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D1507

Sigma-Aldrich

L-3,4-Dihydroxyphenylalanine methyl ester hydrochloride

≥98% (HPLC), solid,  L-DOPA precursor

Synonym(s):

Methyl L-DOPA hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C10H13NO4 · HCl
CAS Number:
1421-65-4
Molecular Weight:
247.68
MDL number:
MFCD00038958
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24278358
NACRES:
NA.77

product name

L-3,4-Dihydroxyphenylalanine methyl ester hydrochloride, solid

form

solid

Quality Level

200

color

white to off-white

storage temp.

−20°C

SMILES string

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

InChI

1S/C10H13NO4.ClH/c1-15-10(14)7(11)4-6-2-3-8(12)9(13)5-6;/h2-3,5,7,12-13H,4,11H2,1H3;1H/t7-;/m0./s1

InChI key

WFGNJLMSYIJWII-FJXQXJEOSA-N

Application

L-3,4-Dihydroxyphenylalanine methyl ester hydrochloride has been used:
  • in treating 6-hydroxydopamine induced lesions mice serotonin neurons
  • in tyrosinase activity in B16F10 skin melanoma cells
  • to test its neuroprotective effect in mesencephalic neurons

Biochem/physiol Actions

L-3,4-Dihydroxyphenylalanine methyl ester is a precursor to L-DOPA that crosses the blood-brain barrier. Antiparkinsonian agent L-DOPA methyl ester elicits antitumor functionality in leukemia and melanoma.

Caution

Light sensitive

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Xinxin Yang et al.
International journal of nanomedicine, 7, 2077-2086 (2012-05-24)
Levodopa remains the most effective drug in the treatment of Parkinson's disease. However, long-term administration of levodopa induces motor complications, such as levodopa-induced dyskinesia. The mechanisms underlying levodopa-induced dyskinesia are not fully understood. In this study, we prepared levodopa methyl
L-Dopa methyl ester as a new antitumour agent
Wick MM
Nature, 269(5628), 512-513 (1977)
Muriel Geurts et al.
Neuroscience letters, 333(2), 146-150 (2002-11-07)
The role of dopaminergic transmission on striatal mRNA levels of regulators of G protein signalling proteins RGS 2-12 was evaluated by quantitative in situ hybridisation. A single injection of L-dopa (50 mg/kg i.p.) significantly increased the RGS2 mRNA level (by
Kevin W McCairn et al.
Journal of neurophysiology, 101(4), 1941-1960 (2009-01-24)
Competing theories seek to account for the therapeutic effects of high-frequency deep brain stimulation (DBS) of the internal globus pallidus (GPi) for medically intractable Parkinson's disease. To investigate this question, we studied the spontaneous activity of 102 pallidal neurons during
3-O-Methyldopa inhibits astrocyte-mediated dopaminergic neuroprotective effects of l-DOPA
Asanuma M and Miyazaki I
BMC Neuroscience, 17(1), 52-52 (2016)
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