ChemicalBook > CAS DataBase List > S-(-)-Carbidopa

S-(-)-Carbidopa

Product Name
S-(-)-Carbidopa
CAS No.
28860-95-9
Chemical Name
S-(-)-Carbidopa
Synonyms
S(-)-CARBIDOPA;mk486;KINSON;L-3-(3,4;Carbidopa-d3;(S)-CARBIDOPA;CARBIDOPA EDMF;n-aminomethyldopa;CARBIDOPAANHYDROUS;CarbidopaUsp28/Ep5
CBNumber
CB5738078
Molecular Formula
C10H14N2O4
Formula Weight
226.23
MOL File
28860-95-9.mol
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S-(-)-Carbidopa Property

Melting point:
203-205° (dec); mp 208°
alpha 
D -17.3° (methanol)
Boiling point:
367.84°C (rough estimate)
Density 
1.2616 (rough estimate)
refractive index 
1.5000 (estimate)
storage temp. 
-20°C
solubility 
DMSO (Slightly), Methanol (Slightly)
pka
3.40±0.14(Predicted)
form 
powder
color 
White to Off-White
Stability:
Unstable in Solution
CAS DataBase Reference
28860-95-9(CAS DataBase Reference)
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Safety

WGK Germany 
3
RTECS 
MW5298000
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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.

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
C1335
Product name
S-(?)-Carbidopa
Purity
≥98% (TLC), powder
Packaging
25mg
Price
$115
Updated
2024/03/01
Sigma-Aldrich
Product number
C1335
Product name
S-(?)-Carbidopa
Purity
≥98% (TLC), powder
Packaging
100mg
Price
$345
Updated
2024/03/01
Cayman Chemical
Product number
23783
Product name
Carbidopa
Purity
≥98%
Packaging
25mg
Price
$25
Updated
2021/12/16
Cayman Chemical
Product number
23783
Product name
Carbidopa
Purity
≥98%
Packaging
50mg
Price
$48
Updated
2021/12/16
Cayman Chemical
Product number
23783
Product name
Carbidopa
Purity
≥98%
Packaging
100mg
Price
$90
Updated
2021/12/16
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S-(-)-Carbidopa Chemical Properties,Usage,Production

Chemical Properties

White Solid

Originator

Sinemet,Merck Sharp and Dohme,Italy,1974

Uses

in combinaison with levodopa as antiparkinsonian;inhibits aromatic-L-amino-acid decarboxylase (DOPA Decarboxylase or DDC)

Uses

(S)-(-)-Carbidopa is a peripheral decarboxylase inhibitor that is commonly used in combination with L-DOPA (D533751) for treatment of Parkinsonism. S(-)-Carbidopa ( has also been shown to prolong the elimination half-life of L-DOPA from blood plasma and skeletal muscle.

Definition

ChEBI: 3-(3,4-Dihydroxyphenyl)propanoic acid in which the hydrogens alpha- to the carboxyl group are substituted by hydrazinyl and methyl groups (S-configuration). Carbidopa is a dopa decarboxylase inhibitor, so prevents conversi n of levodopa to dopamine. It has no antiparkinson activity by itself, but is used (commonly as its hydrate) in the management of Parkinson's disease to reduce peripheral adverse effects of levodopa.

