H4381

6-Hydroxydopamine hydrochloride

Name: 6-Hydroxydopamine hydrochloride
Brand: SIGMA

≥97% (titration), powder, neurotoxin

Sinónimos:

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

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About This Item

Fórmula lineal:

(HO)₃C₆H₂CH₂CH₂NH₂· HCl

Número CAS:

28094-15-7

Peso molecular:

205.64

NACRES:

NA.77

PubChem Substance ID:

24895641

UNSPSC Code:

12352116

EC Number:

248-837-2

MDL number:

MFCD00012895

Beilstein/REAXYS Number:

4274007

Nombre del producto

6-Hydroxydopamine hydrochloride, ≥97% (titration), powder

InChI key

QLMRJHFAGVFUAC-UHFFFAOYSA-N

InChI

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

SMILES string

Cl.NCCc1cc(O)c(O)cc1O

assay

≥97% (titration)

form

powder

color

off-white to brown

mp

232-233 °C (dec.) (lit.)

solubility

H₂O: >50 mg/mL, clear, yellow to brown

storage temp.

room temp

Quality Level

100

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Categorías relacionadas

Bioactive Small Molecules

Application

6-hydroxydopamine hydrochloride has been used:

to induce Parkinson′s disease (PD) in rats
to analyse cytotoxic effect of 6-OHDA on PC12 cell line
to induce noradrenergic (NA) neuron deletion from the locus-coeruleus

Biochem/physiol Actions

Neurotoxin that destroys catecholaminergic terminals.

Disclaimer

Hygroscopic

General description

6-Hydroxydopamine hydrochloride (6-OHDA) is a neurotoxin, commonly used to induce Parkinson′s disease (PD). 6-OHDA causes death of dopaminergic neurons in substantia nigra pars compacta progressively mimicking PD. 6-OHDA is highly oxidizable and cannot cross blood brain barrier. 6-OHDA exerts cytotoxicity by generating reactive oxygen species, initiating cellular stress and cell death. 6-OHDA leads to neuronal cell death in many in vitro models like primary neuronal culture, human neuroblastoma cell line and rat adrenal pheochromocytoma cell line, PC12.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Preparation Note

Dissolve in oxygen-free water containing 0.1% sodium metabisulfite or other antioxidants.

Solutions should be freshly prepared and protected from exposure to light. Solutions turn red as it oxidizes.

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Molecular mechanisms of 6-hydroxydopamine-induced cytotoxicity in PC12 cells: involvement of hydrogen peroxide-dependent and-independent action

Saito Y, et al.

Free Radical Biology & Medicine, 42(5), 675-685 (2007)

The 6-hydroxydopamine model and parkinsonian pathophysiology: Novel findings in an older model

Hernandez-Baltazar D, et al.

Neurologia (Barcelona, Spain), 32(8), 533-539 (2017)

Human induced pluripotent stem cell-derived neurons improve motor asymmetry in a 6-hydroxydopamine-induced rat model of Parkinson's disease

Han F, et al.

Cytotherapy, 17(5), 665-679 (2015)

MiR-410 exerts neuroprotective effects in a cellular model of Parkinson's disease induced by 6-hydroxydopamine via inhibiting the PTEN/AKT/mTOR signaling pathway.

Hanming Ge et al.

Experimental and molecular pathology, 109, 16-24 (2019-05-09)

Parkinson's disease (PD) is a chronic neurodegenerative disease characterized by loss of dopaminergic neurons in the substantia nigra. Recently, microRNAs (miRNAs) were emerging as important mediators in dopaminergic neuron biology. This study determined miR-410 expression in the 6-hydroxydopamine (6-OHDA)-induced in

Parkin promotes proteasomal degradation of p62: implication of selective vulnerability of neuronal cells in the pathogenesis of Parkinson's disease.

Pingping Song et al.

Protein & cell, 7(2), 114-129 (2016-01-10)

Mutations or inactivation of parkin, an E3 ubiquitin ligase, are associated with familial form or sporadic Parkinson's disease (PD), respectively, which manifested with the selective vulnerability of neuronal cells in substantia nigra (SN) and striatum (STR) regions. However, the underlying

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