L-3,4-DIHYDROXYPHENYLALANINE METHYL ESTER HYDROCHLORIDE

CAS No.：1421-65-4

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L-3,4-DIHYDROXYPHENYLALANINE METHYL ESTER HYDROCHLORIDE Basic information

Product Name:	L-3,4-DIHYDROXYPHENYLALANINE METHYL ESTER HYDROCHLORIDE
Synonyms:	L-3,4-DIHYDROXYPHENYLALANINE METHYLESTER HYDROCHLO;methyldopa hydrochloride;2-Amino-3-(3,4-dihydroxyphenyl)-propanoic acid methylester hydrochloride;Dopamine, methyl ester;L-Tyrosine, 3-hydroxy-, methyl ester, hydrochloride;Nsc295453;L-DOPA Methyl Ester Hydrochloride;3,4-Dihydroxyphenyl-L-alanine methyl ester hydrochloride
CAS:	1421-65-4
MF:	C10H14ClNO4
MW:	247.68
EINECS:
Product Categories:	Dopamine receptor;Amino Acids & Derivatives;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:	1421-65-4.mol

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

Melting point	174-175℃
storage temp.	-20°C
solubility	DMSO (Slightly), Methanol (Slightly)
form	solid
color	white

Safety Information

WGK Germany

MSDS Information

Provider	Language
SigmaAldrich	English

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].
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).

L-3,4-DIHYDROXYPHENYLALANINE METHYL ESTER HYDROCHLORIDE Preparation Products And Raw materials

Raw materials	Diethyl ether-->Methanol-->Acetyl chloride-->Levodopa
Preparation Products	(S)-Methyl 2-((tert-butoxycarbonyl)aMino)-3-(3,4-dihydroxyphenyl)propanoate

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