D9628

Sigma-Aldrich

3,4-Dihydroxy-L-phenylalanine

≥98% (TLC)

Synonym(s):
L-DOPA, L-3-Hydroxytyrosine, Levodopa, 3-(3,4-Dihydroxyphenyl)-L-alanine
Linear Formula:
(HO)2C6H3CH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
197.19
Beilstein/REAXYS Number:
2215169
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥98% (TLC)

form

powder

application(s)

peptide synthesis: suitable

color

white to off-white

mp

276-278 °C (lit.)

storage temp.

room temp

SMILES string

N[C@@H](Cc1ccc(O)c(O)c1)C(O)=O

InChI

1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1

InChI key

WTDRDQBEARUVNC-LURJTMIESA-N

Gene Information

human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)
mouse ... DRD1(13488), DRD2(13489), DRD3(13490), DRD4(13491), DRD5(13492)
rat ... DRD1(24316), DRD2(24318), DRD3(29238), DRD4(25432), DRD5(25195)

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Application

3,4-Dihydroxy-L-phenylalanine or L-DOPA has been used to stain melanocytes. It has also been used to study its effects on a Drosophila model of Parkinson′s disease.

Packaging

5, 25, 100, 500 g in poly bottle

Biochem/physiol Actions

3,4-Dihydroxy-L-phenylalanine or L-DOPA is a natural isomer of the immediate precursor of dopamine that crosses the blood-brain barrier. It is used for the treatment of Parkinson′s disease and is a product of tyrosine hydroxylase.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Effects of small-molecule amyloid modulators on a Drosophila model of Parkinson?s disease
Malgorzata Pokrzywa
PLoS ONE (2017)
Primary culture of human face skin melanocytes for the study of hyperpigmentation
Cytotechnology, 66(6) (2014)
Alan J. Sinclair, John E. Morley, Bruno Vellas
Pathy's Principles and Practice of Geriatric Medicine (2012)
Sebastiaan P van Kessel et al.
Nature communications, 10(1), 310-310 (2019-01-20)
Human gut microbiota senses its environment and responds by releasing metabolites, some of which are key regulators of human health and disease. In this study, we characterize gut-associated bacteria in their ability to decarboxylate levodopa to dopamine via tyrosine decarboxylases....
Vincent J J Odekerken et al.
Neurology, 84(13), 1355-1361 (2015-03-01)
To assess the neuropsychological outcome 12 months after bilateral deep brain stimulation (DBS) of the globus pallidus pars interna (GPi) or subthalamic nucleus (STN) for advanced Parkinson disease. We randomly assigned patients to receive either GPi DBS or STN DBS....

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