CAS 59-92-7|Levodopa
Introduction：Basic information about CAS 59-92-7|Levodopa, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Levodopa | ||
|---|---|---|---|
| CAS Number | 59-92-7 | Molecular Weight | 197.188 |
| Density | 1.5±0.1 g/cm3 | Boiling Point | 448.4±45.0 °C at 760 mmHg |
| Molecular Formula | C9H11NO4 | Melting Point | 276-278 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | 225.0±28.7 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | L-dopa |
|---|---|
| Synonym | More Synonyms |
Levodopa BiologicalActivity
| Description | L-DOPA is a natural form of DOPA used in the treatment of Parkinson's disease. L-DOPA is the precursor of dopamine and product of tyrosine hydroxylase.Target: Dopamine ReceptorL-DOPA (L-3,4-dihydroxyphenylalanine) is a chemical that is made and used as part of the normal biology of humans, some animals and plants. Some animals and humans make it via biosynthesis from the amino acid L-tyrosine. L-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine collectively known as catecholamines. L-DOPA can be manufactured and in its pure form is sold as apsychoactive drug with the INN levodopa; trade names include Sinemet, Parcopa, Atamet, Stalevo, Madopar, Prolopa, etc. As a drug it is used in the clinical treatment of Parkinson's disease and dopamine-responsive dystonia.L-DOPA crosses the protective blood-brain barrier, whereas dopamine itself cannot. Thus, L-DOPA is used to increase dopamine concentrations in the treatment of Parkinson's disease and dopamine-responsive dystonia. This treatment was made practical and proven clinically by George Cotzias and his coworkers, for which they won the 1969 Lasker Prize. In addition, L-DOPA, co-administered with a peripheral DDCI, has been investigated as a potential treatment for restless leg syndrome. However, studieshave demonstrated "no clear picture of reduced symptoms". |
|---|---|
| Related Catalog | Signaling Pathways >>GPCR/G Protein >>Dopamine ReceptorSignaling Pathways >>Neuronal Signaling >>Dopamine ReceptorNatural Products >>AlkaloidResearch Areas >>Neurological Disease |
| Target | Human Endogenous Metabolite |
| References | [1]. Hyland K, et al. Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. [2]. Merims D, et al. Dopamine dysregulation syndrome, addiction and behavioral changes in Parkinson's disease. Parkinsonism Relat Disord. 2008;14(4):273-80. Epub 2007 Nov 7. |
Chemical & Physical Properties
| Density | 1.5±0.1 g/cm3 |
|---|---|
| Boiling Point | 448.4±45.0 °C at 760 mmHg |
| Melting Point | 276-278 °C(lit.) |
| Molecular Formula | C9H11NO4 |
| Molecular Weight | 197.188 |
| Flash Point | 225.0±28.7 °C |
| Exact Mass | 197.068802 |
| PSA | 103.78000 |
| LogP | -0.22 |
| Vapour Pressure | 0.0±1.1 mmHg at 25°C |
| Index of Refraction | 1.655 |
| InChIKey | WTDRDQBEARUVNC-LURJTMIESA-N |
| SMILES | NC(Cc1ccc(O)c(O)c1)C(=O)O |
| Storage condition | 2-8°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 320 mg/kg/4D-I
- TOXIC EFFECTS :
- Behavioral - excitement Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - nausea or vomiting
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human
- DOSE/DURATION :
- 156 gm/kg/10Y
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Behavioral - hallucinations, distorted perceptions Behavioral - toxic psychosis
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human
- DOSE/DURATION :
- 13 gm/kg/1Y
- TOXIC EFFECTS :
- Behavioral - changes in motor activity (specific assay) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 1780 mg/kg
- TOXIC EFFECTS :
- Behavioral - excitement Behavioral - ataxia Behavioral - aggression
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 624 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - excitement Skin and Appendages - hair
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 2 gm/kg
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold Gastrointestinal - changes in structure or function of salivary glands Lungs, Thorax, or Respiration - other changes
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >100 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 2363 mg/kg
- TOXIC EFFECTS :
- Behavioral - excitement
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 588 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - lacrimation Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 4449 mg/kg
- TOXIC EFFECTS :
- Peripheral Nerve and Sensation - local anesthetic Behavioral - convulsions or effect on seizure threshold Gastrointestinal - changes in structure or function of salivary glands
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 450 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 3500 mg/kg
- TOXIC EFFECTS :
- Autonomic Nervous System - sympathomimetic
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 609 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Bird - wild bird species
- DOSE/DURATION :
- 100 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 70 gm/kg/5W-I
- TOXIC EFFECTS :
- Liver - fatty liver degeneration Liver - changes in liver weight Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 146 gm/kg/26W-I
