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Home > Products >  China Largest Manufacturer factory Supply Levodopa CAS 59-92-7

China Largest Manufacturer factory Supply Levodopa CAS 59-92-7 CAS NO.59-92-7

  • FOB Price: USD: 1.00-2.00 /Kilogram Get Latest Price
  • Min.Order: 1000 Kilogram
  • Payment Terms: L/C,D/A,D/P,T/T,Other
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    AAAAA(50-100)KilogramAAAAA(100-500)Kilogram

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Keywords

  • Levodopa
  • Levodopa
  • 59-92-7

Quick Details

  • ProName: China Largest Manufacturer factory Sup...
  • CasNo: 59-92-7
  • Molecular Formula: 59-92-7
  • Appearance: white powder
  • Application: Pharm chemicals industry
  • DeliveryTime: 3-5 days
  • PackAge: 25KG/Drum
  • Port: Shanghai Guangzhou Qingdao Shenzhen
  • ProductionCapacity: 20 Metric Ton/Month
  • Purity: 99%
  • Storage: 2-8°C
  • Transportation: By air /Sea/ coruier
  • LimitNum: 1000 Kilogram
  • Heavy metal: 10PPM
  • Color: white
  • Melting point: ≥350°C
  • Boiling point: 363.24°C (rough estimate)
  • density: 1.667
  • solubility: 1 M NaOH: 10 mg/mL, dark green
  • Water Solubility: <0.1 g/100 mL at 21 oC
  • Stability: Stable. Combustible. Incompatible with...

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Levodopa Basic information
Product Name: Levodopa
Synonyms: 2-amino-3-(3,4-dihydroxyphenyl)propanoicacid;3,4-Dihydroxyphenylalanine(form2);3,4-Dihydroxyphenyl-L-alanine;3,4-DIHYDROXY-L-PHENYLALANINE;3,4-L-DIHYDROXYPHENYLALANINE;3-(3,4-DIHYDROXYPHENYL)-L-ALANINE;3-HYDROXY-L-TYROSINE;BETA-(3,4-DIHYDROXYPHENYL)-L-ALANINE
CAS: 59-92-7
MF: C9H11NO4
MW: 197.19
EINECS: 200-445-2
Product Categories: Inhibitors;plant extract;Amino Acids;Biochemistry;Biological-modified Amino Acids;Dopamine receptor;Pharmaceutical;Nutritional Supplements;Natural Plant Extract;Amino Acids & Derivatives;Chiral Reagents;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals;Plant extracts;Herb extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;LARADOPA
Mol File: 59-92-7.mol
Levodopa Structure
 
Levodopa Chemical Properties
Melting point  276-278 °C (lit.)
alpha  -11.7 º (c=5.3, 1N HCl)
Boiling point  334.28°C (rough estimate)
density  1.3075 (rough estimate)
refractive index  -12 ° (C=5, 1mol/L HCl)
storage temp.  2-8°C
solubility  Slightly soluble in water, practically insoluble in ethanol (96 per cent). It is freely soluble in 1 M hydrochloric acid and sparingly soluble in 0.1 M hydrochloric acid .
form  Crystalline Powder
pka 2.32(at 25℃)
color  White to creamy
Water Solubility  Slightly soluble in water, dilute hydrochloric acid and formic acid. Insoluble in ethanol.
Merck  14,5464
BRN  2215169
Stability: Stable. Incompatible with strong oxidizing agents. Light and air sensitive.
InChIKey WTDRDQBEARUVNC-LURJTMIESA-N
CAS DataBase Reference 59-92-7(CAS DataBase Reference)
NIST Chemistry Reference Levodopa(59-92-7)
EPA Substance Registry System Levodopa (59-92-7)
 
