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H4381

Sigma-Aldrich

6-Hydroxydopamine hydrochloride

≥97% (titration), powder

Synonym(s):
2,4,5-Trihydroxyphenethylamine hydrochloride, 2,5-Dihydroxytyramine hydrochloride, 2-(2,4,5-Trihydroxyphenyl)ethylamine hydrochloride, 6-OHDA
Linear Formula:
(HO)3C6H2CH2CH2NH2 · HCl
CAS Number:
Molecular Weight:
205.64
Beilstein:
4274007
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Packaging

100, 500 mg in glass insert
1 g in glass bottle

Biochem/physiol Actions

Neurotoxin that destroys catecholaminergic terminals.

Caution

Hygroscopic

Reconstitution

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

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Certificate of Analysis

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Certificate of Origin

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