Dizocilpine | CAS#77086-21-6 | NMDA receptor antagonist

MedKoo Cat#: 317145 | Name: Dizocilpine free base

Description:

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

Dizocilpine is a potent and selective non-competitive NMDA receptor antagonist. Dizocilpine acts as an open channel blocker of the NMDA receptor operated ion channel. It is a drug implicated in central nervous system with anesthetic and anticonvulsant effect.

Chemical Structure

Dizocilpine free base

CAS#77086-21-6 (free base)

Theoretical Analysis

MedKoo Cat#: 317145

Name: Dizocilpine free base

CAS#: 77086-21-6 (free base)

Chemical Formula: C16H15N

Exact Mass: 221.1204

Molecular Weight: 221.30

Elemental Analysis: C, 86.84; H, 6.83; N, 6.33

Price and Availability

Size	Price	Availability
25mg	USD 250.00	2 Weeks
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 1,950.00	2 Weeks
1g	USD 2,650.00	2 Weeks

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Related CAS #

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

Synonym

Dizocilpine; Dizocilpina; Dizocilpinum; MK801; MK 801; MK-801;

IUPAC/Chemical Name

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

InChi Key

LBOJYSIDWZQNJS-CVEARBPZSA-N

InChi Code

InChI=1S/C16H15N/c1-16-13-8-4-2-6-11(13)10-15(17-16)12-7-3-5-9-14(12)16/h2-9,15,17H,10H2,1H3/t15-,16+/m1/s1

SMILES Code

C[C@@]12C3=CC=CC=C3C[C@H](C4=CC=CC=C24)N1

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 (MK-801), a potent anticonvulsant, is a selective and non-competitive NMDA receptor antagonist, with a 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
	DMSO	68.0	307.27

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 221.30 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.

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Propofol can Protect Against the Impairment of Learning-memory Induced by Electroconvulsive Shock via Tau Protein Hyperphosphorylation in Depressed Rats. Chin Med Sci J. 2015 Jun;30(2):100-7. PubMed PMID: 26149001. 8: Timić Stamenić T, Joksimović S, Biawat P, Stanković T, Marković B, Cook JM, Savić MM. Negative modulation of α5 GABAA receptors in rats may partially prevent memory impairment induced by MK-801, but not amphetamine- or MK-801-elicited hyperlocomotion. J Psychopharmacol. 2015 Sep;29(9):1013-24. doi: 10.1177/0269881115590601. Epub 2015 Jun 23. PubMed PMID: 26105958. 9: Egunlusi AO, Malan SF, Joubert J. Tricycloundecane Derivatives as Potential N-Methyl-D-aspartate (NMDA) Receptor and Voltage-Gated Calcium Channel Modulators. ChemMedChem. 2015 Jul;10(7):1259-66. doi: 10.1002/cmdc.201500072. Epub 2015 May 26. PubMed PMID: 26012541. 10: Yu HC, Wu J, Zhang HX, Zhang GL, Sui J, Tong WW, Zhang XY, Nie LL, Duan JH, Zhang LR, Lv LX. Alterations of miR-132 are novel diagnostic biomarkers in peripheral blood of schizophrenia patients. Prog Neuropsychopharmacol Biol Psychiatry. 2015 Dec 3;63:23-9. doi: 10.1016/j.pnpbp.2015.05.007. Epub 2015 May 16. PubMed PMID: 25985888. 11: Yamakuni T, Kawahata I. [Pharmacological superiority of nobiletin-rich Citrus reticulata peel, a multicomponent drug, over nobiletin alone regarding anti-dementia action]. Nihon Yakurigaku Zasshi. 2015 May;145(5):229-33. doi: 10.1254/fpj.145.229. Japanese. PubMed PMID: 25958909. 12: 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. 13: Sönmez A, Sayın O, Gürgen SG, Çalişir M. Neuroprotective effects of MK-801 against traumatic brain injury in immature rats. Neurosci Lett. 2015 Jun 15;597:137-42. doi: 10.1016/j.neulet.2015.05.001. Epub 2015 May 2. PubMed PMID: 25943283. 14: Sinner B, Friedrich O, Lindner R, Bundscherer A, Graf BM. Long-term NMDA receptor inhibition affects NMDA receptor expression and alters glutamatergic activity in developing rat hippocampal neurons. Toxicology. 2015 Jul 3;333:147-55. doi: 10.1016/j.tox.2015.04.017. Epub 2015 Apr 30. PubMed PMID: 25937004. 15: Pitychoutis PM, Belmer A, Moutkine I, Adrien J, Maroteaux L. Mice Lacking the Serotonin Htr2B Receptor Gene Present an Antipsychotic-Sensitive Schizophrenic-Like Phenotype. Neuropsychopharmacology. 2015 Nov;40(12):2764-73. doi: 10.1038/npp.2015.126. Epub 2015 May 4. PubMed PMID: 25936642. 16: Larrauri JA, Burke DA, Hall BJ, Levin ED. Role of nicotinic receptors in the lateral habenula in the attenuation of amphetamine-induced prepulse inhibition deficits of the acoustic startle response in rats. Psychopharmacology (Berl). 2015 Aug;232(16):3009-17. doi: 10.1007/s00213-015-3940-z. Epub 2015 Apr 28. PubMed PMID: 25912180; PubMed Central PMCID: PMC4515155. 17: Vuckovic S, Srebro D, Savic Vujovic K, Prostran M. The antinociceptive effects of magnesium sulfate and MK-801 in visceral inflammatory pain model: The role of NO/cGMP/K(+)ATP pathway. Pharm Biol. 2015;53(11):1621-7. doi: 10.3109/13880209.2014.996821. Epub 2015 Apr 9. PubMed PMID: 25856706. 18: Roux C, Aligny C, Lesueur C, Girault V, Brunel V, Ramdani Y, Genty D, Driouich A, Laquerrière A, Marret S, Brasse-Lagnel C, Gonzalez BJ, Bekri S. NMDA receptor blockade in the developing cortex induces autophagy-mediated death of immature cortical GABAergic interneurons: An ex vivo and in vivo study in Gad67-GFP mice. 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