Safety Information
Hazard Codes  Xn
Risk Statements  22-36/37/38-20/21/22
Safety Statements  26-36-24/25
WGK Germany  3
RTECS  AY5600000
10-23
TSCA  Yes
HS Code  29225090
Hazardous Substances Data 59-92-7(Hazardous Substances Data)
Toxicity LD50 in mice (mg/kg): 3650 ±327 orally, 1140 ±66 i.p., 450 ±42 i.v., >400 s.c.; in male, female rats (mg/kg): >3000, >3000 orally; 624, 663 i.p.; >1500, >1500 s.c. (Clark)
MSDS Information
Provider Language
Levodopa English
SigmaAldrich English
ACROS English
ALFA English
 
Levodopa Usage And Synthesis
Description The amino acid intermediate for the catecholamine neurotransmitters dopamine, norepinephrine, and epinephrine. It is formed by decarboxylation of tyrosine by the enzyme tyrosine hydroxylase, and its formation is the rate-limiting step in catecholamine biosynthesis. It is used therapeutically to treat idiopathic or chemical parkinsonism, often in combination with a  peripheral aromatic amino acid decarboxylase inhibitor and/or a direct-acting dopamine agonist.
Levodopa.jpg
Chemical Properties Colorless Crystalline Powder
Originator Larodopa,Roche,US,1970
Uses Natural isomer of the immediate precursor of dopamine; product of tyrsine hydroxylase
Uses antiparkinsonian
Uses An immediate precursor of dopamine and product of tyrosine hydroxylase.
Definition ChEBI: An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease
Manufacturing Process A charge of 1,000 g of ground velvet beans was extracted with 9 liters of 1% aqueous acetic acid at room temperature over a 20-hour period with occasional stirring during the first 4 hours. The liquor was decanted and thebean pulp slurry was vacuum filtered through a cake of acid-washed diatomaceous earth in a Buechner funnel. The decanted liquor was combined with the filtrate and concentrated under vacuum and a nitrogen atmosphere to a volume of 900 ml. After treating with acid-washed activated carbon, the concentrate was then filtered through acid-washed diatomaceous earth.
After concentrating the filtrate to approximately 400 ml, solids started crystallizing out at which time the filtrate was cooled by refrigerating at 5°C for several hours. Filtration gave 18.7 g of L-Dopa, MP 284° to 286°C (dec.); [α]D 8.81° (1% solution in aqueous 4% HCl). The infrared spectrum and paper chromatography indicated very good L-Dopa according to US Patent 3,253,023.
Various synthetic routes are also described by Kleeman and Engel.
Brand name Bendopa (Valeant); Dopar (Shire); Larodopa (Roche).
Therapeutic Function Antiparkinsonian
Biological Functions Levodopa (L-DOPA), the most reliable and effective drug used in the treatment of parkinsonism, can be considered a form of replacement therapy. Levodopa is the biochemical precursor of dopamine. It is used to elevate dopamine levels in the neostriatum of parkinsonian patients. Dopamine itself does not cross the blood-brain barrier and therefore has no CNS effects. However, levodopa, as an amino acid, is transported into the brain by amino acid transport systems, where it is converted to dopamine by the enzyme L-aromatic amino acid decarboxylase.
If levodopa is administered alone, it is extensively metabolized by L-aromatic amino acid decarboxylase in the liver, kidney, and gastrointestinal tract. To prevent this peripheral metabolism, levodopa is coadministered with carbidopa (Sinemet), a peripheral decarboxylase inhibitor. The combination of levodopa with carbidopa lowers the necessary dose of levodopa and reduces peripheral side effects associated with its administration.
