6-HYDROXYDOPAMINE HYDROBROMIDE

Names

[ CAS No. ]:
636-00-0

[ Name ]:
6-HYDROXYDOPAMINE HYDROBROMIDE

[Synonym ]:
5-(2-Aminoethyl)-1,2,4-benzenetriol hydrobromide (1:1)
1,2,4-Benzenetriol, 5-(2-aminoethyl)-, hydrobromide (1:1)
5-(2-aminoethyl)benzene-1,2,4-triol,hydrobromide
5-(2-Aminoethyl)benzene-1,2,4-triol hydrobromide (1:1)
EINECS 211-247-0
MFCD00012894
Oxidopamine (hydrobromide)

Biological Activity

[Description]:

Oxidopamine hydrobromide is a selective catecholaminergic neurotoxin, depletes brain catecholamine levels via uptake and accumulation by a transport mechanism specific to these neurons. In vitro: Oxidopamine hydrobromide-induced apoptosis of PC12 cells was initiated by superoxide generation followed by caspase cascade activation, which was associated with the suppressed Akt phosphorylation and increased p38 phosphorylation. It is likely that pCPT-cAMP prevented the Oxidopamine hydrobromide-induced apoptosis via activation of the PI3-kinase/Akt pathway without any effect on superoxide generation or mitochondrial membrane depolarization. [1]In vivo the presence of sulfhydryl antioxidants protected against neuronal degeneration in the striatum, which was particularly remarkable in the case of CySH and was attributed to its capacity to remove the H2O2 produced in the autoxidation of Oxidopamine hydrobromide.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor

Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor

Signaling Pathways >> Autophagy >> Mitophagy

Research Areas >> Cancer

[References]

[1]. Fujita H et al. Cell-permeable cAMP analog suppresses 6-hydroxydopamine-induced apoptosis in PC12 cells through the activation of the Akt pathway. Brain Res. 2006 Oct 3;1113(1):10-23.

[2]. Soto-Otero R et al. Autoxidation and neurotoxicity of 6-hydroxydopamine in the presence of some antioxidants: potential implication in relation to the pathogenesis of Parkinson's disease. J Neurochem. 2000 Apr;74(4):1605-12.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
406ºC at 760 mmHg

[ Melting Point ]:
216-220 °C(lit.)

[ Molecular Formula ]:
C₈H₁₂BrNO₃

[ Molecular Weight ]:
250.090

[ Flash Point ]:
199.3ºC

[ Exact Mass ]:
249.000046

[ PSA ]:
86.71000

[ LogP ]:
1.96300

[ Appearance of Characters ]:
solid | tan to brown

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DC4600000

CHEMICAL NAME :: 1,2,4-Benzenetriol, 5-(2-aminoethyl)-, hydrobromide

CAS REGISTRY NUMBER :: 636-00-0

LAST UPDATED :: 198910

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C8-H11-N-O3.Br-H

MOLECULAR WEIGHT :: 250.12

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 100 mg/kg

SEX/DURATION :: female 21-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Paternal Effects - other effects on male Reproductive - Maternal Effects - parturition

REFERENCE :: JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 76,415,1986

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DC4600000

[ HS Code ]:
2922299090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922299090

[ Summary ]:
2922299090. other amino-naphthols and other amino-phenols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Rho kinase inhibition by fasudil in the striatal 6-hydroxydopamine lesion mouse model of Parkinson disease.

J. Neuropathol. Exp. Neurol. 73(8) , 770-9, (2014)

Chronic degeneration of nigrostriatal projections, followed by nigral dopaminergic cell death, is a key feature of Parkinson disease (PD). This study examines the neuroprotective potential of the rho ...

Curcumin I mediates neuroprotective effect through attenuation of quinoprotein formation, p-p38 MAPK expression, and caspase-3 activation in 6-hydroxydopamine treated SH-SY5Y cells.

Phytother Res. 28(4) , 611-6, (2014)

6-Hydroxydopamine (6-OHDA) selectively enters dopaminergic neurons and undergoes auto-oxidation resulting in the generation of reactive oxygen species and dopamine quinones, subsequently leading to ap...

Ameliorating effects of curcumin on 6-OHDA-induced dopaminergic denervation, glial response, and SOD1 reduction in the striatum of hemiparkinsonian mice.

Eur. Rev. Med. Pharmacol. Sci. 17(10) , 1360-8, (2013)

Inflammation and oxidative stress are believed to contribute to neuronal degeneration of the nigrostriatal dopaminergic (DA) pathway in Parkinson's disease. Curcumin, a component of the yellow curry s...