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MedKoo Cat#: 463847 | Name: Cuprizone
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Description:

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

Cuprizone is an inducer of demyelination and motor dysfunction via upregulation of IGF-1.

Chemical Structure

Cuprizone
Cuprizone
CAS#370-81-0

Theoretical Analysis

MedKoo Cat#: 463847

Name: Cuprizone

CAS#: 370-81-0

Chemical Formula: C14H22N4O2

Exact Mass: 278.1743

Molecular Weight: 278.36

Elemental Analysis: C, 60.41; H, 7.97; N, 20.13; O, 11.50

Price and Availability

Size Price Availability Quantity
1g USD 90.00 Ready to ship
2g USD 110.00 Ready to ship
5g USD 220.00 Ready to ship
10g USD 350.00 Ready to ship
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Related CAS #
No Data
Synonym
Cuprizone; Cuprizane; Cuprizon; Oxalic acid bis(cyclohexylidenehydrazide); NSC-4283; NSC4283; NSC 4283;
IUPAC/Chemical Name
N'1,N'2-dicyclohexylideneoxalohydrazide
InChi Key
DSRJIHMZAQEUJV-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H22N4O2/c19-13(17-15-11-7-3-1-4-8-11)14(20)18-16-12-9-5-2-6-10-12/h1-10H2,(H,17,19)(H,18,20)
SMILES Code
O=C(C(N/N=C1CCCCC/1)=O)N/N=C2CCCCC\2
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
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
Certificate of Analysis
View CoA: current batch, Lot#A24M09B26
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 278.36 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.

