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59-92-7 分子结构
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(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

ChemBase编号:1104
分子式:C9H11NO4
平均质量:197.18794
单一同位素质量:197.06880784
SMILES和InChIs

SMILES:
Oc1cc(C[C@H](N)C(=O)O)ccc1O
Canonical SMILES:
OC(=O)[C@H](Cc1ccc(c(c1)O)O)N
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
InChIKey:
WTDRDQBEARUVNC-LURJTMIESA-N

引用这个纪录

CBID:1104 http://www.chembase.cn/molecule-1104.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
IUPAC传统名
levodopa
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
商标名
Bendopa
Brocadopa
Cidandopa
Deadopa
Dopaflex
Dopaidan
Dopal
Dopal-Fher
Dopalina
Dopar
Doparkine
Doparl
Dopasol
Dopaston
Dopastral
Doprin
Eldopal
Eldopar
Eldopatec
Eurodopa
Helfo-Dopa
Insulamina
Laradopa
Larodopa
Ledopa
Levedopa
Levopa
Maipedopa
Parda
Pardopa
Prodopa
Veldopa
Weldopa
Syndopa
别名
3,4-二羟基-L-苯丙氨酸
3-(3,4-二羟基苯基)-L-丙氨酸
3-羟基-L-酪氨酸
左多巴
左旋多巴
3-Hydroxy-L-tyrosine
L-Dihydroxyphenylalanine
L-DOPA
DOPA
3,4-dihydroxyphenylalanine
Levodopa
3-(3,4-Dihydroxyphenyl)-L-alanine
L-3-Hydroxytyrosine
Levodopa
L-β-3,4-DIHYDROXYPHENYLALANINE
L-DOPA
Parcopa
Atamet
Stalevo
Madopar
L-Dopa, L-3-Hydroxytyrosine
L-3,4-DIHYDROXYPHENYLALANINE
3,4-Dihydroxy-L-phenylalanine
Bendopa
Brocadopa
Dopar
Larodopa
Levopa
Veldopa
Levodopa
CAS号
59-92-7
EC号
200-445-2
MDL号
MFCD00002598
Beilstein号
2215169
默克索引号
145464
PubChem SID
160964567
24277914
46508120
24863554
PubChem CID
6047

