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Merck
CN

H4381

6-Hydroxydopamine hydrochloride

≥97% (titration), powder, neurotoxin

Synonym(s):

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

Linear Formula:
(HO)3C6H2CH2CH2NH2 · HCl
CAS Number:
28094-15-7
Molecular Weight:
205.64
Beilstein:
4274007
EC Number:
248-837-2
MDL number:
MFCD00012895
UNSPSC Code:
12352116
PubChem Substance ID:
24895641
NACRES:
NA.77

Key Documents

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Product Name

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

Quality Level

100

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

SMILES string

Cl.NCCc1cc(O)c(O)cc1O

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

InChI key

QLMRJHFAGVFUAC-UHFFFAOYSA-N

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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.

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.

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.

Other Notes

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

Disclaimer

Hygroscopic

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW7704
MKCV6213
MKCQ5002
MKCN8919
MKCL2977

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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)
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
Kryspin Andrzejewski et al.
Journal of biomedical science, 24(1), 24-24 (2017-03-30)
Malfunctioning of the serotonergic system in Parkinson's disease may contribute to non-motor symptoms such as respiratory complications. Thus the aim of our study was to investigate the role of serotonin 5-HT Wistar rats were lesioned unilaterally with double 6-hydroxydopamine (6-OHDA)
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