Levodopa is widely used for treatment of all types of parkinsonism except those associated with antipsychotic drug therapy. However, as parkinsonism progresses, the duration of benefit from each dose of levodopa may shorten (wearing-off effect). Patients can also develop sudden, unpredictable fluctuations between mobility and immobility (on-off effect). In a matter of minutes, a patient enjoying normal or nearly normal mobility may suddenly develop a severe degree of parkinsonism. These symptoms are likely due to the progression of the disease and the loss of striatal dopamine nerve terminals.
General Description The first significant breakthrough in the treatment of PDcame about with the introduction of high-dose levodopa.Fahn referred to this as a revolutionary development intreating parkinsonian patients. The rationale for the use oflevodopa for the treatment of PD was established in theearly 1960s. Parkinsonian patients were shown to have decreasedstriatal levels of DA and reduced urinary excretionof DA. Since then, levodopa has shown to be remarkablyeffective for treating the symptoms of PD.Because ofenzymatic action of MAO-A in the gastrointestinal (GI)tract and AADC in the periphery, only a small percentage(1%–2%) of levodopa is delivered into the CNS.Coadministration of levodopa with the AADC inhibitor,carbidopa, prevents decarboxylation of levodopa outside ofthe CNS. The combination of levodopa and carbidopa resultsin a substantial increase in DA delivery to the CNSwith a decrease in peripheral side effects. Long-term therapywith levodopa leads to predictable motor complications.These include loss of efficacy before the next dose(“wearing off”), motor response fluctuations (“on/off”), andunwanted movements (dyskinesias).These effects arethought to be caused by the inability of levodopa therapyto restore normal DA levels in the CNS.As a result, theuse of longer-acting DA agonists may benefit parkinsonianpatients.
Biological Activity Immediate precursor of dopamine, produced by tyrosine hydroxylase. Displays antiParkinsonian activity.
Biochem/physiol Actions 3,4-Dihydroxy-L-phenylalanine or L-DOPA is a natural isomer of the immediate precursor of dopamine that crosses the blood-brain barrier. It is used for the treatment of Parkinson′s disease and is a product of tyrosine hydroxylase.
Pharmacology In a number of attempts to fix the deficit of dopamine in Parkinsonism, the introduction of a direct precursor of dopamine—levodopa—into the patient is considered a very logical therapy since levodopa diffuses across the blood–brain barrier, where it turns into dopamine and normalizes the level of dopamine. In this manner, levodopa stops or slows the development of Parkinsonism. Levodopa belongs to a group of the most effective drugs for treating the type of Parkinsonism not caused by medicinal agents.
Safety Profile Poison by ingestion. Moderately toxic by intravenous and intraperitoneal routes. Human systemic effects by ingestion: somnolence, hallucinations and distorted perceptions, toxic psychosis, motor activity changes, ataxia, dyspnea. Experimental teratogenic and reproductive effects. Questionable human carcinogen producing skin tumors. Human mutation data reported. An anticholinergic agent used as an anti Parhnsonian drug. When heated to decomposition it emits toxic fumes of NOx
Chemical Synthesis Levodopa, (-)-3-(3,4-dihydroxyphenyl)-L-alanine (10.1.1), is a levorotatory isomer of dioxyphenylalanine used as a precursor of dopamine. There are a few ways of obtaining levodopa using a semisynthetic approach, which consists of the microbiological hydroxylation of L-tyrosine (10.1.1), as well as implementing a purely synthetic approach.
Oxidation of L-tyrosine, for selective introduction of a hydroxyl group at C3 of the tyrosine ring, can be accomplished in a purely synthetic manner by using a mixture of hydrogen peroxide and iron(II) sulfate mixture in water as an oxidant with permanent presence of oxygen.