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 1.650697  质子受体
质子供体 LogD (pH = 5.5) -1.7921518 
LogD (pH = 7.4) -1.8012933  Log P -1.7921815 
摩尔折射率 49.0781 cm3 极化性 19.161877 Å3
极化表面积 103.78 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -2.32  LOG S -1.78 
溶解度 3.30e+00 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
5000 mg/L expand 查看数据来源
熔点
276-278 °C(lit.) expand 查看数据来源
295°C expand 查看数据来源
ca 295°C dec. expand 查看数据来源
比旋光度
[α]20/D -12±1°, c = 1% in 1 M HCl expand 查看数据来源
[α]25/D -11°, c = 1 in 1 M HCl expand 查看数据来源
疏水性(logP)
-1.8 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Room Temperature (15-30°C), Desiccate, Protect from light expand 查看数据来源
RTECS编号
AY5600000 expand 查看数据来源
欧盟危险性物质标志
X expand 查看数据来源
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
22 expand 查看数据来源
22-36/37/38 expand 查看数据来源
R:22 expand 查看数据来源
安全公开号
26-36 expand 查看数据来源
36 expand 查看数据来源
S:36/37/39 expand 查看数据来源
TSCA收录
expand 查看数据来源
GHS危险品标识
GHS06 expand 查看数据来源
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H301 expand 查看数据来源
H302-H315-H319-H335 expand 查看数据来源
GHS警示性声明
P261-P305 + P351 + P338 expand 查看数据来源
P264-P270-P301+P310-P321-P405-P501A expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves expand 查看数据来源
相关基因信息
human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)mouse ... DRD1(13488), DRD2(13489), DRD3(13490), DRD4(13491), DRD5(13492)rat ... DRD1(24316), DRD2(24318), DRD3(29238), DRD4(25432), DRD5(25195) expand 查看数据来源
生物活性机理
Able to cross the blood-brain-barrier expand 查看数据来源
Decarboxylated into dopamine in the basal ganglia and in the periphery markedly increasing serum dopamine expand 查看数据来源
Dopaminergic expand 查看数据来源
纯度
≥98% (TLC) expand 查看数据来源
≥99.0% (NT) expand 查看数据来源
98+% expand 查看数据来源
99% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
光学纯度
ee: 99% (GLC) expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
生物来源
Occurs in seedlings and pods of Vicia faba , in Mucuna pruriens, Sarothamnus scoparius, Stizolobium deeringianum, Stizolobium hassjoo, Aristolochia clematitis and other plants. Also prod. by Bacillus spp. expand 查看数据来源
应用领域
Antiparkinsonian expand 查看数据来源
线性分子式
(HO)2C6H3CH2CH(NH2)CO2H expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
MP Biomedicals -  05214607 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals -  02101578 external link
Purity: 99%
Crystalline
Used in treatment of Parkinsonism. Also an inhibitor of tyrosine aminotransferase.
DrugBank -  DB01235 external link
Item Information
Drug Groups approved
Description The naturally occurring form of dihydroxyphenylalanine and the immediate precursor of dopamine. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to dopamine. It is used for the treatment of parkinsonian disorders and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system. [PubChem]
Indication 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.
Pharmacology Levodopa (L-dopa) is used to replace dopamine lost in Parkinson's disease because dopamine itself cannot cross the blood-brain barrier where its precursor can. However, L-DOPA is converted to dopamine in the periphery as well as in the CNS, so it is administered with a peripheral DDC (dopamine decarboxylase) inhibitor such as carbidopa, without which 90% is metabolised in the gut wall, and with a COMT inhibitor if possible; this prevents about a 5% loss. The form given therapeutically is therefore a prodrug which avoids decarboxylation in the stomach and periphery, can cross the blood-brain barrier, and once in the brain is converted to the neurotransmitter dopamine by the enzyme aromatic-L-amino-acid decarboxylase.
Toxicity Oral, mouse: LD50 = 2363 mg/kg; Oral, rabbit: LD50 = 609 mg/kg; Oral, rat: LD50 = 1780 mg/kg.
Affected Organisms
Humans and other mammals
Biotransformation 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.
Absorption Levodopa is rapidly absorbed from the proximal small intestine by the large neutral amino acid (LNAA) transport carrier system.
Half Life 50 to 90 minutes
Protein Binding High
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1726 external link
Research Area: Neurological Disease
Biological Activity:
Levodopa (Sinemet) is an amino acid precursor of dopamine with antiparkinsonian properties. Dopamine is converted from levodopa (Sinemet) by DOPA decarboxylase and can cross the blood-brain barrier. When in the brain, levodopa is decarboxylated to dopamine and stimulates the dopaminergic receptors, thereby compensating for the depleted supply of endogenous dopamine seen in Parkinson’s disease. [1][2]
Sigma Aldrich -  D9628 external link
Biochem/physiol Actions
Natural isomer of the immediate precursor of dopamine; product of tyrosine hydroxylase
包装
5, 25, 100, 500 g in poly bottle
Sigma Aldrich -  37830 external link
Other Notes
Substrate for the assay of tyrosinase (EC 1.14.18.1)1,2; aromatic L-amino acid decarboxylase EC 4.1.1.28)3; lactoperoxidase (EC 1.11.1.7)4

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • http://en.wikipedia.org/wiki/Levodopa
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  • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1190A; 1190B, (nmr)
  • Chapman, R.F. et al., J.C.S.(C), 1970, 865, (dimer)
  • Vorbruggen, H. et al., Chem. Ber., 1972, 105, 1168, (synth)
  • Griffith, T. et al., Phytochemistry, 1973, 12, 1651, (biosynth)
  • Mostad, A. et al., Acta Chem. Scand., Ser. B, 1974, 28, 1161, (cryst struct)
  • Renth, E.-O., Angew. Chem., Int. Ed., 1975, 14, 361, (synth)
  • Fellman, J.H. et al., Biochim. Biophys. Acta, 1975, 381, 9, (isol, deriv)
  • Bartholini, G. et al., Pharmacol. Ther., Part B, 1975, 1, 407, (rev, pharmacol)
  • Gomez, R. et al., Anal. Profiles Drug Subst., 1976, 5, 189, (rev)
  • Dardenne, G. et al., Phytochemistry, 1977, 16, 1822, (deriv)
  • Yamamoto, H. et al., Polymer, 1977, 18, 979; 1978, 19, 1115, (polym)
  • Fuller, W.D. et al., Biopolymers, 1978, 17, 2939, (polym)
  • Danishevsky, S. et al., Tetrahedron, 1981, 37, 4081, (synth)
  • Nutt, J.G. et al., Clin. Neuropharmacol., 1984, 7, 35, (rev, metab)
  • Laycock, M.V. et al., J. Nat. Prod., 1984, 47, 1033, (isol, sulfate)
  • Lee, M. et al., Chem. Pharm. Bull., 1987, 35, 235, (hplc, bibl, anal)
  • Behrman, E.J. et al., Org. Prep. Proced. Int., 1989, 21, 351, (synth, sulfate)
  • Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 1471, (synonyms)
  • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DNA200
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