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| CAS No.: | 59-92-7 |
|---|---|
| Name: | Levodopa |
| Molecular Structure: | |
|
|
|
| Formula: | C9H11NO4 |
| Molecular Weight: | 197.191 |
| Synonyms: | Syndopa;(-)-3-(3,4-Dihydroxyphenyl)-L-alanine;L-(o-Dihydroxyphenyl)alanine;Bendopa;Dopaston;Dopar (TN);Deadopa;Prodopa;.Beta.-(3,4-Dihydroxyphenyl)-L-alanine;Brocadopa;3-Hydroxy-L-tyrosine;Dopasol;3, 4-Dihydroxy-L-phenylalanine;Pardopa;Maipedopa;L-3,4-Dihydrophenylalanine;3-(3,4-Dithydroxyphenyl)-L-alanine;Dopal-Fher;L-o-Hydroxytyrosine;Component of Sinemet;Larodopa;Alanine, 3-(3, 4-dihydroxyphenyl)-, (-)-;Dopaflex;Levopa;L-dopa;L-.Beta.-(3,4-Dihydroxyphenyl)alanine;3,4-Dihydroxy-L-phenylalanine;Insulamina;L(-)-Dopa;Eldopal;L-Tyrosine,3-hydroxy-;Eldopar;Alanine, 3-(3,4-dihydroxyphenyl)-;Dopaston SE;Helfo-Dopa;Dopalina;L-DOPA LEVODOPA; |
| EINECS: | 200-445-2 |
| Density: | 1.468 g/cm3 |
| Melting Point: | 276-278 °C(lit.) |
| Boiling Point: | 448.4 °C at 760 mmHg |
| Flash Point: | 225 °C |
| Solubility: | Slightly soluble in water, dilute hydrochloric acid and formic acid. Insoluble in ethanol. |
| Appearance: | colorless crystalline powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 36/37/38-20/21/22 |
| Safety: | 26-36-24/25 |
| PSA: | 103.78000 |
| LogP: | 0.75250 |
| Conditions | Yield |
|---|---|
| Stage #1: (S)-2-amino-3-(3-chloro-4-hydroxyphenyl)propanoic acid With sodium nitrate; 2-Methylcyclohexanol; N-bromoacetamide at 56℃; for 2.16667h; Stage #2: With nickel dichloride at 25℃; for 4h; Temperature; | 98.7% |
S,S-m-methoxy-p-acetoxy-N-acetylphenylalanine α-phenylethylamide
levodopa
| Conditions | Yield |
|---|---|
| With hydrogen bromide | 96% |
levodopa
| Conditions | Yield |
|---|---|
| With 10 wt% Pd(OH)2 on carbon; hydrogen In methanol at 45℃; for 7h; Reagent/catalyst; Temperature; Solvent; Green chemistry; | 87% |
levodopa
| Conditions | Yield |
|---|---|
| With tetrabutyl ammonium fluoride In tetrahydrofuran; water at 20℃; for 2h; | 86% |
| Conditions | Yield |
|---|---|
| With ethylenediaminetetraacetic acid; pyridoxal 5'-phosphate; Ammonium; recombinant wild-type thermophilic tyrosine phenol lyases from thermophilic microorganism Symbiobacterium toebii In aq. phosphate buffer at 37℃; pH=8; Catalytic behavior; Green chemistry; Enzymatic reaction; stereoselective reaction; | 65% |
| With ammonium acetate at 45℃; β-tyrosinase from Symbiobacterium thermophilum, 0.4 mM pyridoxal phosphate, 8 mM EDTA, 0.1 percent dithiothreitol; | 90 % Turnov. |
(S)-2-Amino-3-(3,4-diacetoxy-phenyl)-propionic acid ethyl ester
levodopa
| Conditions | Yield |
|---|---|
| With hydrogenchloride In acetone at 90℃; for 20h; | 60% |
| Conditions | Yield |
|---|---|
| With phosphate buffer at 37℃; Irradiation; also with m-tyrosine; | |
| With dihydroxyfumaric acid; acetate buffer; oxygen; horse radish peroxidase at 0℃; for 3h; Product distribution; other aromatic compounds, different peroxidases; | |
| With air; mushroom monophenol monooxygenase In water at 23℃; for 0.15h; Rate constant; pH 6.6; |
L-phenylalanine
A
levodopa
B
o-hydroxyl-phenylalanine
C
m-tyrosine
D
L-tyrosine
| Conditions | Yield |
|---|---|
| With oxygen; Fe(2+)-EDTA In water at 40℃; for 4h; electrochemical cell, pH 3; | |
| With oxygen; Fe(2+)-EDTA In water at 40℃; for 4h; Product distribution; electrochem. oxidation; pH: 3; | |
| With dihydrogen peroxide; ascorbic acid In water at 37℃; Product distribution; hydroxylation with various reaction systems; | |
| With Tris-HCl buffer; 6,7-dimethyl-5,6,7,8-tetrahydropterin; 2-hydroxyethanethiol; catalase; phenylalanine hydroxylase at 37℃; for 0.5h; Product distribution; further enzyme; |
L-tyrosine
A
1H-indole-5,6-diol
B
levodopa
C
leucodopachromene
D
(2S)-dopachrome
| Conditions | Yield |
|---|---|
| With water; mushroom tyrosinase Rate constant; phosphat buffer, ph 6.8; |
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Reported in EPA TSCA Inventory.
