1421-65-4 Usage
Description
L-3,4-dihydroxyphenylalanine methyl ester hydrochloride, also known as L-DOPA methyl ester, is a neutral derivative of L-DOPA (Levodopa). It is a metabolic precursor of dopamine, which is capable of crossing the blood-brain barrier. L-DOPA methyl ester is formulated for increased solubility compared to the parent compound and is produced from L-tyrosine by tryptamine hydroxylase. In the brain, it is converted to dopamine by the enzyme aromatic L-amino acid decarboxylase. It is a white solid and has various applications in different industries.
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).
Check Digit Verification of cas no
The CAS Registry Mumber 1421-65-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,2 and 1 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1421-65:
(6*1)+(5*4)+(4*2)+(3*1)+(2*6)+(1*5)=54
54 % 10 = 4
So 1421-65-4 is a valid CAS Registry Number.
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
1421-65-4Relevant articles and documents
Boc-Protection on L-DOPA: an Easy Way to Promote Underwater Adhesion
Giuri, Demetra,Jacob, Kiran A.,Ravarino, Paolo,Tomasini, Claudia
, p. 7144 - 7150 (2020)
The ability of mussels to adhere to underwater surfaces has attracted a lot of attention from the scientific community. As proteins containing L-DOPA (3,4-dihydroxyphenyl-l-alanine) are involved in their adhesion, a common strategy to synthesize adhesives
pH stability and antioxidant power of CycloDOPA and its derivatives
Nakagawa, Shiori,Tachrim, Zetryana Puteri,Kurokawa, Natsumi,Ohashi, Fumina,Sakihama, Yasuko,Suzuki, Takeyuki,Hashidoko, Yasuyuki,Hashimoto, Makoto
, (2018)
CycloDOPA (leukodopachrome), a well known metabolite of tyrosine, is a precursor of melanine in mammalian organisms and of the pigment betalain in plants. However, the isolation of cycloDOPA from natural sources has not been widely reported. In the present work, the stabilities of cycloDOPA and cycloDOPA methyl ester at various pH levels were studied. Both compounds were stable under acidic conditions. By contrast, both compounds were unstable when the pH was shifted from neutral to basic to form indole derivatives as major products. Based on the pH stability, cycloDOPA and its derivatives were subjected to the DPPH radical scavenging assay for the first time.
PROCESS FOR PREPARING PURIFIED LEVODOPAMIDE FREE BASE
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Paragraph 126; 127, (2020/03/05)
Disclosed herein, in part, are processes making and purifying L-dopamide free base, such as purified pharmaceutically acceptable L-dopamide free base substantially free of L-dopa. Such processes are useful for providing L-dopamide for the treatment of neu
Substituted pyrrole chromone compound or pharmaceutically acceptable salt thereof and preparation method and application thereof
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Paragraph 0081; 0087-0089, (2019/01/23)
The invention discloses a substituted pyrrole chromone compound or pharmaceutically acceptable salt thereof and a preparation method and application thereof. The structure of the compound or the pharmaceutically acceptable salt thereof is shown in the for
