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162957

Sigma-Aldrich

6-Hydroxydopamine hydrobromide

95%

Synonym(s):

2,4,5-Trihydroxyphenethylamine hydrobromide, 2,5-Dihydroxytyramine hydrobromide, 2-(2,4,5-Trihydroxyphenyl)ethylamine hydrobromide, 6-OHDA

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About This Item

Linear Formula:
(HO)3C6H2CH2CH2NH2 · HBr
CAS Number:
636-00-0
Molecular Weight:
250.09
Beilstein:
3713280
EC Number:
211-247-0
MDL number:
MFCD00012894
UNSPSC Code:
12352116
PubChem Substance ID:
329751177
NACRES:
NA.77

Quality Level

100

Assay

95%

form

powder

mp

216-220 °C (lit.)

storage temp.

−20°C

SMILES string

Br.NCCc1cc(O)c(O)cc1O

InChI

1S/C8H11NO3.BrH/c9-2-1-5-3-7(11)8(12)4-6(5)10;/h3-4,10-12H,1-2,9H2;1H

InChI key

MLACDGUOKDOLGC-UHFFFAOYSA-N

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General description

Solutions should be freshly prepared and protected from exposure to light.

Application

6-Hydroxydopamine hydrobromide has been used:
  • to induce Parkinson′s disease (PD) in mouse models to study the effects of tubastatin A (TBA) on nucleotide-binding oligomerization domain and leucine-rich repeat pyrin 3 domain (NLRP3) activation and cell injury in SH-SY5Y cells
  • to induce pharmacological ablation of the sympathetic nerves to study the effect of hepatic sympathetic nerve activity (SNA) on hepatic steatosis during diet-induced obesity in mice
  • to induce oxidative stress in mesencephalic cells to study its effect on p75NTR signaling in neuronal cells of the ventral mesencephalon

Biochem/physiol Actions

6-Hydroxydopamine hydrobromide (6-OHDA) is a neurotoxin that elicits oxidative damage and destroys catecholaminergic or sympathetic terminals. It is commonly used to induce Parkinson′s disease in the experimental model. 6-OHDA exerts cytotoxicity by generating reactive oxygen species, initiating cellular stress and cell death.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Woori Kim et al.
Neurobiology of aging, 35(7), 1712-1721 (2014-02-25)
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Toxicology, 304, 109-119 (2013-01-01)
6-Hydroxydopamine (6-OHDA) is a neurotoxin that generates an experimental model of Parkinson's disease in rodents and is commonly employed to induce a lesion in dopaminergic pathways. The characterization of those molecular mechanisms linked to 6-OHDA-induced early toxicity is needed to
C C Real et al.
Neuroscience, 237, 118-129 (2013-02-12)
Physical exercise is known to produce beneficial effects to the nervous system. In most cases, brain-derived neurotrophic factor (BDNF) is involved in such effects. However, little is known on the role of BDNF in exercise-related effects on Parkinson's disease (PD).
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Experimental neurology, 248, 213-223 (2013-06-19)
The pedunculopontine nucleus (PPN) controls various physiological functions, whilst being deemed a suitable target for low-frequency stimulation therapy for alleviating aspects of Parkinson's disease (PD). Previous studies showed that the PPN contains mainly cholinergic, γ-aminobutyric acid (GABA)ergic and glutamatergic neurons.
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