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 2250 mg/kg/9D-I
- TOXIC EFFECTS :
- Behavioral - changes in motor activity (specific assay) Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 87520 mg/kg/1.5Y-C
- TOXIC EFFECTS :
- Tumorigenic - Carcinogenic by RTECS criteria Skin and Appendages - tumors
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 500 mg/kg
- SEX/DURATION :
- female 1-5 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 22 gm/kg
- SEX/DURATION :
- female 1-22 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 3600 mg/kg
- SEX/DURATION :
- female 9-14 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 6600 mg/kg
- SEX/DURATION :
- female 7-17 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 700 mg/kg
- SEX/DURATION :
- female 1-7 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 480 mg/kg
- SEX/DURATION :
- female 9-14 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 4500 mg/kg
- SEX/DURATION :
- male 15 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- DOSE :
- 5 mg/kg
- SEX/DURATION :
- female 1 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Maternal Effects - ovaries, fallopian tubes
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 4800 mg/kg
- SEX/DURATION :
- female 7-12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetal death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 900 mg/kg
- SEX/DURATION :
- female 7-12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - physical
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 5 gm/kg
- SEX/DURATION :
- female 6-15 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - other measures of fertility
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 2400 mg/kg
- SEX/DURATION :
- female 7-12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 1200 mg/kg
- SEX/DURATION :
- female 7-12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 600 mg/kg
- SEX/DURATION :
- female 7-12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 1200 mg/kg
- SEX/DURATION :
- female 7-12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 2250 mg/kg
- SEX/DURATION :
- female 7-15 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
MUTATION DATA - TYPE OF TEST :
- Mutation in mammalian somatic cells
- TEST SYSTEM :
- Rodent - hamster Lung
- DOSE/DURATION :
- 100 umol/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 238,235,1990 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3795 No. of Facilities: 57 (estimated) No. of Industries: 2 No. of Occupations: 9 No. of Employees: 3893 (estimated) No. of Female Employees: 1571 (estimated)
- TYPE OF TEST :
- Mutation in mammalian somatic cells
- TEST SYSTEM :
- Rodent - hamster Lung
- DOSE/DURATION :
- 100 umol/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 238,235,1990 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3795 No. of Facilities: 57 (estimated) No. of Industries: 2 No. of Occupations: 9 No. of Employees: 3893 (estimated) No. of Female Employees: 1571 (estimated)
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302-H315-H319-H335 |
| Precautionary Statements | P301 + P312 + P330-P305 + P351 + P338 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xn |
| Risk Phrases | R22:Harmful if swallowed. R36/37/38:Irritating to eyes, respiratory system and skin . R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . |
| Safety Phrases | S26-S36-S24/25 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | AY5600000 |
| HS Code | 2932999099 |
Customs
| HS Code | 2922509090 |
|---|---|
| Summary | 2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0% |
Articles252
More Articles| Insights from reconstitution reactions of COPII vesicle formation using pure components and low mechanical perturbation. Biol. Chem. 395(7-8) , 801-12, (2014) As shape transformations of membranes are vital for intracellular trafficking, it is crucial to understand both the mechanics and the biochemistry of these processes. The interplay of these two factor... | |
| Activation of PPAR gamma receptors reduces levodopa-induced dyskinesias in 6-OHDA-lesioned rats. Neurobiol. Dis. 74 , 295-304, (2015) Long-term administration of l-3,4-dihydroxyphenylalanine (levodopa), the mainstay treatment for Parkinson's disease (PD), is accompanied by fluctuations in its duration of action and motor complicatio... | |
| Brexpiprazole I: in vitro and in vivo characterization of a novel serotonin-dopamine activity modulator. J. Pharmacol. Exp. Ther. 350(3) , 589-604, (2014) Brexpiprazole (OPC-34712, 7-{4-[4-(1-benzothiophen-4-yl)piperazin-1-yl]butoxy}quinolin-2(1H)-one) is a novel drug candidate in clinical development for psychiatric disorders with high affinity for ser... |
Synonyms
| (-)-dopa |
| L-3,4-Dihydroxyphenylalanine |
| l-dop |
| Dopar |
| Alanine, 3- (3,4-dihydroxyphenyl)-, L- |
| 3,4-Dihydroxy-L-phenylalanine |
| Doprin |
| L-4,5-Dihydroxyphenylalanine |
| Parda |
| Doparl |
| Tyrosine, 3-hydroxy- |
| Beldopa |
| EINECS 200-445-2 |
| 3-Hydroxytyrosine |
| Levopa |
| Bendopa |
| (−)-dopa |
| L-DOPA |
| MFCD00002598 |
| L-3-(3,4-dihydroxyphenyl)-Alanine |
| Levodopa |
| Ledopa |
