ChemicalBook > CAS DataBase List > Levodopa

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
More
Less

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
optical activity
-39.5 (H2O) -12.025 (1 mol dm-3 HCl)
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)
More
Less

Safety

Hazard Codes 
Xn
Risk Statements 
22-36/37/38-20/21/22
Safety Statements 
26-36-24/25
WGK Germany 
3
RTECS 
AY5600000
F 
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)
More
Less

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.

More
Less

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
More
Less

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.]

Levodopa Preparation Products And Raw materials

Raw materials

Cation exchange resin,strong acidic styrene L-Tyrosine Sepia (dye) Mesitylene 1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHORIC ACID SODIUM SALT

Preparation Products

(S)-(-)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID HYDROCHLORIDE
More
Less

Levodopa Suppliers

Americas 1 Belgium 1 Canada 1 China 641 Europe 3 France 2 Germany 6 India 34 Israel 1 Japan 8 Singapore 1 Switzerland 1 United Kingdom 14 United States 62 Global 777
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
Advantage
62
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
Advantage
58
HBCChem, Inc.
Tel
+1-510-219-6317
Fax
+1-650-486-1361
Email
sales@hbcchem.com
Country
United States
ProdList
10648
Advantage
60
EMMX Biotechnology LLC
Tel
888-539-0666
Fax
888-539-0666
Email
info@emmx.com
Country
United States
ProdList
8447
Advantage
60
Target molecule Corp.
Tel
857-239-0968
Fax
857-239-8801
Email
service1@targetmol.com
Country
United States
ProdList
2559
Advantage
60
Alfa Chemistry
Tel
Fax
1-516-927-0118
Email
Info@alfa-chemistry.com
Country
United States
ProdList
24072
Advantage
58
TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32165
Advantage
58
InvivoChem
Tel
+1-708-310-1919 +1-13798911105
Fax
708-557-7486
Email
sales@invivochem.cn
Country
United States
ProdList
6391
Advantage
58
BOC Sciences
Tel
+1-631-485-4226
Fax
1-631-614-7828
Email
inquiry@bocsci.com
Country
United States
ProdList
19553
Advantage
58
TargetMol Chemicals Inc.
Tel
+8613564774135
Email
zijue.cai@tsbiochem.com
Country
United States
ProdList
19885
Advantage
58
TargetMol Chemicals Inc.
Tel
Email
support@targetmol.com
Country
United States
ProdList
38632
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
52925
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
Protheragen-ING
Tel
+16313385890
Email
info@protheragen-ing.com
Country
United States
ProdList
3868
Advantage
58
Aceschem Inc.
Tel
+1-817863-6948 +1-（817）863-6948
Email
sales@aceschem.com
Country
United States
ProdList
19632
Advantage
58
United States Biological
Tel
--
Fax
--
Email
sales@advtechind.com
Country
United States
ProdList
6075
Advantage
58
ApexBio Technology
Tel
--
Fax
--
Email
sales@apexbt.com
Country
United States
ProdList
6251
Advantage
58
Genabolix Laboratory, Inc.
Tel
--
Fax
--
Email
info@genabolix.com
Country
United States
ProdList
51
Advantage
0
Acros Organics USA
Tel
--
Fax
--
Email
eveleth@fisherchem.com
Country
United States
ProdList
3846
Advantage
81
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
Ajinomoto AminoScience LLC
Tel
--
Fax
--
Email
aminoacid-sales@ajiusa.com
Country
United States
ProdList
45
Advantage
65
Glentham Life Sciences Ltd
Tel
--
Fax
--
Email
info@glentham.com
Country
United States
ProdList
2026
Advantage
58
Jiangyin Healthway International Trade Co., Ltd
Tel
--
Fax
--
Email
info@healthwaychem.com
Country
United States
ProdList
1006
Advantage
58
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
SynQuest Laboratories, Inc.
Tel
--
Fax
--
Email
info@synquestlabs.com
Country
United States
ProdList
6871
Advantage
62
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
TCI America
Tel
--
Fax
--
Email
sales@tciamerica.com
Country
United States
ProdList
6909
Advantage
75
Frontier Scientific, Inc.
Tel
--
Fax
--
Email
sales@frontiersci.com
Country
United States
ProdList
6222
Advantage
86
Santa Cruz Biotechnology, Inc.
Tel
--
Fax
--
Email
scbt@scbt.com
Country
United States
ProdList
3597
Advantage
60
Sisco Research Laboratories Pvt. Ltd.
Tel
--
Fax
--
Email
srlmarketing@dishnetdsl.net
Country
United States
ProdList
1905
Advantage
64
HBCChem Inc.
Tel
--
Fax
--
Email
sales@hbcchem-inc.com
Country
United States
ProdList
4569
Advantage
30
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6962
Advantage
56
Waterstone Technology, LLC
Tel
--
Fax
--
Email
sales@waterstonetech.com
Country
United States
ProdList
6786
Advantage
30
AlliChem, LLC
Tel
--
Fax
--
Email
sales@allichemllc.com
Country
United States
ProdList
6516
Advantage
60
Combi-Blocks Inc.
Tel
--
Fax
--
Email
sales@combi-blocks.com
Country
United States
ProdList
6618
Advantage
69
Beta Pharma, Inc.
Tel
--
Fax
--
Email
sales@betapharma.com
Country
United States
ProdList
6226
Advantage
60
Alfa Aesar
Tel
--
Fax
--
Email
tech@alfa.com
Country
United States
ProdList
6814
Advantage
81
Sinova Inc.
Tel
--
Fax
--
Email
sales@sinovainc.com
Country
United States
ProdList
4009
Advantage
58
Naugra Export
Tel
--
Fax
--
Country
United States
ProdList
1332
Advantage
47
2A PharmaChem USA
Tel
--
Fax
--
Email
sales@2apharmachem.com
Country
United States
ProdList
6137
Advantage
39
Altan Corporation
Tel
--
Fax
--
Email
OrderingService@AltanBiochemicals.com
Country
United States
ProdList
1161
Advantage
30
HONEST JOY HOLDINGS LIMITED
Tel
--
Fax
--
Email
sales@honestjoy.cn
Country
United States
ProdList
6675
Advantage
54
Aceto Corporation
Tel
--
Fax
--
Email
contact@aceto.com
Country
United States
ProdList
2619
Advantage
75
Advance Scientific & Chemical
Tel
--
Fax
--
Email
sales@advance-scientific.com
Country
United States
ProdList
6419
Advantage
71
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
Ajinomoto AminoScience LLC
Tel
--
Fax
--
Email
sales@ajiaminoacids.com
Country
United States
ProdList
36
Advantage
55
NetQem
Tel
--
Fax
--
Email
sales@netqem.us
Country
United States
ProdList
1641
Advantage
38
Loba Chemie Pvt. Ltd.
Tel
--
Fax
--
Country
United States
ProdList
1945
Advantage
71
Medical Isotopes
Tel
--
Fax
--
Email
stohler@medicalisotopes.com
Country
United States
ProdList
6181
Advantage
68
More
Less