The third method of levodopa synthesis consists of the acetylation of tyrosine using acetylchloride in the presence of aluminum chloride and the subsequent oxidative deacylation of the formed 3-acetyltyrosine (10.1.2) using hydrogen peroxide in sodium hydroxide solution.
Purification Methods Likely impurities are vanillin, hippuric acid, 3-methoxytyrosine and 3-aminotyrosine. DOPA recrystallises from large volumes of H2O forming colourless white needles; its solubility in H2O is 0.165%, but it is insoluble in EtOH, *C6H6, CHCl3, and EtOAc. Also crystallise it by dissolving it in dilute HCl and adding dilute ammonia to give pH 5, under N2. Alternatively, crystallise it from dilute aqueous EtOH. It is rapidly oxidised in air when moist, and darkens, particularly in alkaline solution. Dry it in vacuo at 70o in the dark, and store it in a dark container preferably under N2. It has at 220.5nm (log 3.79) and 280nm (log 3.42) in 0.001N max HCl. [Yamada et al. Chem Pharm Bull Jpn 10 693 1962, Bretschneider et al. Helv Chim Acta 56 2857 1973, NMR: Jardetzky & Jardetzky J Biol Chem 233 383 1958, Beilstein 4 IV 2492, 2493.]
 
Levodopa Preparation Products And Raw materials
Raw materials Mesitylene-->L-Tyrosine-->Cation exchange resin,strong acidic styrene-->Sepia (dye)-->1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHORIC ACID SODIUM SALT-->Acetic acid
Preparation Products (S)-(-)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID HYDROCHLORIDE-->N-(tert-buloxycarbonyl)-3,4-dihydroxy-L-phenylalanine-->(S)-Methyl 2-((tert-butoxycarbonyl)aMino)-3-(3,4-dihydroxyphenyl)propanoate-->5,6-dihydroxy-1H-indole-2-carboxylic acid-->Tetrahydropapaveroline-->FMOC-DOPA(ACETONIDE)-OH-->L-3,4-DIHYDROXYPHENYLALANINE METHYL ESTER HYDROCHLORIDE
 
 
 
 
 

 

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Leader Biochemical Group is a large leader incorporated industry manufacturers and suppliers of advanced refined raw materials From the year of 1996 when our factory was put into production to year of 2020, our group has successively invested in more than 52 factories with shares and subordinates.We focus on manufacture Pharm & chemicals, functional active ingredients, nutritional Ingredients, health care products, cosmetics, pharmaceutical and refined feed, oil, natural plant ingredients industries to provide top quality of GMP standards products.All the invested factories' product lines cover API and intermediates, vitamins, amino acids, plant extracts, daily chemical products, cosmetics raw materials, nutrition and health care products, food additives, feed additives, essential oil products, fine chemical products and agricultural chemical raw materials And flavors and fragrances. Especially in the field of vitamins, amino acids, pharmaceutical raw materials and cosmetic raw materials, we have more than 20 years of production and sales experience. All products meet the requirements of high international export standards and have been recognized by customers all over the world. Our manufacture basement & R&D center located in National Aerospace Economic & Technical Development Zone Xi`an Shaanxi China. Now not only relying on self-cultivation and development as well as maintains good cooperative relations with many famous research institutes and universities in China. Now, we have closely cooperation with Shanghai Institute of Organic Chemistry of Chinese Academy of Science, Beijing Institute of Material Medical of Chinese Academy of Medical Science, China Pharmaceutical University, Zhejiang University. Closely cooperation with them not only integrating Science and technology resources, but also increasing the R&D speed and improving our R&D power. Offering Powerful Tech supporting Platform for group development. Keep serve the manufacture and the market as the R&D central task, focus on the technical research.  Now there are 3 technology R & D platforms including biological extract, microorganism fermentation and chemical synthesis, and can independently research and develop kinds of difficult APIs and pharmaceutical intermediates. With the strong support of China State Institute of Pharmaceutical Industry (hereinafter short for CSIPI), earlier known as Shanghai Institute of Pharmaceutical Industry (SIPI), we have unique advantages in the R & D and industrialization of high-grade, precision and advanced products.  Now our Group technical force is abundant, existing staff more that 1000 people, senior professional and technical staff accounted for more than 50% of the total number of employees, including 15 PhD research and development personnel, 5 master′ S degree in technical and management personnel 9 people. We have advanced equipment like fermentation equipment and technology also extraction, isolation, purification, synthesis with rich production experience and strict quality control system, According to the GMP required, quickly transforming the R&D results to industrial production in time, it is our advantages and our products are exported to North and South America, Europe, Middle East, Africa, and other five continents and scale the forefront in the nation, won good international reputation.  We believe only good quality can bring good cooperation, quality is our key spirit during our production, we are warmly welcome clients and partner from all over the world contact us for everlasting cooperation, Leader will be your strong, sincere and reliable partner in China.

