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Levodopa
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Name

Levodopa

 EINECS 200-445-2
CAS No. 59-92-7 Density 1.468 g/cm3
PSA 103.78000 LogP 0.75250
Solubility Slightly soluble in water, dilute hydrochloric acid and formic acid. Insoluble in ethanol. Melting Point 276-278 °C(lit.)
Formula C9H11NO4 Boiling Point 448.4 °C at 760 mmHg
Molecular Weight 197.191 Flash Point 225 °C
Transport Information N/A Appearance colorless crystalline powder
Safety 26-36-24/25 Risk Codes 36/37/38-20/21/22
Molecular Structure Molecular Structure of 59-92-7 (Levodopa) Hazard Symbols HarmfulXn
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;

Article Data 100

Levodopa Synthetic route

7423-93-0

(S)-2-amino-3-(3-chloro-4-hydroxyphenyl)propanoic acid

59-92-7

levodopa

Conditions
ConditionsYield
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%
68706-13-8

S,S-m-methoxy-p-acetoxy-N-acetylphenylalanine α-phenylethylamide

59-92-7

levodopa

Conditions
ConditionsYield
With hydrogen bromide96%

C17H19NO5

59-92-7

levodopa

Conditions
ConditionsYield
With 10 wt% Pd(OH)2 on carbon; hydrogen In methanol at 45℃; for 7h; Reagent/catalyst; Temperature; Solvent; Green chemistry;87%

(S)-4'-(3,4-dihydroxybenzyl)-9λ4-boraspiro[bicyclo[3.3.1]nonane-9,2'-[1,3,2]oxazaborolidin]-5'-one

59-92-7

levodopa

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; water at 20℃; for 2h;86%
57-60-3

piruvate

120-80-9

benzene-1,2-diol

59-92-7

levodopa

Conditions
ConditionsYield
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.
330455-62-4

(S)-2-Amino-3-(3,4-diacetoxy-phenyl)-propionic acid ethyl ester

59-92-7

levodopa

Conditions
ConditionsYield
With hydrogenchloride In acetone at 90℃; for 20h;60%
60-18-4

L-tyrosine

59-92-7

levodopa

Conditions
ConditionsYield
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;
63-84-3

dopa

A

59-92-7

levodopa

B

5796-17-8

D-Dopa

63-91-2

L-phenylalanine

A

59-92-7

levodopa

B

7423-92-9

o-hydroxyl-phenylalanine

C

587-33-7, 775-06-4, 2180-37-2, 32140-49-1

m-tyrosine

D

60-18-4

L-tyrosine

Conditions
ConditionsYield
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;
60-18-4

L-tyrosine

A

3131-52-0

1H-indole-5,6-diol

B

59-92-7

levodopa

C

18766-67-1

leucodopachromene

D

3571-34-4, 89762-39-0

(2S)-dopachrome

Conditions
ConditionsYield
With water; mushroom tyrosinase Rate constant; phosphat buffer, ph 6.8;

Levodopa Consensus Reports

Reported in EPA TSCA Inventory.

Levodopa Specification

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.
 

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