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Levodopa

Product Name
Levodopa
CAS No.
59-92-7
Chemical Name
Levodopa
Synonyms
L-DOPA;3,4-DIHYDROXY-L-PHENYLALANINE;L-3,4-DIHYDROXYPHENYLALANINE;DIHYDROXYPHENYLALANINE;L-Dihydroxyphenylalanine;Levedopa;Dopar;Bendopa;Larodopa;3-HYDROXY-L-TYROSINE
CBNumber
CB2402938
Molecular Formula
C9H11NO4
Formula Weight
197.19
MOL File
59-92-7.mol
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Levodopa Property

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 .
pka
2.32(at 25℃)
form 
Crystalline Powder
color 
White to creamy
Odor
at 100.00 %. odorless
Odor Type
odorless
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
LogP
-1.154 (est)
CAS DataBase Reference
59-92-7(CAS DataBase Reference)
NIST Chemistry Reference
Levodopa(59-92-7)
EPA Substance Registry System
Levodopa (59-92-7)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D9628
Product name
3,4-Dihydroxy-L-phenylalanine
Purity
≥98% (TLC)
Packaging
5g
Price
$76
Updated
2024/03/01
Sigma-Aldrich
Product number
BP213
Product name
Levodopa
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$269
Updated
2024/03/01
Sigma-Aldrich
Product number
72816
Product name
3,4-Dihydroxy-L-phenylalanine
Purity
certified reference material, TraceCERT?
Packaging
50MG
Price
$168
Updated
2024/03/01
Sigma-Aldrich
Product number
1361009
Product name
Levodopa
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
D0600
Product name
3-(3,4-Dihydroxyphenyl)-L-alanine
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$36
Updated
2024/03/01
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Levodopa Chemical Properties,Usage,Production

Description

Levodopa is an amino acid precursor of dopamine with antiparkinsonian properties. Levodopa is a prodrug that is converted to dopamine by DOPA decarboxylase and can cross the blood-brain barrier. When in the brain, levodopa is decarboxylated to dopamine and stimulates the dopaminergic receptors, thereby compensating for the depleted supply of endogenous dopamine seen in Parkinson's disease. To assure that adequate concentrations of levodopa reach the central nervous system, it is administered with carbidopa, a decarboxylase inhibitor that does not cross the blood-brain barrier, thereby diminishing the decarboxylation and inactivation of levodopa in peripheral tissues and increasing the delivery of dopamine to the CNS.

Chemical Properties

L-Dopa [59-92-7], levodopa, crystallizes as colorless, odorless, and tasteless needles from water, mp 276-278℃(decomp.). It is freely soluble in dilute hydrochloric and formic acids but practically insoluble in ethanol, benzene, chloroform, and ethyl acetate. Solubility in water is 66 mg/40 mL. In the presence of moisture, l-dopa is rapidly oxidized by atmospheric oxygen, with darkening.

Originator

Larodopa,Roche,US,1970

Uses

Levodopa is an immediate precursor of dopamine and product of tyrosine hydroxylase. It derived from vanillin is widely used for treatment of Parkinson’s disease, most often in combination with peripheral decarboxylase inhibitors such as benserazide and carbidopa.

Definition

ChEBI: Levodopa is 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

Levodopa can be prepared from 1-3-dinitrotyrosine, 3-(3,4-methylenedioxyphenyl)-l-alanine, and l-tyrosine, and by fermentation of l-tyrosine.
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.

General Description

Levodopa belongs to a group of the most effective drugs for treating the type of Parkinsonism not caused by medicinal agents. 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.

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.

Side effects

Get medical help immediately if you have any symptoms: fever, unusual muscle stiffness, severe confusion, sweating, fast/irregular heartbeat, and rapid breathing. A severe allergic reaction to this drug is rare. This medication may cause saliva, urine, or sweat to turn dark. This effect is harmless.

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

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.

Metabolism

Metabolism of levodopa and dopamine may proceed by four pathways: decarboxylation, O-methylation, transamination, and oxidation. Levodopa is decarboxylated to dopamine by the enzyme AAAD. This enzyme is ubiquitously distributed in the gut, liver, and kidney. The gastric and intestinal wall contains AAAD, which significantly metabolizes levodopa. At least half of an oral levodopa dose is decarboxylated during absorption and first-pass hepatic metabolism. Further decarboxylation may occur by AAADC during successive circulation through these tissues. Approximately 70% of the levodopa metabolites appear as dopamine and its degradation products, indicating that decarboxylation is the primary route of metabolism.

storage

-20°C

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.]

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Levodopa Suppliers

Vertexyn (Nanjing) Bioworks Co., Ltd.
Tel
025-58822206 18020175818
Email
sales@vertexynbio.com
Country
China
ProdList
10
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58
Changxing Pharmaceutical Co., Ltd.
Tel
0572-6236833 13905823060
Fax
0572-6236733
Email
jianjian6602@163.com
Country
China
ProdList
15
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58
Shaanxi xinmaoyuan Agricultural Development Co., Ltd
Tel
029-32565555 15596477170
Fax
3002805869
Email
3002805869@qq.com
Country
China
ProdList
744
Advantage
58
Shaanxi Pioneer Biotech Co.,Ltd.
Tel
029-84385017-8011 15202491660
Fax
QQ3502078241
Email
sales8@pioneerbiotech.com
Country
China
ProdList
484
Advantage
58
Huzhou Shuobang Biotechnology Co., LTD
Tel
13732389004
Email
meshelmeshel@163.com
Country
China
ProdList
24
Advantage
58
Chengdu Chenlv Herb Co., Ltd.
Tel
028-88523492 15528171243
Email
chenrongpharma@126.com
Country
China
ProdList
124
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40241
Advantage
62
INTATRADE GmbH
Tel
+49 3493/605464
Fax
+49 3493/605470
Email
sales@intatrade.de
Country
Germany
ProdList
3576
Advantage
66
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15848
Advantage
69
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View Lastest Price from Levodopa manufacturers

Sinoway Industrial co., ltd.
Product
Levodopa 59-92-7
Price
US $120.00-85.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
0.99
Supply Ability
20 tons
Release date
2023-11-21
Hong Kong Excellence Biotechnology Co., Ltd.
Product
Levodopa 59-92-7
Price
US $100.00/kg
Min. Order
1kg
Purity
99.80%
Supply Ability
20tons
Release date
2023-10-11
Hong Kong Excellence Biotechnology Co., Ltd.
Product
Levodopa 59-92-7
Price
US $100.00/kg
Min. Order
1kg
Purity
>99%
Supply Ability
20tons
Release date
2023-10-12

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