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Levodopa Basic information
Product Name: Levodopa
Synonyms: 2-amino-3-(3,4-dihydroxyphenyl)propanoicacid;3,4-Dihydroxyphenylalanine(form2);3,4-Dihydroxyphenyl-L-alanine;3,4-DIHYDROXY-L-PHENYLALANINE;3,4-L-DIHYDROXYPHENYLALANINE;3-(3,4-DIHYDROXYPHENYL)-L-ALANINE;3-HYDROXY-L-TYROSINE;BETA-(3,4-DIHYDROXYPHENYL)-L-ALANINE
CAS: 59-92-7
MF: C9H11NO4
MW: 197.19
EINECS: 200-445-2
Product Categories: Inhibitors;plant extract;Amino Acids;Biochemistry;Biological-modified Amino Acids;Dopamine receptor;Pharmaceutical;Nutritional Supplements;Natural Plant Extract;Amino Acids & Derivatives;Chiral Reagents;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals;Plant extracts;Herb extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;LARADOPA
Mol File: 59-92-7.mol
Levodopa Structure
 
Levodopa Chemical Properties
Melting point  276-278 °C (lit.)
alpha  -11.7 º (c=5.3, 1N HCl)
Boiling point  334.28°C (rough estimate)
density  1.3075 (rough estimate)
refractive index  -12 ° (C=5, 1mol/L HCl)
storage temp.  2-8°C
solubility  Slightly soluble in water, practically insoluble in ethanol (96 per cent). It is freely soluble in 1 M hydrochloric acid and sparingly soluble in 0.1 M hydrochloric acid .
form  Crystalline Powder
pka 2.32(at 25℃)
color  White to creamy
Water Solubility  Slightly soluble in water, dilute hydrochloric acid and formic acid. Insoluble in ethanol.
Merck  14,5464
BRN  2215169
Stability: Stable. Incompatible with strong oxidizing agents. Light and air sensitive.
InChIKey WTDRDQBEARUVNC-LURJTMIESA-N
CAS DataBase Reference 59-92-7(CAS DataBase Reference)
NIST Chemistry Reference Levodopa(59-92-7)
EPA Substance Registry System Levodopa (59-92-7)
 
Safety Information
Hazard Codes  Xn
Risk Statements  22-36/37/38-20/21/22
Safety Statements  26-36-24/25
WGK Germany  3
RTECS  AY5600000
10-23
TSCA  Yes
HS Code  29225090
Hazardous Substances Data 59-92-7(Hazardous Substances Data)
Toxicity LD50 in mice (mg/kg): 3650 ±327 orally, 1140 ±66 i.p., 450 ±42 i.v., >400 s.c.; in male, female rats (mg/kg): >3000, >3000 orally; 624, 663 i.p.; >1500, >1500 s.c. (Clark)
MSDS Information
Provider Language
Levodopa English
SigmaAldrich English
ACROS English
ALFA English
 
