oxalic bis(cyclohexylidenehydrazide)

Names

[ CAS No. ]:
370-81-0

[ Name ]:
oxalic bis(cyclohexylidenehydrazide)

[Synonym ]:
Dicyclohexanoneoxaly dihydrazone
MFCD00001659
Bis(cyclohexanone) Oxalyldihydrazone
oxalic bis(cyclohexylidenehydrazide)
N,N'-bis(cyclohexylideneamino)oxamide
Oxalic acid bis(cyclohexylidenehydrazide)
Ethanedioic acid, bis(2-cyclohexylidenehydrazide)
Cuprizon,Cuprizone,Oxalic acid bis(cyclohexylidenehydrazide)
N',N'-Dicyclohexylideneethanedihydrazide
Bis(cyclohexanone)oxalyldihydrazone
Cupferazone
Oxalic Acid Bis-(Cyclohexylidenehydrazide)
EINECS 206-729-2

Biological Activity

[Description]:

Cuprizone is a chelator used as a reagent for copper analysis. Cuprizone is frequently used for studying factors that affect oligodendrocytes death and myelin loss[1][2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[In Vivo]

Cuprizone (0.5 mg/100 mg of diet and water given ad lib; p.o.) produces severe status spongious in the CNS, most prominently in the brain stem and cerebellar white matter of mice[1].

[References]

[1]. Suzuki K, et al. Status spongiosus of CNS and hepatic changes induced by cuprizone (biscyclohexanone oxalyldihydrazone). Am J Pathol. 1969 Feb;54(2):307-25.

[2]. Sanadgol N, et al. Alpha-lipoic acid mitigates toxic-induced demyelination in the corpus callosum by lessening of oxidative stress and stimulation of polydendrocytes proliferation. Metab Brain Dis. 2018 Feb;33(1):27-37.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Melting Point ]:
210-214 °C(lit.)

[ Molecular Formula ]:
C₁₄H₂₂N₄O₂

[ Molecular Weight ]:
278.350

[ Exact Mass ]:
278.174286

[ PSA ]:
82.92000

[ LogP ]:
0.85

[ Index of Refraction ]:
1.626

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RO2520000

CHEMICAL NAME :: Oxalic acid, bis(cyclohexylidenehydrazide)

CAS REGISTRY NUMBER :: 370-81-0

BEILSTEIN REFERENCE NO. :: 2388004

LAST UPDATED :: 199701

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C14-H22-N4-O2

MOLECULAR WEIGHT :: 278.40

WISWESSER LINE NOTATION :: L6YTJ AUNMVVMNU- AL6YTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 29400 mg/kg/7W-C

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 20160 mg/kg/8W-C

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - monoamine oxidase

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 24 gm/kg

SEX/DURATION :: female 3-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - live birth index (measured after birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 40 gm/kg

SEX/DURATION :: female 3-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - stillbirth

MUTATION DATA

TEST SYSTEM :: Rodent - rat

DOSE/DURATION :: 14 gm/kg/14D (Continuous)

REFERENCE :: EJBCAI European Journal of Biochemistry. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1967- Volume(issue)/page/year: 47,313,1974

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R21/22

[ Safety Phrases ]:
S24/25-S2

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
RO2520000

[ Packaging Group ]:
I; II; III

[ Hazard Class ]:
6.1

[ HS Code ]:
29280090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2928000090

[ Summary ]:
2928000090 other organic derivatives of hydrazine or of hydroxylamine VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

Articles

Effect of high-dose 1.25 dihydroxyvitamin D3 on remyelination in the cuprizone model.

APMIS 122(12) , 1178-86, (2014)

Vitamin D supplementation is increasingly recommended to patients with multiple sclerosis (MS). To study the effect of high-dose vitamin D on remyelination, female C57Bl/6 mice were demyelinated with ...

Behavioural changes observed in demyelination model shares similarities with white matter abnormalities in humans.

Behav. Brain Res. 287 , 265-75, (2015)

Multiple sclerosis (MS) is a chronic, inflammatory, demyelinating disease of the central nervous system (CNS). Further to the symptoms resulting from demyelination, new studies point to the involvemen...

Prion protein and copper cooperatively protect neurons by modulating NMDA receptor through S-nitrosylation.

Antioxid. Redox Signal. 22(9) , 772-84, (2015)

Several neurodegenerative disorders show alterations in glutamatergic synapses and increased susceptibility to excitotoxicity. Mounting evidence suggests a central role for the cellular prion protein ...

Related Compounds

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