L-3,4-DIHYDROXYPHENYLALANINE METHYL ESTER HYDROCHLORIDE Chemical Properties

Melting point:

174-175℃

alpha 

+9.0° to +11.0° (20°C, 589nm) (C=2 in methanol)

storage temp. 

-20°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

solid

color 

white

InChI

InChI=1/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-;/s3

InChIKey

WFGNJLMSYIJWII-WMASNCOMNA-N

SMILES

C1(=CC=C(O)C(O)=C1)C[C@H](N)C(=O)OC.Cl |&1:9,r|

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

L-3,4-DIHYDROXYPHENYLALANINE METHYL ESTER HYDROCHLORIDE Usage And Synthesis

Description

L-DOPA (Item No. 13248) is a metabolic precursor of dopamine that is capable of crossing the blood brain barrier to act as a dopamine D₁ receptor agonist. It is produced from L-tyrosine by trysosine hydroxylase. In the brain, L-DOPA is converted to dopamine by the enzyme aromatic L-amino acid decarboxylase. It is conventionally used to increase dopamine concentrations in the brain as a treatment for Parkinson’s disease and stroke recovery. L-DOPA methyl ester is a neutral derivative of L-DOPA formulated for increased solubility compared to the parent compound.

Chemical Properties

White Solid

Uses

Precursor to L-DOPA that crosses the blood-brain barrier; antiparkinsonian agent.

Uses

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

Uses

Selective Dopamine D1 receptor agonist.

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.

in vitro

l-dopa methyl ester is a neutral derivative of l-dopa formulated for increased solubility compared to the parent compound. l-dopa is a metabolic precursor of dopamine that is capable of crossing the blood brain barrier to act as a dopamine d1 receptor agonist [1].

in vivo

on intraperitoneal or subcutaneous administration to mice l-dopa methyl ester was found to be equivalent to l-dopa in reversing reserpine-induced akinesia and producing contraversive circling behaviour in rats. on oral administration the methyl ester was even more active. the administration of l-dopa or the methyl ester had equivalent changes of metabolite levels in striatal and mesolimbic dopamine, homovanillic acid, as well as 3,4-dihydroxyphenylacetic acid [2].

storage

-20°C

References

[1] berends, h. i.,nijlant, j.m.m.,movig, k.l.l., et al. the clinical use of drugs influencing neurotransmitters in the brain to promote motor recovery after stroke; a cochrane systematic review. european journal of physical and rehabilitation medicine 45(4), 621-630 (2009).
[2] cooper dr, marrel c, testa b, van de waterbeemd h, quinn n, jenner p, marsden cd. l-dopa methyl ester--a candidate for chronic systemic delivery of l-dopa in parkinson's disease. clin neuropharmacol. 1984;7(1):89-98.
[3] kleedorfer, b. ,lees, a.j. and stern, g.m. subcutaneous and sublingual levodopa methyl ester in parkinson’s disease. j.neurol.neurosurg.psychiatry 54(4), 373 (1991).

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