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V900425

Sigma-Aldrich

3,4-Dihydroxy-L-phenylalanine

Vetec™, reagent grade, 98%

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Synonym(s):
3-(3,4-Dihydroxyphenyl)-L-alanine, L-3-Hydroxytyrosine, L-DOPA, Levodopa
Linear Formula:
(HO)2C6H3CH2CH(NH2)CO2H
CAS Number:
59-92-7
Molecular Weight:
197.19
Beilstein:
2215169
EC Number:
200-445-2
MDL number:
MFCD00002598
UNSPSC Code:
12352209
PubChem Substance ID:
329829833

grade

reagent grade

product line

Vetec™

Assay

98%

mp

276-278 °C (lit.)

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 ... DRD3(1814)

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Legal Information

Vetec is a trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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A P de Jong et al.
Clinica chimica acta; international journal of clinical chemistry, 171(1), 49-61 (1988-01-15)
L-3-(3,4-Dihydroxyphenyl)alanine (DOPA) and its 3-O-methyl metabolite (OMD) were measured in plasma and cerebrospinal fluid by a new assay which combines N,O-acetylation of amino acids in aqueous media, preparation of pentafluorobenzyl esters under anhydrous conditions, and analysis by gas chromatography-electron capture
Roshan Cools
Neuroscience and biobehavioral reviews, 30(1), 1-23 (2005-06-07)
It is well recognised that patients with Parkinson's disease exhibit cognitive deficits, even in the earliest disease stages. Whereas, L-DOPA therapy in early Parkinson's disease is accepted to improve the motor symptoms, the effects on cognitive performance are more complex:
Nicolas Morin et al.
Experimental neurology, 256, 105-116 (2013-01-31)
The treatment of motor symptoms of Parkinson disease (PD) with the dopamine (DA) precursor, l-3,4-dihydroxyphenylalanine (l-DOPA) introduced 50years ago still remains a very effective medication. However, involuntary movements termed l-DOPA-induced dyskinesias (LID) appear in the vast majority of PD patients
Molly J Crockett et al.
Current biology : CB, 25(14), 1852-1859 (2015-07-07)
An aversion to harming others is a core component of human morality and is disturbed in antisocial behavior. Deficient harm aversion may underlie instrumental and reactive aggression, which both feature in psychopathy. Past work has highlighted monoaminergic influences on aggression
Gagandeep Jain et al.
The New phytologist, 207(4), 1075-1083 (2015-04-15)
The capacity to synthesize betalains has arisen in diverse phylogenetic lineages across the Caryophyllales, and because betalainic plants often grow in deserts, sand dunes, or salt marshes, it is likely that these pigments confer adaptive advantages. However, possible functional roles
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