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162957

Sigma-Aldrich

6-Hydroxydopamine hydrobromide

95% (HPLC), powder, neurotoxin 

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

product name

6-Hydroxydopamine hydrobromide, 95%

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)
Dopamine (DA) neurons in sporadic Parkinson's disease (PD) display dysregulated gene expression networks and signaling pathways that are implicated in PD pathogenesis. Micro (mi)RNAs are regulators of gene expression, which could be involved in neurodegenerative diseases. We determined the miRNA
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Immunity, 53(2), 417-428 (2020-08-01)
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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).
Bing Zhang et al.
Nature, 577(7792), 676-681 (2020-01-24)
Empirical and anecdotal evidence has associated stress with accelerated hair greying (formation of unpigmented hairs)1,2, but so far there has been little scientific validation of this link. Here we report that, in mice, acute stress leads to hair greying through
Fernando Eduardo Padovan-Neto et al.
Neuroscience letters, 541, 126-131 (2013-02-23)
Rodents with lesion of dopaminergic pathway when receiving repeated l-3,4-dihydroxiphenylalanine (l-DOPA) treatment develop abnormal involuntary movements called dyskinesia. We demonstrated that nitric oxide synthase (NOS) inhibitors mitigate l-DOPA-induced dyskinesia in rodents. The aim of the present study was to verify
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