HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
3-Hydroxy-D-tyrosin
Levodopa Impurity D · 3,4-DIHYDROXY-D-PHENYLALANINE · (R)-2-AMino-3-(3,4-dihydroxyphenyl)propanoic acid · D-DOPA · Dextrodopa · D-DOPA USP/EP/BP · 3-Hydroxytyrosine · D-3-HYDROXYTYROSINE
Identifikatoren & physikalische Daten
| CAS No. | 5796-17-8 |
|---|---|
| Summenformel | C9H11NO4 |
| Durchschnittliche Molmasse | 197,19 g/mol |
| Monoisotopische Masse | 197,06880783 g/mol |
| SMILES | NC(Cc1ccc(O)c(O)c1)C(=O)O |
| InChIKey | WTDRDQBEARUVNC-UHFFFAOYSA-N |
| PubChem CID | 836 |
| ChEMBL | CHEMBL351042 |
| ChEBI | CHEBI:49168 |
| EC No. | 200-566-0 |
| DTXSID | DTXSID8020549 |
| Lokaler Name | 3-Hydroxy-D-tyrosin |
Chemische & physikalische Eigenschaften
| XLogP | -2,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 104 |
| H-Brücken-Donoren | 4 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 209 |
| Löslichkeit | 3.6 mg/mL0.5 M HCl: soluble |
| Schmelzpunkt | 270 °C276-278 °C(lit.) |
| Physical Description | Solid[Merck Index] White solid[Sigma-Aldrich MSDS] |
| Dissociation Constants | 2.21 |
| Siedepunkt | 448.4±45.0 °C(Predicted) |
| Dichte | 1.468±0.06 g/cm3(Predicted) |
| Lagerbedingungen | -20°C |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 2.24±0.20(Predicted) |
| Farbe | white to tan |
| Merck | 13,3454 |
| BRN | 2417637 |
| Stabilität | Hygroscopic |
| 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-/m1/s1 |
| InChIKey | WTDRDQBEARUVNC-ZCFIWIBFSA-N |
| SMILES | C(O)(=O)[C@@H](CC1=CC=C(O)C(O)=C1)N |
| CAS Datenbank | 5796-17-8(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (16.7%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (91.7%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (91.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (89.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 48 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: DL-Tyrosine, 3-hydroxy- |
| Gefahrenübersicht | A skin and strong eye irritant[Sigma-Aldrich MSDS] See Levodopa. |
| Hazard Classes and Categories | Acute Tox. 4 (16.7%)Skin Irrit. 2 (91.7%)Eye Irrit. 2 (91.7%)STOT SE 3 (89.6%) |
| Treatment | Hospitalization is advised, and general supportive measures should be employed, along with immediate gastric lavage and repeated doses of charcoal over time. This may hasten the elimination of entacapone in particular, by decreasing its absorption/reabsorption from the GI tract. Intravenous fluids should be administered judiciously and an adequate airway maintained. The adequacy of the respiratory, circulatory and renal systems should be carefully monitored and appropriate supportive measures employed. Electrocardiographic monitoring should be instituted and the patient carefully observed for the development of arrhythmiasif required, appropriate antiarrhythmic therapy should be given. The possibility that the patient may have taken other drugs, increasing the risk of drug interactions (especially catechol-structured drugs) should be taken into consideration. Hemodialysis or hemoperfusion is unlikely to reduce entacapone levels due to its high binding to plasma proteins. (L1712)Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. |
| Gesundheitliche Auswirkungen | Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. |
| Expositionspfade | Levodopa is rapidly absorbed from the proximal small intestine by the large neutral amino acid (LNAA) transport carrier system.Endogenous, Ingestion, Dermal (contact) |
| Toxizitätsübersicht | Striatal dopamine levels in symptomatic Parkinson's disease are decreased by 60 to 80%, striatal dopaminergic neurotransmission may be enhanced by exogenous supplementation of dopamine through administration of dopamine's precursor, levodopa. A small percentage of each levodopa dose crosses the blood-brain barrier and is decarboxylated to dopamine. This newly formed dopamine then is available to stimulate dopaminergic receptors, thus compensating for the depleted supply of endogenous dopamine.Uremic toxins such as dihydroxyphenylalanine are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869). |
| Signs and Symptoms | As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Toxicity Data | LD50: 2363 mg/kg (Oral, Mouse) (A308) LD50: 609 mg/kg (Oral, Rabbit) (A308) LD50: 1780 mg/kg (Oral, Rat) (A308) |
| F | 10-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 2922500090 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
D-DOPA (Levodopa EP Impurity D) is a DOPA enantiomer that lacks biological activity.