A toxic dopamine metabolite
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DOPAL

Item No. 18448

Technical Information
Formal Name
3,4-dihydroxy-benzeneacetaldehyde
CAS Number
5707-55-1
Molecular Formula
C8H8O3
Formula Weight
Purity
≥75%
A 10 mg/ml solution in acetonitrile
DMF: 15 mg/mlDMSO: 10 mg/mlEthanol: 15 mg/mlPBS (pH 7.2): 2 mg/ml
SMILES
OC1=C(O)C=CC(CC([H])=O)=C1
InChi Code
InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2
InChi Key
IADQVXRMSNIUEL-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    Product Description

    DOPAL is an aldehyde product of the oxidative deamination of dopamine by monoamine oxidase.1 It can be further oxidized to 3,4-dihydroxyphenylacetic acid (DOPAC) by aldehyde dehydrogenase (ALDH) and, to a lesser extent reduced to 3,4-dihydroxyphenyl ethanol (DOPET; Item No. 70604). DOPAL is toxic to neurons.2,3 It can also oligomerize and precipitate α-synuclein, an event associated with Parkinson’s disease.2 Mice lacking cytosolic and mitochondrial forms of ALDH display increased levels of DOPAL as well as neurodegeneration and motor dysfunction characteristic of Parkinson’s disease.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jinsmaa, Y., Florang, V.R., Rees, J.N., et alProducts of oxidative stress inhibit aldehyde oxidation and reduction pathways in dopamine catabolism yielding elevated levels of a reactive intermediate. Chem. Res. Toxicol. 22(5), 835-841 (2009).

    2. Goldstein, D.S., Sullivan, P., Holmes, C., et alDeterminants of buildup of the toxic dopamine metabolite DOPAL in Parkinson’s disease. J. Neurochem. 126(5), 591-603 (2013).

    3. Panneton, W.M., Kumar, V.B., Gan, Q., et alThe neurotoxicity of DOPAL: Behavioral and stereological evidence for its role in Parkinson disease pathogenesis. PLoS One 5(12), e15251 (2010).

    4. Wey, M.C.Y., Fernandez, E., Martinez, P.A., et alNeurodegeneration and motor dysfunction in mice lacking cytosolic and mitochondrial aldehyde dehydrogenases: implications for Parkinson’s disease. PLoS One 7(2), e31522 (2012).