behav Brain Res. 2013 Nov 15;257:77-82. doi: 10.1016/j.bbr.2013.09.018. Epub 2013 Sep 14. PubMed PMID: 24045065. 14: Han D, Xu L, Xiao H, Prado Schmidt GC, Shi S. Dizocilpine reduces head diameter of dendritic spines in the hippocampus of adolescent rats. Psychiatry Res. 2013 Nov 30;210(1):351-6. doi: 10.1016/j.psychres.2013.04.025. Epub 2013 Jun 6. PubMed PMID: 23747234. 15: Liu C, Min S, Wei K, Liu D, Dong J, Luo J, Li P, Liu XB. Effects of propofol and dizocilpine maleate on the cognitive abilities and the hyperphosphorylation of Tau protein of rats after the electroconvulsive therapy. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 2012 Aug;34(4):324-9. doi: 10.3881/j.issn.1000-503X.2012.04.003. PubMed PMID: 22954112. 16: Galizio M, Deal M, Hawkey A, April B. Working memory in the odor span task: effects of chlordiazepoxide, dizocilpine (MK801), morphine, and scopolamine. Psychopharmacology (Berl). 2013 Jan;225(2):397-406. doi: 10.1007/s00213-012-2825-7. Epub 2012 Aug 24. PubMed PMID: 22918519; PubMed Central PMCID: PMC3529754. 17: Chen Y, Evola M, Young AM. Memantine and dizocilpine interactions with antinociceptive or discriminative stimulus effects of morphine in rats after acute or chronic treatment with morphine. Psychopharmacology (Berl). 2013 Jan;225(1):187-99. doi: 10.1007/s00213-012-2807-9. Epub 2012 Aug 4. PubMed PMID: 22864944; PubMed Central PMCID: PMC3777440. 18: Rezvani AH, Cauley MC, Johnson EC, Gatto GJ, Levin ED. Effects of AZD3480, a neuronal nicotinic acetylcholine receptor agonist, and donepezil on dizocilpine-induced attentional impairment in rats. Psychopharmacology (Berl). 2012 Oct;223(3):251-8. doi: 10.1007/s00213-012-2712-2. Epub 2012 Apr 20. PubMed PMID: 22526540. 19: Larrauri JA, Levin ED. Differential effects of the antidepressant mirtazapine on amphetamine- and dizocilpine-induced PPI deficits. Pharmacol Biochem Behav. 2012 Jul;102(1):82-7. doi: 10.1016/j.pbb.2012.03.010. Epub 2012 Mar 25. PubMed PMID: 22469866. 20: Ferenz KB, Gast RE, Rose K, Finger IE, Hasche A, Krieglstein J. Nerve growth factor and brain-derived neurotrophic factor but not granulocyte colony-stimulating factor, nimodipine and dizocilpine, require ATP for neuroprotective activity after oxygen-glucose deprivation of primary neurons. Brain Res. 2012 Apr 11;1448:20-6. doi: 10.1016/j.brainres.2012.02.016. Epub 2012 Feb 13. PubMed PMID: 22386494.