Dopamine, methyl ester

Base Information

• Chemical Name: Dopamine, methyl ester
• CAS No.: 1421-65-4
• Molecular Formula: C10H14ClNO4
• Molecular Weight: 247.678
• Hs Code.: 2923900090
• NSC Number: 295453,166838
• DSSTox Substance ID: DTXSID30859644
• ChEMBL ID: CHEMBL1439696
• Mol file: 1421-65-4.mol

Synonyms:40611-00-5;SMR000145236;MLS000551310;NSC-295453;Dopamine, methyl ester;SCHEMBL1149493;CHEMBL1439696;methyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate hydrochloride;DTXSID30859644;NSC166838;NSC295453;AKOS030511204;NSC-166838;FT-0633533;DL-3-Hydroxytyrosine methyl ester hydrochloride;EN300-717696;MLS-0073729.0001;3,4-Dihydroxy-DL-phenylalanine methyl ester HCl;METHYL 2-AMINO-3-(3,4-DIHYDROXYPHENYL)PROPANOATE HYDROCHLORIDE

Chemical Property of Dopamine, methyl ester

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 1.86E-06mmHg at 25°C
• Melting Point: 174-175℃
• Boiling Point: 384.4 °C at 760 mmHg
• Flash Point: 186.3 °C
• PSA: 92.78000
• Density: 1.322 g/cm³
• LogP: 1.64290
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 247.0611356
• Heavy Atom Count: 16
• Complexity: 222

Purity/Quality:

98%,99%, ^*data from raw suppliers

L-DOPA Methyl Ester Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC(=C(C=C1)O)O)N.Cl
• 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.
• Uses: Precursor to L-DOPA that crosses the blood-brain barrier; antiparkinsonian agent. L-3,4-Dihydroxyphenylalanine methyl ester hydrochloride has been used:in treating 6-hydroxydopamine induced lesions mice serotonin neuronsin tyrosinase activity in B16F10 skin melanoma cellsto test its neuroprotective effect in mesencephalic neurons Selective Dopamine D1 receptor agonist.

Technology Process of Dopamine, methyl ester

There total 5 articles about Dopamine, methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methanol (67-56-1) + levodopa (59-92-7,90638-38-3) → L-dopa methyl ester hydrochloride (1421-65-4)

Guidance literature:

With thionyl chloride; at 20 ℃; for 18h;

DOI:10.1021/jm010178b

Reference yield: 94.0%

levodopa (59-92-7,90638-38-3) + acetyl chloride (75-36-5) → L-dopa methyl ester hydrochloride (1421-65-4)

Guidance literature:

In methanol; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.molpharmaceut.7b00569

Reference yield:

diethyl ether (60-29-7,927820-24-4) + levodopa (59-92-7,90638-38-3) → L-dopa methyl ester hydrochloride (1421-65-4)

Guidance literature:

In methanol, thionyl chloride;

upstream raw materials:

methanol

levodopa

diethyl ether

acetyl chloride

Downstream raw materials:

methyl (S)-2-amino-3-<3,4-bis(tert-butyldimethylsilyloxy)phenyl>propanoate

3-(3,4-dihydroxy-phenyl)-2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]propionic acid

methyl N-(tert-butyloxycarbonyl)-3,4-bis(hydroxy)phenylalanine carboxylate

(S)-methyl 2-(benzyloxycarbonylamino)-3-(3,4-dihydroxyphenyl)propanoate

Refernces

• 1、 Liu, Shih-I,Haung, Jia-Yun,Barve, Indrajeet J.,Huang, Sheng-Cih,Sun, Chung-Ming. "Enantioselective Synthesis of Hydantoin and Diketopiperazine-Fused Tetrahydroisoquinolines via Pictet-Spengler Reaction". . p. 336 - 344. Retrieved 2019.
• 2、 -. "PROCESS FOR PREPARING PURIFIED LEVODOPAMIDE FREE BASE". Paragraph 126; 127. . Retrieved 2020/03/05.
• 3、 -. "L-DOPA AND/OR DOPA DECARBOXYLSE INHIBITORS CONJUGATED TO SUGAR FOR THE TREATMENT OF DOPAMINE-RESPONSIVE DISORDERS". Paragraph 00221; 00222; 00223. . Retrieved 2020/07/05.