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D009

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
EC Number:
200-445-2
UNSPSC Code:
12352200
MDL number:
MFCD00002598
Beilstein/REAXYS Number:
2215169
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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

Biochem/physiol Actions

Precursor to dopamine; antiparkinsonian agent

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GHS07

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Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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
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