154318
3,4-Dihydroxy-L-phenylalanine
optical purity ee: 99% (GLC), 99%
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:
Molecular Weight:
197.19
EC Number:
200-445-2
UNSPSC Code:
12352103
MDL number:
Beilstein/REAXYS Number:
2215169
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
SMILES string
N[C@@H](Cc1ccc(O)c(O)c1)C(O)=O
assay
99%
optical activity
[α]25/D −11°, c = 1 in 1 M HCl
optical purity
ee: 99% (GLC)
mp
276-278 °C (lit.)
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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
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
Damian M Herz et al.
Annals of neurology, 75(6), 829-836 (2014-06-04)
In Parkinson disease (PD), long-term treatment with the dopamine precursor levodopa gradually induces involuntary "dyskinesia" movements. The neural mechanisms underlying the emergence of levodopa-induced dyskinesias in vivo are still poorly understood. Here, we applied functional magnetic resonance imaging (fMRI) to
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
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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