View Lastest Price from Levodopa manufacturers

HangZhou RunYan Pharma Technology Co.,LTD.
Product
Levodopa 59-92-7
Price
US $0.00-0.00/g
Min. Order
10g
Purity
99% HPLC
Supply Ability
10000
Release date
2024-09-20
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Levodopa 59-92-7
Price
US $999.00-666.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-20
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Levodopa 59-92-7
Price
US $180.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-04-23

59-92-7, LevodopaRelated Search:

Boc-D-Tyr-OH TYROSINASE L-carnitine L-Alanine Levamisole Methyldopa L-Tyrosine H-ARG-ARG-LEU-ILE-GLU-ASP-ASN-GLU-TYR-THR-ALA-ARG-GLY-OH Phenibut 4-Ethoxy-N,N,N-trimethyl-4-oxo-1-butanaminium chloride Guanidineacetic acid L(-)-Carvone L(-)-Carnitine hydrochloride L-Carnitine fumarate Levosulpiride L-Carnitine-L-tartrate Levofloxacin carboxylic acid (R)-(-)-Epichlorohydrin

  • 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
  • HYDROXYTYROSINE
  • H-PHE(3,4-DI-HYDROXY)-OH
  • H-PHE(3,4-DI-OH)-OH
  • H-TYR(3-HYDROXY)-OH
  • L-BETA-(3,4-DIHYDROXYPHENYL)ALANINE
  • L-DOPA
  • L-DOPA, L-3-HYDROXYTYROSINE
  • LEVODOPA
  • L-3-(3,4-DIHYDROXYPHENYL)ALANINE
  • L-3,4-DIHYDROXYPHENYLALANINE
  • L-3-HYDROXYTYROSINE
  • DIHYDROXYPHENYLALANINE
  • DOPA, L-
  • 3,4-Dihydroxy-l-phenylalanine 96%
  • 3-（3,4-Dihydroxyphenyl）-L-alanine [Levodopa]
  • H-Tyr(3-OH)-OH
  • L-DOPA 3,4-L-Dihydroxyphenylalanine
  • L-DOPA, 99% (L-3,4-DIHYDROXYPHENYLALANINE) (99% EE/GLC)
  • L-Dihydroxyphenylalanine
  • Ro 4-6316
  • ro4-6316
  • sobiodopa
  • Syndopa
  • Veldopa
  • Weldopa
  • l-3,4-dihydroxyphenyl-alpha-alanine
  • l-alpha-dihydroxyphenylalanine
  • Laradopa
  • Larodopa
  • 3-hydroxy-l-tyrosin
  • 4-dihydroxyphenyl)-3-((-)-alanin
  • 4-dihydroxyphenyl)-3-(l-alanin
  • Alanine, 3-(3,4-dihydroxyphenyl)-
  • Alanine, 3-(3,4-dihydroxyphenyl)-, L-
  • Beldopa
  • Bendopa
  • beta-(3,4-dihydrophenyl)-l-alanine
  • beta-(3,4-Dihydroxyphenyl)alanine
  • beta-(3,4-dihydroxyphenyl)-alpha-alanine
  • biodopa
  • BrocaadopaLarodopa
  • Brocadopa
  • cerepap
  • cerepar
  • Cidandopa
  • component of Madopa, sinemet
  • component of Sinemet
  • Deadopa
  • Dihydroxy-L-phenylalanine
  • Dopaflex