基本情報
- 標準SMILES
NC(Cc1ccc(O)c(O)c1)C(=O)O- InChIKey
WTDRDQBEARUVNC-UHFFFAOYSA-N- 分子式
- C9H11NO4
- 平均分子量
- 197.19 g/mol
- 単同位体質量
- 197.06880783
名称と識別子
- 優先名称
- DL-Dopa
- IUPAC
- 2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
- 現地名
- 3-ヒドロキシ-D-チロシン
- 英語名
- D-DOPA
- 分子式
- C9H11NO4
- 分子量
- 197.19
名称と別名
名称をさらに表示
データベース識別子
- 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
物性
構造計算による物性
- XLogP
- -2.7
- 極性表面積
- 104 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 5
- 回転可能結合数
- 3
- 重原子数
- 14
- 形式電荷
- 0
- 複雑度
- 209
実験および物理化学的性質
Physical Description
Solid; [Merck Index] White solid; [Sigma-Aldrich MSDS]
Solid
物理化学的性質
- 融点
- 276 · 276-278 °C(lit.)
- 比旋光度
- 11 · D11 +13.0° (c = 5.27 in 1N HCl)
- 沸点
- 448.4 · 448.4±45.0 °C(Predicted)
- 比重(密度)
- 1.468 · 1.468±0.06 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- 0.5 M · 0.5 M HCl: 可溶
- 外見
- 粉
- 酸解離定数(Pka)
- 2.24 · 2.24±0.20(Predicted)
- 色
- 白から黄褐色
- Merck
- 13 · 13,3454
- BRN
- 2417637 · 2417637
- 安定性
- 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 データベース
- 5796 · 5796-17-8(CAS DataBase Reference)
化学的性質
化学的特性Tan Solid
安全と法規制
GHS分類
GHS Classification
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.
危険有害性情報
毒性情報
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 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.
Exposure Routes
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
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).
No indication of carcinogenicity to humans (not listed by IARC).
法規制情報
安全データ
- F
- 10-23
- wgk
- 3
- hs_code
- 2922500090
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Metabolism/Metabolites
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.
用途と製造
Uses
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).
応用分野
使用D-DOPA (Levodopa EP Impurity D) is a DOPA enantiomer that lacks biological activity.
調製方法
純化方法Likely impurities are vanillin, hippuric acid, 3-methoxytyrosine and 3-aminotyrosine. DOPA recrystallises from large volumes of H2O forming colourless white needles; its solubility in H2O is 0.165%, but it is insoluble in EtOH, *C6H6, CHCl3, and EtOAc. Also crystallise it by dissolving it in dilute HCl and adding dilute ammonia to give pH 5, under N2. Alternatively, crystallise it from dilute aqueous EtOH. It is rapidly oxidised in air when moist, and darkens, particularly in alkaline solution. Dry it in vacuo at 70o in the dark, and store it in a dark container preferably under N2. It has at 220.5nm (log 3.79) and 280nm (log 3.42) in 0.001N max HCl. [Yamada et al. Chem Pharm Bull Jpn 10 693 1962, Bretschneider et al. Helv Chim Acta 56 2857 1973, NMR: Jardetzky & Jardetzky J Biol Chem 233 383 1958, Beilstein 4 IV 2492, 2493.]
サプライヤー50 社
補足説明
定義ChEBI: The D-enantiomer of dopa.
関連反応
関連ノート
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