Manufacturing Process

To a solution of vanillin in toluene is added nitroethane, butylamine and glacial acetic acid. The mixture is refluxed and the water of reaction is steadily azeotropically removed by distillation. After the theoretical amount of water is distilled out, distillation is continued to remove excess reactants. The last trace of excess reactants is then removed at room temperature under a vacuum. The product is then triturated with a hydrocarbon solvent such as Skellysolve B and is thus obtained in a crystalline state. In general, however, it is preferred to dissolve the residue directly in toluene for use in the next step, without isolating the 1-(2-nitropropen-1-yl)-4-hydroxy-3- methoxybenzene.
A mixture of iron, ferric chloride and water is added to the toluene solution. The mixture is heated to reflux and concentrated hydrochloric acid is added dropwise at a rate calculated to keep the mixture refluxing vigorously. After the hydrochloric acid is all added, the refluxing is continued by the application of heat for several hours. A siliceous filter aid is then added to the cooled reaction mixture and the material is removed by filtration. The filter cake is washed four times, each time with 90 ml of benzene. The organic layer is then separated from the filtrate. The water layer is acidified to a pH of 2 and extracted three times with 90 ml portions of benzene.
These extracts are then combined with the organic solvent layer and the combined organic phase is extracted four times with 100 ml portions of water. It is then stirred for an hour with 230 ml of 10% sodium bisulfite solution. The organic solvent phase is then separated, washed seven times with 100 ml portions of water and dried over magnesium sulfate. Evaporation of the solvent gives 1-(4-hydroxy-3-methoxyphenyl)-2-propanone in the form of an oil.
A mixture of 59.5 g of that oily product, 1.85 liters of benzene and 1 kg of potassium bisulfite in 200 liters of water is stirred at room temperature for two hours. The precipitated bisulfite addition product of the ketone is isolated by filtration and washed with isopropanol and then with ether. Five hundred grams of the adduct is mixed with 119.5 g of potassium cyanide, 292 ml of 85% hydrazine hydrate and 910 ml of water. The mixture is stirred overnight at room temperature after which the product is isolated by filtration. The product is washed 3 times with 250 ml portions of water and then 3 times with 230 ml portions of ether. It is then air dried and vacuum dried at room temperature.
Fifty cubic centimeters of concentrated hydrochloric acid is saturated with hydrogen chloride gas at -10°C. To the solution is then added 2.5 g of the intermediate product, of the formula shown above, slowly with vigorous stirring. The mixture is allowed to stir overnight while warming at room temperature gradually. It is then concentrated in vacuo to a syrup. To the residual syrup is added 100 ml of 48% hydrobromic acid. The reaction vessel is purged with nitrogen and the reaction mixture is then refluxed for 3 hours after which it is concentrated in vacuo to a mixture of a syrup and a solid. The residue is taken up in sufficient water to form a clear solution. Activated charcoal is added and the mixture is heated to boiling and filtered.
The filtrate is concentrated to dryness in vacuo and the residue is taken up in 25 cc of ethanol. The residual ammonium bromide is removed by filtration and to the filtrate there is added sufficient diethylamine to change the pH to 6.4. The mixture is warmed to 60°C and then cooled to room temperature. It is then allowed to stand overnight to effect complete crystallization. It is then cooled to 0°C and the product is isolated by filtration, washed with methanol and air dried. The product (α-hydrazino-α-methyl-β-(3,4-dihydroxyphenyl)- propionic acid) is recrystallized once from water using a proportion of 15 cc water per gram of product.

brand name

Lodosyn (Bristol-Myers Squibb).

Therapeutic Function

Muscle relaxant, Antiparkinsonian

General Description

Carbidopa is used for treating restless legs (RL) syndrome and periodic leg movements in sleep (PLMS). Carbidopa along with levodopa is used to treat Parkinson′s disease.

Biological Activity

Peripheral decarboxylase inhibitor, used in combination with levodopa for treatment of Parkinsonism.

Biochem/physiol Actions

Peripheral inhibitor of L-aromatic amino acid decarboxylase. When co-administered with L-DOPA, it prevents extra-CNS conversion to dopamine, thereby increasing CNS concentrations of effective compounds. Selectively cytotoxic to human pulmonary carcinoid and small cell lung carcinoma cells by increasing H2O2 in these cell lines, which are sensitive to reactive oxygen species.

storage

Store at RT

S-(-)-Carbidopa Preparation Products And Raw materials

Raw materials

4-Vinylphenol Sodium bisulfite water solution Diethylamine Sodium bisulfite 4-Hydroxyphenylacetone Butylamine Sodium cyanide Vanillin Nitroethane

Preparation Products

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S-(-)-Carbidopa Suppliers

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View Lastest Price from S-(-)-Carbidopa manufacturers

Baoji Guokang Bio-Technology Co., Ltd.
Product
S-(-)-Carbidopa 28860-95-9
Price
US $1080.00/Kg/Bag
Min. Order
1KG
Purity
99
Supply Ability
100kg
Release date
2021-06-04
henan kanbei chemical co.,ltd
Product
S-(-)-Carbidopa 28860-95-9
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000kg
Release date
2022-09-22
Zhuozhou Wenxi import and Export Co., Ltd
Product
S-(-)-Carbidopa 28860-95-9
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10

28860-95-9, S-(-)-CarbidopaRelated Search:

Basic Violet 1 Methyl acrylate Methylparaben 3-(4-Hydroxyphenyl)propionic acid Acetonitrile Methyltriphenylphosphonium bromide Paraquat dichloride Methyl acetate Methanol Kresoxim-methyl Trimethylphenylammonium chloride Propionic acid Dichloromethylphenylsilane 2,2-Bis(hydroxymethyl)propionic acid 1,5-Diphenylcarbazide Carbidopa Monohydrate L(+)-Lactic acid Methyl

