1421-65-4

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 NO: 1421-65-4
• Molecular Formula: C₁₀H₁₃NO₄*ClH
• Molecular Weight: 247.68
• Product Categories: Dopamine receptor;Amino Acids & Derivatives;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1421-65-4.mol

Chemical Properties

• Melting Point: 174-175℃
• Boiling Point: 384.4 °C at 760 mmHg
• Flash Point: 186.3 °C
• Appearance: white/solid
• Density: 1.322 g/cm³
• Vapor Pressure: 1.86E-06mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: L-3,4-DIHYDROXYPHENYLALANINE METHYL ESTER HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: L-3,4-DIHYDROXYPHENYLALANINE METHYL ESTER HYDROCHLORIDE(1421-65-4)
• EPA Substance Registry System: L-3,4-DIHYDROXYPHENYLALANINE METHYL ESTER HYDROCHLORIDE(1421-65-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1421-65-4(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
L-3,4-dihydroxyphenylalanine methyl ester hydrochloride is used as a precursor to L-DOPA for increasing dopamine concentrations in the brain. It acts as a dopamine D1 receptor agonist and is conventionally used as an antiparkinsonian agent for the treatment of Parkinson's disease and stroke recovery.
2. Used in Neuroprotection:
L-3,4-dihydroxyphenylalanine methyl ester hydrochloride is used as a neuroprotective agent to test its effects in mesencephalic neurons. It has been utilized in treating 6-hydroxydopamine induced lesions in mice serotonin neurons, demonstrating its potential in neuroprotection.
3. Used in Skin Melanoma Cells:
In the field of dermatology, L-3,4-dihydroxyphenylalanine methyl ester hydrochloride is used as a modulator of tyrosinase activity in B16F10 skin melanoma cells. This application highlights its potential role in the treatment and management of skin pigmentation disorders and melanoma.
4. Used as a Dopamine D1 Receptor Agonist:
L-3,4-dihydroxyphenylalanine methyl ester hydrochloride is used as a selective dopamine D1 receptor agonist, which can be beneficial in various neurological and psychiatric conditions where dopamine signaling is impaired or dysregulated.

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).

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

Upstream product

• 67-56-1 methanol 
• 59-92-7 levodopa 
• 60-29-7 diethyl ether 
• 75-36-5 acetyl chloride 

Downstream Products

• 185063-07-4 nitroveratryloxycarbonyl-L-dopa methyl ester 
• 1418029-45-4 methyl 3-(3,4-dihydroxyphenyl)-(2S)-2-((2E)-3-(4-hydroxyphenyl)acrylamido)propanoate 

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