Levodopa L-DOPA

Levodopa structural formula

Structural formula

Business number 01AT
Molecular formula C9H11NO4
Molecular weight 197.19
label

3-hydroxy-L-tyrosine,

3-(3,4-dihydroxyphenyl)-L-alanine,

L-3-(3,5-dihydroxyphenyl)aniline,

3,4-Dihydroxy-L-phenylalanine,

3-(3,4-Dihydroxyphenyl)-L-alanine L-3-Hydroxytyrosine,

Levodopa,

Amino acid drugs

Numbering system

CAS number:59-92-7

MDL number:MFCD00002598

EINECS number:200-445-2

RTECS number:AY5600000

BRN number:2215169

PubChem number:24277914

Physical property data

1. Properties: White flake or needle crystals or crystalline powder. Odorless. Tasteless.

2. Density (g/mL, 25/4℃): Undetermined

3. Relative vapor density (g/mL, air=1): Undetermined

4. Melting point (ºC): 276~278℃ (284~286℃) (decomposition)

5. Boiling point (ºC, normal pressure): Undetermined

6. Boiling point (ºC, 5.2kPa): Undetermined

7. Refractive index: Undetermined

8. Flash point (ºC): Undetermined

9. Specific rotation (º): 276~278℃ (284~286℃) (decomposition)

10. Autoignition point or ignition temperature (ºC): Undetermined

11. Vapor pressure (kPa, 25ºC): Not determined

12. Saturation vapor pressure (kPa, 60ºC): Not determined

13. Heat of combustion (KJ/mol): Not determined Determined

14. Critical temperature (ºC): Undetermined

15. Critical pressure (KPa): Undetermined

16. Oil and water (octanol/water ) Log value of distribution coefficient: Undetermined

17. Explosion upper limit (%, V/V): Undetermined

18. Explosion lower limit (%, V/V): Undetermined Confirm

19. Solubility: It is easily oxidized in the air when humid and becomes darker in color. Easily soluble in dilute hydrochloric acid and formic acid, soluble in water (66mg/40ml), almost insoluble in ethanol, benzene, chloroform and ethyl acetate.

Toxicological data

None yet

Ecological data

Molecular structure data

5. Molecular property data:

1. Molar refractive index: 49.25

2. Molar volume (cm3/mol): 134.2

3. Isotonic specific volume (90.2K): 401.8

4. Surface tension���dyne/cm): 80.2

5. Polarizability (10-24cm3): 19.52

Compute chemical data

1. Reference value for hydrophobic parameter calculation (XlogP): None

2. Number of hydrogen bond donors: 4

3. Number of hydrogen bond acceptors: 5

4. Number of rotatable chemical bonds: 3

5. Number of tautomers: 18

6. Topological molecule polar surface area 104

7. Number of heavy atoms: 14

8. Surface charge: 0

9. Complexity: 209

10. Number of isotope atoms: 0

11. Determine the number of atomic stereocenters: 1

12. Uncertain number of atomic stereocenters: 0

13. Determine the number of chemical bond stereocenters: 0

14. Number of uncertain chemical bond stereocenters: 0

15. Number of covalent bond units: 1

Properties and stability

L-dopa is an intermediate product of catecholamines formed from tyrosine, which is the precursor of dopamine. About 95% of the L-dopa absorbed into the blood is decarboxylated by dopa decarboxylase in peripheral tissues to form catecholamines, which are difficult to pass through the blood-brain barrier and cause many adverse reactions. Only 1% ofL-dopa enters the cerebral circulation and reaches the central nervous system, where it is converted into catecholamines to exert therapeutic effects. It has no significant pharmacological effect on its own, but exerts its therapeutic effect indirectly through catecholamines.

Storage method

This product should be stored in a dry and dark place filled with argon gas.

Synthesis method

1. Amino acids can be extracted from Mucuna sempervirens Hemsl seeds—— Levodopa. The extraction method is as follows: crush the quinoa beans and extract them three times at room temperature with a mixture of 30% ethanol and 0.1% acetic acid, each time for 24 hours. Filter to get the extract. Concentrate the extract under reduced pressure (21.3kPa) to precipitate crystals, let it stand overnight at 0-10°C, filter, and obtain crude levodopa. Dissolve the crude product with 1N hydrochloric acid, add activated carbon to filter, add a small amount of vitamin C to the filtrate and neutralize it to pH 3.5 with 2N ammonia water, and precipitate a large number of crystals. Let stand at 0-10℃ for 4 hours and filter. The filter cake was washed twice with distilled water containing a small amount of vitamin C, and rinsed and dehydrated once with acetone. Dry at 60-70℃ to obtain levodopa. Based on soy flour, the yield is about 2%. Levodopa can also be obtained by oxidation of L-tyrosine. Dissolve tyrosine in formic phosphoric acid, raise the temperature to 40°C and keep it for 12 hours, and dilute it with 20 times of distilled water. The diluted liquid is passed through a strongly acidic styrene-based cation exchange resin to adsorb unreacted tyrosine, and then undergoes post-chilling operations to obtain the finished product.

2.Artificial synthesis

Purpose

1. Used for biochemical research. Substrate of tyrosinase. medicine. 2. Levodopa is currently one of the effective drugs for the treatment of shaking paralysis. It is one of the precursors for the synthesis of norepinephrine, dopamine, etc. in the body and is a catecholamine. Levodopa can enter the brain through the blood-brain barrier and be decarboxylated by doma decarboxylase into dopamine to exert its effects. But the effect is slow and the side effects are serious.

This article is from the Internet, does not represent the position of Toluene diisocyanate reproduced please specify the source.https://www.allhdi.com/archives/41286

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