1. Introduction of Levodopa
Levodopa, with the IUPAC Name of (2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid, is one kind of colorless crystalline powder. This product belongs to the Product Category which include Pharmaceutical; Amino Acids; Biochemistry; Biological-modified Amino Acids; Nutritional Supplements; Natural Plant Extract. Besides, Levodopa could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
2. Properties of Levodopa
Levodopa has the following datas: (1)Index of Refraction: 1.654; (2)Molar Refractivity: 49.25 cm3; (3)Molar Volume: 134.2 cm3 ; (4)Surface Tension: 80.2 dyne/cm; (5)Density: 1.468 g/cm3; (6)Flash Point: 225 °C; (7)Enthalpy of Vaporization: 74.5 kJ/mol; (8)Boiling Point: 448.4 °C at 760 mmHg; (9)Vapour Pressure: 7.97E-09 mmHg at 25 °C; (10) Melting point: 276-278 °C(lit.); (11)Storage tempreture: 2-8 °C.
3. Structure Descriptors of Levodopa
You could convert the following datas into the molecular structure:
(1).Canonical SMILES: C1=CC(=C(C=C1CC(C(=O)O)N)O)O
(2).Isomeric SMILES: C1=CC(=C(C=C1C[C@@H](C(=O)O)N)O)O
(3).InChI: InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1
(4).InChIKey: WTDRDQBEARUVNC-LURJTMIESA-N
4. Safety information of Levodopa
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-Parkinsonian drug. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: 
Xi
The Risk Statements information of D-glucose :
41: Risk of serious damage to eyes
36/37/38: Irritating to eyes, respiratory system and skin
The Risk Statements information of D-glucose :
22: Do not breathe dust
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
24/25: Avoid contact with skin and eyes
WGK Germany: 1
Hazard Note: Irritant/Light Sensitive
5. Toxicity of Levodopa
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| bird - wild | LD50 | oral | 100mg/kg (100mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
| human | TDLo | oral | 13gm/kg/1Y (13000mg/kg) | BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Journal of Neurology, Neurosurgery and Psychiatry. Vol. 34, Pg. 668, 1971. |
| human | TDLo | oral | 156gm/kg/10Y (156000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TOXIC PSYCHOSIS BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | Journal of Neurology, Neurosurgery and Psychiatry. Vol. 34, Pg. 502, 1971. |
| mouse | LD50 | intraperitoneal | 588mg/kg (588mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE | Toxicology and Applied Pharmacology. Vol. 28, Pg. 1, 1974. |
| mouse | LD50 | intravenous | 450mg/kg (450mg/kg) | Toxicology and Applied Pharmacology. Vol. 28, Pg. 1, 1974. | |
| mouse | LD50 | oral | 2363mg/kg (2363mg/kg) | BEHAVIORAL: EXCITEMENT | Toxicology and Applied Pharmacology. Vol. 28, Pg. 1, 1974. |
| mouse | LD50 | subcutaneous | 4449mg/kg (4449mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS PERIPHERAL NERVE AND SENSATION: LOCAL ANESTHETIC | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 3, Pg. 186, 1972. |
| mouse | LDLo | unreported | 3500mg/kg (3500mg/kg) | AUTONOMIC NERVOUS SYSTEM: SYMPATHOMIMETIC | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 153, Pg. 161, 1930. |
| rabbit | LD50 | oral | 609mg/kg (609mg/kg) | Toxicology and Applied Pharmacology. Vol. 28, Pg. 1, 1974. | |
| rat | LD50 | intraperitoneal | 624mg/kg (624mg/kg) | SKIN AND APPENDAGES (SKIN): HAIR: OTHER BEHAVIORAL: EXCITEMENT SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE | Toxicology and Applied Pharmacology. Vol. 28, Pg. 1, 1974. |
| rat | LD50 | intravenous | > 100mg/kg (100mg/kg) | Drugs in Japan Vol. 6, Pg. 905, 1982. | |
| rat | LD50 | oral | 1780mg/kg (1780mg/kg) | BEHAVIORAL: AGGRESSION BEHAVIORAL: ATAXIA BEHAVIORAL: EXCITEMENT | Toxicology and Applied Pharmacology. Vol. 28, Pg. 1, 1974. |
| rat | LD50 | subcutaneous | 2gm/kg (2000mg/kg) | GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 3, Pg. 186, 1972. |
| women | TDLo | oral | 320mg/kg/4D-I (320mg/kg) | BEHAVIORAL: EXCITEMENT LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: NAUSEA OR VOMITING | American Heart Journal. Vol. 110, Pg. 488, 1985. |