Levodopa Usage And Synthesis
Description The amino acid intermediate for the catecholamine neurotransmitters dopamine, norepinephrine, and epinephrine. It is formed by decarboxylation of tyrosine by the enzyme tyrosine hydroxylase, and its formation is the rate-limiting step in catecholamine biosynthesis. It is used therapeutically to treat idiopathic or chemical parkinsonism, often in combination with a  peripheral aromatic amino acid decarboxylase inhibitor and/or a direct-acting dopamine agonist.
Levodopa.jpg
Chemical Properties Colorless Crystalline Powder
Originator Larodopa,Roche,US,1970
Uses Natural isomer of the immediate precursor of dopamine; product of tyrsine hydroxylase
Uses antiparkinsonian
Uses An immediate precursor of dopamine and product of tyrosine hydroxylase.
Definition ChEBI: An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease
Manufacturing Process A charge of 1,000 g of ground velvet beans was extracted with 9 liters of 1% aqueous acetic acid at room temperature over a 20-hour period with occasional stirring during the first 4 hours. The liquor was decanted and thebean pulp slurry was vacuum filtered through a cake of acid-washed diatomaceous earth in a Buechner funnel. The decanted liquor was combined with the filtrate and concentrated under vacuum and a nitrogen atmosphere to a volume of 900 ml. After treating with acid-washed activated carbon, the concentrate was then filtered through acid-washed diatomaceous earth.
After concentrating the filtrate to approximately 400 ml, solids started crystallizing out at which time the filtrate was cooled by refrigerating at 5°C for several hours. Filtration gave 18.7 g of L-Dopa, MP 284° to 286°C (dec.); [α]D 8.81° (1% solution in aqueous 4% HCl). The infrared spectrum and paper chromatography indicated very good L-Dopa according to US Patent 3,253,023.
Various synthetic routes are also described by Kleeman and Engel.
Brand name Bendopa (Valeant); Dopar (Shire); Larodopa (Roche).
Therapeutic Function Antiparkinsonian
Biological Functions Levodopa (L-DOPA), the most reliable and effective drug used in the treatment of parkinsonism, can be considered a form of replacement therapy. Levodopa is the biochemical precursor of dopamine. It is used to elevate dopamine levels in the neostriatum of parkinsonian patients. Dopamine itself does not cross the blood-brain barrier and therefore has no CNS effects. However, levodopa, as an amino acid, is transported into the brain by amino acid transport systems, where it is converted to dopamine by the enzyme L-aromatic amino acid decarboxylase.
If levodopa is administered alone, it is extensively metabolized by L-aromatic amino acid decarboxylase in the liver, kidney, and gastrointestinal tract. To prevent this peripheral metabolism, levodopa is coadministered with carbidopa (Sinemet), a peripheral decarboxylase inhibitor. The combination of levodopa with carbidopa lowers the necessary dose of levodopa and reduces peripheral side effects associated with its administration.
Levodopa is widely used for treatment of all types of parkinsonism except those associated with antipsychotic drug therapy. However, as parkinsonism progresses, the duration of benefit from each dose of levodopa may shorten (wearing-off effect). Patients can also develop sudden, unpredictable fluctuations between mobility and immobility (on-off effect). In a matter of minutes, a patient enjoying normal or nearly normal mobility may suddenly develop a severe degree of parkinsonism. These symptoms are likely due to the progression of the disease and the loss of striatal dopamine nerve terminals.
General Description The first significant breakthrough in the treatment of PDcame about with the introduction of high-dose levodopa.Fahn referred to this as a revolutionary development intreating parkinsonian patients. The rationale for the use oflevodopa for the treatment of PD was established in theearly 1960s. Parkinsonian patients were shown to have decreasedstriatal levels of DA and reduced urinary excretionof DA. Since then, levodopa has shown to be remarkablyeffective for treating the symptoms of PD.Because ofenzymatic action of MAO-A in the gastrointestinal (GI)tract and AADC in the periphery, only a small percentage(1%–2%) of levodopa is delivered into the CNS.Coadministration of levodopa with the AADC inhibitor,carbidopa, prevents decarboxylation of levodopa outside ofthe CNS. The combination of levodopa and carbidopa resultsin a substantial increase in DA delivery to the CNSwith a decrease in peripheral side effects. Long-term therapywith levodopa leads to predictable motor complications.These include loss of efficacy before the next dose(“wearing off”), motor response fluctuations (“on/off”), andunwanted movements (dyskinesias).These effects arethought to be caused by the inability of levodopa therapyto restore normal DA levels in the CNS.As a result, theuse of longer-acting DA agonists may benefit parkinsonianpatients.
Biological Activity Immediate precursor of dopamine, produced by tyrosine hydroxylase. Displays antiParkinsonian activity.
Biochem/physiol Actions 3,4-Dihydroxy-L-phenylalanine or L-DOPA is a natural isomer of the immediate precursor of dopamine that crosses the blood-brain barrier. It is used for the treatment of Parkinson′s disease and is a product of tyrosine hydroxylase.
Pharmacology In a number of attempts to fix the deficit of dopamine in Parkinsonism, the introduction of a direct precursor of dopamine—levodopa—into the patient is considered a very logical therapy since levodopa diffuses across the blood–brain barrier, where it turns into dopamine and normalizes the level of dopamine. In this manner, levodopa stops or slows the development of Parkinsonism. Levodopa belongs to a group of the most effective drugs for treating the type of Parkinsonism not caused by medicinal agents.
Safety Profile Poison by ingestion. Moderately toxic by intravenous and intraperitoneal routes. Human systemic effects by ingestion: somnolence, hallucinations and distorted perceptions, toxic psychosis, motor activity changes, ataxia, dyspnea. Experimental teratogenic and reproductive effects. Questionable human carcinogen producing skin tumors. Human mutation data reported. An anticholinergic agent used as an anti Parhnsonian drug. When heated to decomposition it emits toxic fumes of NOx
Chemical Synthesis Levodopa, (-)-3-(3,4-dihydroxyphenyl)-L-alanine (10.1.1), is a levorotatory isomer of dioxyphenylalanine used as a precursor of dopamine. There are a few ways of obtaining levodopa using a semisynthetic approach, which consists of the microbiological hydroxylation of L-tyrosine (10.1.1), as well as implementing a purely synthetic approach.
Oxidation of L-tyrosine, for selective introduction of a hydroxyl group at C3 of the tyrosine ring, can be accomplished in a purely synthetic manner by using a mixture of hydrogen peroxide and iron(II) sulfate mixture in water as an oxidant with permanent presence of oxygen.