  • mk486
  • 4-dihydroxy-alpha-methyl-alpha-hydrazino-(s)-benzenepropanoicaci
  • 4-dihydroxy-alpha-methyl-alpha-hydrazino-l-hydrocinnamicaci
  • alpha-methyldopahydrazine
  • -Hydrazino-3,4-dihydroxy-methylbenzenep-ropanicacid
  • -Hydrazino-3,4-dihydroxy-methylhy-drocinnamicacid
  • hydrazino-alpha-methyldopa
  • l-alpha-methyldopahydrazine
  • n-aminomethyldopa
  • 3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methyl-propanoic acid
  • (+)-2-(3,4-dihydroxybenzyl)-2-hydrazinopropionic acid monohydrate
  • KINSON
  • CARBIDOPA EDMF
  • [-]-L-α-Hydrazino-3,4-dihydroxy-α-methylhydrocinnamic acid monohydrate
  • s-(-)-α-hydrazino-3,4-dihydroxy-2-methylbenzenepropanoic acid
  • CARBIDOPAANHYDROUS
  • S-(-)-CARBIDOPA,ANHYDROUS
  • S-(-)-ALPHA-HYDRAZINO-3,4-DIHYDROXY-2-METHYLBENZENEPROPANOIC ACID
  • S(-)-ALPHA-HYDRAZINO-3,4-DIHYDROXY-ALPHA-METHYLBENZENEPROPANOIC ACID
  • S-ALPHA-HYDRAZINO-3,4-DIHYDROXY-ALPHA-METHYLBENZENEPROPANOIC ACID
  • (S)-ALPHA-HYDRAZINO-ALPHA-METHYL-BETA-(3,4-DIHYDROXYPHENYL)PROPIONIC ACID
  • (S)-CARBIDOPA
  • S(-)-CARBIDOPA
  • Hydrazino-a-methyldopa
  • L-3-(3,4-Dihydroxyphenyl)-2-methyl-2-hydrazinopropionic acid
  • L-a-Hydrazino-a-methyl-b-(3,4-dihydroxyphenyl)propionic acid
  • S-(-)-a-Hydrazino-3,4-dihydroxy-2-methylbenzenepropanoic acid
  • S(-)-CARBIDOPA >98% L-AROMATIC AMINO ACI D
  • CarbidopaUsp28/Ep5
  • (S)-α-Hydrazino-3,4-dihydroxy-α-methylbenzenepropanoic acid
  • (αS)-3,4-Dihydroxy-α-hydrazino-α-methylhydrocinnamic acid
  • (S)-α-Hydrazino-α-methyl-β-(3,4-dihydroxyphenyl)propionicacid
  • (-)-L-α-Hydrazino-3,4-dihydroxy-α-MethylhydrocinaMic Acid
  • 1-α-(3,4-Dihydroxybenzyl)-α-hydrazinopropionic Acid
  • L-3-(3,4
  • (S)-(-)-Carbidopa-d3 H2O
  • Carbidopa-d3
  • Benzenepropanoic acid, a-hydrazinyl-3,4-dihydroxy-a-Methyl-, (aS)-
  • (αS)-α-hydrazinyl-3,4-dihydroxy-α-methyl-benzenepropanoic acid
  • (S)-3-(3,4-Dihydroxyphenyl)-2-hydrazino-2-methylpropanoic acid
  • Benzenepropanoic acid, α-hydrazinyl-3,4-dihydroxy-α-methyl-, (αS)-
  • (S)-3-(3,4-Dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid
  • S-(-)-CARBIDOPA-D3 (RING)
  • CarbidopaQ: What is Carbidopa Q: What is the CAS Number of Carbidopa Q: What is the storage condition of Carbidopa Q: What are the applications of Carbidopa
  • 28860-95-9
  • C10H14N2O4
  • CC10H14N2O4
  • Aromatic L-amino acid decarboxylase inhibitor
  • A to C
  • BioChemical
  • Biochemicals and Reagents
  • Enzymes, Inhibitors, and Substrates
  • Enzyme Inhibitors
  • Enzyme Inhibitors by Enzyme
  • API
  • Lodosyn
  • L-Aromatic Amino Acid Decarboxylase