Recalculate based on batch purity %
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
1: Bagheri SM, Maghsoudi MJ, Yadegari M. Preventive Effect of Ferula asafoetida Oleo Gum Resin on Histopathology in Cuprizone-Induced Demyelination Mice. Int J Prev Med. 2020 Nov 26;11:179. doi: 10.4103/ijpvm.IJPVM_108_19. PMID: 33456735; PMCID: PMC7804879. 2: Sy M, Brandt AU, Lee SU, Newton BL, Pawling J, Golzar A, Rahman AMA, Yu Z, Cooper G, Scheel M, Paul F, Dennis JW, Demetriou M. N-acetylglucosamine drives myelination by triggering oligodendrocyte precursor cell differentiation. J Biol Chem. 2020 Dec 18;295(51):17413-17424. doi: 10.1074/jbc.RA120.015595. PMID: 33453988; PMCID: PMC7762951. 3: Goldman SA, Mariani JN, Madsen PM. Glial progenitor cell-based repair of the dysmyelinated brain: Progression to the clinic. Semin Cell Dev Biol. 2021 Jan 4:S1084-9521(20)30198-1. doi: 10.1016/j.semcdb.2020.12.004. Epub ahead of print. PMID: 33414060. 4: Lee DW, Kwon JI, Woo CW, Heo H, Kim KW, Woo DC, Kim JK, Lee DH. In Vivo Measurement of Neurochemical Abnormalities in the Hippocampus in a Rat Model of Cuprizone-Induced Demyelination. Diagnostics (Basel). 2020 Dec 30;11(1):E45. doi: 10.3390/diagnostics11010045. PMID: 33396601. 5: Liu Y, Fan H, Li X, Liu J, Qu X, Wu X, Liu M, Liu Z, Yao R. Trpv4 regulates Nlrp3 inflammasome via SIRT1/PGC-1α pathway in a cuprizone-induced mouse model of demyelination. Exp Neurol. 2020 Dec 31;337:113593. doi: 10.1016/j.expneurol.2020.113593. Epub ahead of print. PMID: 33387462. 6: Lee J, Villarreal OD, Chen X, Zandee S, Young YK, Torok C, Lamarche-Vane N, Prat A, Rivest S, Gosselin D, Richard S. QUAKING Regulates Microexon Alternative Splicing of the Rho GTPase Pathway and Controls Microglia Homeostasis. Cell Rep. 2020 Dec 29;33(13):108560. doi: 10.1016/j.celrep.2020.108560. PMID: 33378678. 7: El-Etr M, Akwa Y, Rame M, Schumacher M, Sitruk-Ware R. Nestorone® , a 19nor-progesterone derivative boosts remyelination in an animal model of demyelination. CNS Neurosci Ther. 2020 Dec 24. doi: 10.1111/cns.13538. Epub ahead of print. PMID: 33369182. 8: Ineichen BV, Zhu K, Carlström KE. Axonal mitochondria adjust in size depending on g-ratio of surrounding myelin during homeostasis and advanced remyelination. J Neurosci Res. 2020 Dec 25. doi: 10.1002/jnr.24767. Epub ahead of print. PMID: 33368634. 9: Lee DW, Heo H, Woo CW, Woo DC, Kim JK, Kim KW, Lee DH. Temporal Changes in In Vivo Glutamate Signal during Demyelination and Remyelination in the Corpus Callosum: A Glutamate-Weighted Chemical Exchange Saturation Transfer Imaging Study. Int J Mol Sci. 2020 Dec 12;21(24):9468. doi: 10.3390/ijms21249468. PMID: 33322784; PMCID: PMC7764201. 10: Auderset L, Pitman KA, Cullen CL, Pepper RE, Taylor BV, Foa L, Young KM. Low-Density Lipoprotein Receptor-Related Protein 1 (LRP1) Is a Negative Regulator of Oligodendrocyte Progenitor Cell Differentiation in the Adult Mouse Brain. Front Cell Dev Biol. 2020 Nov 13;8:564351. doi: 10.3389/fcell.2020.564351. PMID: 33282858; PMCID: PMC7691426. 11: Cisbani G, Poggini S, Laflamme N, Pons V, Tremblay MÈ, Branchi I, Rivest S. The Intellicage system provides a reproducible and standardized method to assess behavioral changes in cuprizone-induced demyelination mouse model. Behav Brain Res. 2020 Dec 3;400:113039. doi: 10.1016/j.bbr.2020.113039. Epub ahead of print. PMID: 33279637. 12: Yang L, Su Y, Guo F, Zhang H, Zhao Y, Huang Q, Xu H. Deep rTMS Mitigates Behavioral and Neuropathologic Anomalies in Cuprizone-Exposed Mice Through Reducing Microglial Proinflammatory Cytokines. Front Integr Neurosci. 2020 Nov 5;14:556839. doi: 10.3389/fnint.2020.556839. PMID: 33250722; PMCID: PMC7674917. 13: Carrete A, Padilla-Ferrer A, Simon A, Meffre D, Jafarian-Tehrani M. Effect of Etazolate upon Cuprizone-induced Demyelination In Vivo: Behavioral and Myelin Gene Analysis. Neuroscience. 2020 Nov 24:S0306-4522(20)30741-7. doi: 10.1016/j.neuroscience.2020.11.027. Epub ahead of print. PMID: 33246058. 14: Kaddatz H, Joost S, Nedelcu J, Chrzanowski U, Schmitz C, Gingele S, Gudi V, Stangel M, Zhan J, Santrau E, Greiner T, Frenz J, Müller-Hilke B, Müller M, Amor S, van der Valk P, Kipp M. Cuprizone-induced demyelination triggers a CD8-pronounced T cell recruitment. Glia. 2020 Nov 27. doi: 10.1002/glia.23937. Epub ahead of print. PMID: 33245604. 15: Khalilian B, Madadi S, Fattahi N, Abouhamzeh B. Coenzyme Q10 enhances remyelination and regulate inflammation effects of cuprizone in corpus callosum of chronic model of multiple sclerosis. J Mol Histol. 2021 Feb;52(1):125-134. doi: 10.1007/s10735-020-09929-x. Epub 2020 Nov 27. PMID: 33245472. 16: Ogunlade B, Fidelis OP, Afolayan OO, Agie JA. Neurotherapeutic and antioxidant response of D-ribose-L-Cysteine nutritional dietary supplements on Alzheimer-type hippocampal neurodegeneration induced by cuprizone in adult male wistar rat model. Food Chem Toxicol. 2021 Jan;147:111862. doi: 10.1016/j.fct.2020.111862. Epub 2020 Nov 18. PMID: 33217524. 17: Klein B, Mrowetz H, Kreutzer C, Rotheneichner P, Zaunmair P, Lange S, Coras R, Couillard-Despres S, Rivera FJ, Aigner L. DCX+ neuronal progenitors contribute to new oligodendrocytes during remyelination in the hippocampus. Sci Rep. 2020 Nov 18;10(1):20095. doi: 10.1038/s41598-020-77115-w. PMID: 33208869; PMCID: PMC7674453. 18: Titus HE, Chen Y, Podojil JR, Robinson AP, Balabanov R, Popko B, Miller SD. Pre-clinical and Clinical Implications of "Inside-Out" vs. "Outside-In" Paradigms in Multiple Sclerosis Etiopathogenesis. Front Cell Neurosci. 2020 Oct 27;14:599717. doi: 10.3389/fncel.2020.599717. PMID: 33192332; PMCID: PMC7654287. 19: Gholami S, Mirian M, Eftekhari SM, Aliomrani M. Apamin administration impact on miR-219 and miR-155-3p expression in cuprizone induced multiple sclerosis model. Mol Biol Rep. 2020 Nov;47(11):9013-9019. doi: 10.1007/s11033-020-05959-6. Epub 2020 Nov 10. PMID: 33174081. 20: Thompson KK, Tsirka SE. Guanabenz modulates microglia and macrophages during demyelination. Sci Rep. 2020 Nov 9;10(1):19333. doi: 10.1038/s41598-020-76383-w. PMID: 33168944; PMCID: PMC7653931.

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