The third method of levodopa synthesis consists of the acetylation of tyrosine using acetylchloride in the presence of aluminum chloride and the subsequent oxidative deacylation of the formed 3-acetyltyrosine (10.1.2) using hydrogen peroxide in sodium hydroxide solution.
Purification Methods Likely impurities are vanillin, hippuric acid, 3-methoxytyrosine and 3-aminotyrosine. DOPA recrystallises from large volumes of H2O forming colourless white needles; its solubility in H2O is 0.165%, but it is insoluble in EtOH, *C6H6, CHCl3, and EtOAc. Also crystallise it by dissolving it in dilute HCl and adding dilute ammonia to give pH 5, under N2. Alternatively, crystallise it from dilute aqueous EtOH. It is rapidly oxidised in air when moist, and darkens, particularly in alkaline solution. Dry it in vacuo at 70o in the dark, and store it in a dark container preferably under N2. It has at 220.5nm (log 3.79) and 280nm (log 3.42) in 0.001N max HCl. [Yamada et al. Chem Pharm Bull Jpn 10 693 1962, Bretschneider et al. Helv Chim Acta 56 2857 1973, NMR: Jardetzky & Jardetzky J Biol Chem 233 383 1958, Beilstein 4 IV 2492, 2493.]
 
Levodopa Preparation Products And Raw materials
Raw materials Mesitylene-->L-Tyrosine-->Cation exchange resin,strong acidic styrene-->Sepia (dye)-->1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHORIC ACID SODIUM SALT-->Acetic acid
Preparation Products (S)-(-)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID HYDROCHLORIDE-->N-(tert-buloxycarbonyl)-3,4-dihydroxy-L-phenylalanine-->(S)-Methyl 2-((tert-butoxycarbonyl)aMino)-3-(3,4-dihydroxyphenyl)propanoate-->5,6-dihydroxy-1H-indole-2-carboxylic acid-->Tetrahydropapaveroline-->FMOC-DOPA(ACETONIDE)-OH-->L-3,4-DIHYDROXYPHENYLALANINE METHYL ESTER HYDROCHLORIDE

 

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