3-Hydroxy-D-tyrosin

DL-Dopa

HCID 836CAS 5796-17-8

Grundinformationen

Standard-SMILES
NC(Cc1ccc(O)c(O)c1)C(=O)O
InChIKey
WTDRDQBEARUVNC-UHFFFAOYSA-N
Summenformel
C9H11NO4
Durchschnittliche Molmasse
197,19 g/mol
Monoisotopische Masse
197,06880783

Namen und Bezeichner

Bevorzugter Name
DL-Dopa
IUPAC
2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
Lokaler Name
3-Hydroxy-D-tyrosin
Englischer Name
D-DOPA
Summenformel
C9H11NO4
Molmasse
197.19

Namen und Synonyme

DL-DOPA63-84-32-Amino-3-(3,4-dihydroxyphenyl)propanoic aciddihydroxyphenylalanineDL-Dioxyphenylalanine3-Hydroxy-DL-tyrosineDL-3,4-Dopa(+-)-DopaDL-beta-(3,4-Dihydroxyphenyl)alanine(+-)-3-(3,4-Dihydroxyphenyl)alanineQI9C343R60NSC-16940
Weitere Namen anzeigen
Levodopa Impurity D3,4-DIHYDROXY-D-PHENYLALANINE(R)-2-AMino-3-(3,4-dihydroxyphenyl)propanoic acidD-DOPADextrodopaD-DOPA USP/EP/BP3-HydroxytyrosineD-3-HYDROXYTYROSINE3-HYDROXY-D-TYROSINEH-D-TYR(3-HYDROXY)-OH
DOPA, DL-ALANINE, 3-(3,4-DIHYDROXYPHENYL)-, DL-DTXSID8020549CHEBI:491683 Hydroxy DL tyrosinebeta HydroxytyrosineRefChem:5899393,4 Dihydroxyphenylalanine

Datenbank-Bezeichner

CAS
5796-17-8、63-84-3
PubChem CID
836
DTXSID
DTXSID8020549
ChEMBL
CHEMBL351042
ChEBI
CHEBI:49168
UNII
QI9C343R60
EC Number
200-566-0
Nikkaji
J128.150J

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-2,7
Polarare Oberfläche (TPSA)
104 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
3
Schwere Atome
14

Experimentelle und physikochemische Eigenschaften

Solubility3.6 mg/mL
Melting Point270 °C
Physical Description · 2 Einträge

Solid; [Merck Index] White solid; [Sigma-Aldrich MSDS]

Solid

Dissociation Constants2.21

Physikochemische Eigenschaften

Schmelzpunkt
276 · 276-278 °C(lit.)
Siedepunkt
448.4 · 448.4±45.0 °C(Predicted)
Dichte
1.468 · 1.468±0.06 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
Löslichkeit
0.5 M · 0.5 M HCl: soluble
Aggregatzustand
powder

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

Warning

H302 (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 exposure; Respiratory 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.

Gefahrenhinweise

Regulatory InformationChemical: DL-Tyrosine, 3-hydroxy-
Hazards SummaryA skin and strong eye irritant; [Sigma-Aldrich MSDS] See Levodopa.
Hazard Classes and CategoriesAcute Tox. 4 (16.7%);Skin Irrit. 2 (91.7%);Eye Irrit. 2 (91.7%);STOT SE 3 (89.6%)

Toxikologische Informationen

Treatment · 2 Einträge

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 arrhythmias; if 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.

Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Exposure Routes · 2 Einträge

Levodopa is rapidly absorbed from the proximal small intestine by the large neutral amino acid (LNAA) transport carrier system.

Endogenous, Ingestion, Dermal (contact)

Toxicity Summary · 2 Einträge

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 · 1 Eintrag

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 · 2 Einträge

No indication of carcinogenicity to humans (not listed by IARC).

No indication of carcinogenicity to humans (not listed by IARC).

Regulatorische Informationen

Regulatory InformationChemical: DL-Tyrosine, 3-hydroxy-

Sicherheitsdaten

F
10-23
wgk
3
hs_code
2922500090
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

95% of an administered oral dose of levodopa is pre-systemically decarboxylated to dopamine by the L-aromatic amino acid decarboxylase (AAAD) enzyme in the stomach, lumen of the intestine, kidney, and liver. Levodopa also may be methoxylated by the hepatic catechol-O-methyltransferase (COMT) enzyme system to 3-O-methyldopa (3-OMD), which cannot be converted to central dopamine. Half Life: 50 to 90 minutes

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

MeSH Pharmacological ClassificationAny drugs that are used for their effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.
Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 4 Einträge

Dopa is an amino acid in the seedlings, pods, and beans of broad beans and velvet beans; [Merck Index]

Use (kg) in Switzerland (2009): >2500;Use (kg; approx.) in Germany (2009): >25000;Use (kg) in USA (2002): 26200;Use (kg) in France (2004): 24996;Consumption (g per capita) in Switzerland (2009): 0.32;Consumption (g per capita; approx.) in Germany (2009): 0.31;Consumption (g per capita) in the USA (2002): 0.093;Consumption (g per capita) in France (2004): 0.41;Excretion rate: 0.5;Calculated removal (%): 75.1

For the treatment of idiopathic Parkinson's disease (Paralysis Agitans), postencephalitic parkinsonism, symptomatic parkinsonism which may follow injury to the nervous system by carbon monoxide intoxication, and manganese intoxication.

Naturally produced by the body (endogenous).

Anwendungen

VerwendenD-DOPA (Levodopa EP Impurity D) is a DOPA enantiomer that lacks biological activity.

Anbieter50 Anbieter

湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: The D-enantiomer of dopa.

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