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Merck
CN

D009

Sigma-Aldrich

3,4-Dihydroxy-L-phenylalanine

solid

Synonym(s):

3-(3,4-Dihydroxyphenyl)-L-alanine, L-3-Hydroxytyrosine, L-DOPA, Levodopa

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About This Item

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:
12352200

Key Documents

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form

solid

optical activity

[α]20/D −11.5°, c = 1 in 1 M HCl(lit.)

color

white

mp

276-278 °C (lit.)

solubility

H2O: 1.6 mg/mL
aqueous acid: soluble
aqueous base: unstable
ethanol: slightly soluble

storage temp.

2-8°C

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

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Biochem/physiol Actions

Precursor to dopamine; antiparkinsonian agent

Disclaimer

Light Sensitive

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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:
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
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
Ezekiel J Maier et al.
Genome research, 25(5), 690-700 (2015-02-04)
Key steps in understanding a biological process include identifying genes that are involved and determining how they are regulated. We developed a novel method for identifying transcription factors (TFs) involved in a specific process and used it to map regulation
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