(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

• ChemBase ID: 1104
• Molecular Formular: C9H11NO4
• Molecular Mass: 197.18794
• Monoisotopic Mass: 197.06880784
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
• IUPAC Traditional name: levodopa; (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
• Brand Name: 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
• Synonyms: 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; 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

Database IDs

• CAS Number: 59-92-7
• EC Number: 200-445-2
• MDL Number: MFCD00002598
• Beilstein Number: 2215169
• Merck Index: 145464
• PubChem SID: 160964567; 24277914; 46508120; 24863554
• PubChem CID: 6047

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.650697
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.7921518
• LogD (pH = 7.4): -1.8012933
• Log P: -1.7921815
• Molar Refractivity: 49.0781 cm^3
• Polarizability: 19.161877 Å^3
• Polar Surface Area: 103.78 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.32
• LOG S: -1.78
• Solubility (Water): 3.30e+00 g/l

PROPERTIES

Physical Property

• Solubility: 5000 mg/L
• Melting Point: 276-278 °C(lit.); 295°C; ca 295°C dec.
• Optical Rotation: [α]20/D -12±1°, c = 1% in 1 M HCl; [α]25/D -11°, c = 1 in 1 M HCl
• Hydrophobicity(logP): -1.8

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C), Desiccate, Protect from light
• RTECS: AY5600000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; 22-36/37/38; R:22
• Safety Statements: 26-36; 36; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301; H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P264-P270-P301+P310-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: 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)
• Mechanism of Action: Able to cross the blood-brain-barrier; Decarboxylated into dopamine in the basal ganglia and in the periphery markedly increasing serum dopamine; Dopaminergic

Product Information

• Purity: ≥98% (TLC); ≥99.0% (NT); 98+%; 99%
• Salt Data: Free Base
• Optical Purity: ee: 99% (GLC)
• Biological Source: 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.
• Application(s): Antiparkinsonian
• Linear Formula: (HO)2C6H3CH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 05214607

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02101578

Purity: 99%
Crystalline
Used in treatment of Parkinsonism. Also an inhibitor of tyrosine aminotransferase.

DrugBank - DB01235

• 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

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

Biochem/physiol Actions
Natural isomer of the immediate precursor of dopamine; product of tyrosine hydroxylase
Packaging
5, 25, 100, 500 g in poly bottle

Sigma Aldrich - 37830

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

REFERENCES

• http://en.wikipedia.org/wiki/Levodopa
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• Griffith, T. et al., Phytochemistry, 1973, 12, 1651, (biosynth)
• Mostad, A. et al., Acta Chem. Scand., Ser. B, 1974, 28, 1161, (cryst struct)
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• 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