ContaminantDB: L-Dopa

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (8)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:42 UTC

Update Date

2026-05-14 16:58:57 UTC

Accession Number

CHEM002382

Identification

Common Name

L-Dopa

Class

Small Molecule

Description

L-Dopa is used for the treatment of Parkinsonian disorders and Dopa-Responsive Dystonia and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system. Peripheral tissue conversion may be the mechanism of the adverse effects of levodopa. It is standard clinical practice to co-administer a peripheral DOPA decarboxylase inhibitor - carbidopa or benserazide - and often a catechol-O-methyl transferase (COMT) inhibitor, to prevent synthesis of dopamine in peripheral tissue. 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] L-Dopa is the naturally occurring form of dihydroxyphenylalanine and the immediate precursor of dopamine. Unlike dopamine itself, L-Dopa can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to dopamine. In particular, it is metabolized to dopamine by aromatic L-amino acid decarboxylase. Pyridoxal phosphate (vitamin B6) is a required cofactor for this decarboxylation, and may be administered along with levodopa, usually as pyridoxine.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
Suspected Compounds - Waste Water
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Antidyskinetic
Antiparkinson Agent
Dopamine Agent
Drug
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(-)-3-(3,4-Dihydroxyphenyl)-L-alanine	ChEBI
(-)-Dopa	ChEBI
3,4-Dihydroxy-L-phenylalanine	ChEBI
3,4-DIHYDROXYPHENYLALANINE	ChEBI
3-Hydroxy-L-tyrosine	ChEBI
beta-(3,4-Dihydroxyphenyl)-L-alanine	ChEBI
beta-(3,4-Dihydroxyphenyl)alanine	ChEBI
Dihydroxy-L-phenylalanine	ChEBI
Dopar	ChEBI
L-beta-(3,4-Dihydroxyphenyl)alanine	ChEBI
Levodopa	ChEBI
Levodopum	ChEBI
b-(3,4-Dihydroxyphenyl)-L-alanine	Generator
Β-(3,4-dihydroxyphenyl)-L-alanine	Generator
b-(3,4-Dihydroxyphenyl)alanine	Generator
Β-(3,4-dihydroxyphenyl)alanine	Generator
L-b-(3,4-Dihydroxyphenyl)alanine	Generator
L-Β-(3,4-dihydroxyphenyl)alanine	Generator
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoate	HMDB
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid	HMDB
3,4-Dihydroxyphenyl-L-alanine	HMDB
3-(3,4-Dihydroxyphenyl)-L-alanine	HMDB
b-(3,4-Dihydroxyphenyl)-a-L-alanine	HMDB
Bendopa	HMDB
beta-(3,4-Dihydroxyphenyl)-alpha-L-alanine	HMDB
Cidandopa	HMDB
Dihydroxyphenylalanine	HMDB
Dopaflex	HMDB
Dopaidan	HMDB
Dopal	HMDB
Dopalina	HMDB
Doparkine	HMDB
Doparl	HMDB
Dopasol	HMDB
Dopaston	HMDB
Dopastone	HMDB
Dopastral	HMDB
Dopicar	HMDB
Doprin	HMDB
Eldopal	HMDB
Eldopar	HMDB
Eldopatec	HMDB
Eurodopa	HMDB
Helfo-dopa	HMDB
Insulamina	HMDB
L-(-)-Dopa	HMDB
L-3-(3,4-Dihydroxyphenyl)-alanine	HMDB
L-4-5-Dihydroxyphenylalanine	HMDB
L-b-(3,4-Dihydroxyphenyl)-a-alanine	HMDB
L-beta-(3,4-Dihydroxyphenyl)-alpha-alanine	HMDB
L-Dihydroxyphenylalanine	HMDB
Laradopa	HMDB
Larodopa	HMDB
Ledopa	HMDB
Levedopa	HMDB
Levopa	HMDB
Maipedopa	HMDB
Parda	HMDB
Pardopa	HMDB
Prodopa	HMDB
Syndopa	HMDB
Veldopa	HMDB
Weldopa	HMDB
3 Hydroxy L tyrosine	HMDB
Roche brand OF levodopa	HMDB
L 3,4 Dihydroxyphenylalanine	HMDB
L-3,4-Dihydroxyphenylalanine	HMDB
Medphano brand OF levodopa	HMDB
L Dopa	HMDB
Roberts brand OF levodopa	HMDB

Chemical Formula

C₉H₁₁NO₄

Average Molecular Mass

197.188 g/mol

Monoisotopic Mass

197.069 g/mol

CAS Registry Number

59-92-7

IUPAC Name

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

Traditional Name

levodopa

SMILES

N[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O

InChI Identifier

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

InChI Key

WTDRDQBEARUVNC-LURJTMIESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Tyrosine and derivatives

Alternative Parents

Substituents

Tyrosine or derivatives
Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
Catechol
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:15765 )
L-tyrosine derivative (CHEBI:15765 )
dopa (CHEBI:15765 )
Other amino acids (C00355 )
Biogenic amines (C00355 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Adrenal Medulla
Bladder
Brain
Epidermis
Intestine
Muscle
Nerve Cells
Neuron
Placenta
Platelet
Prostate
Striatum

Pathways

Name	SMPDB Link	KEGG Link
Tryptophan Metabolism	SMP00063	map00380
Catecholamine Biosynthesis	SMP00012	map00350
Tyrosine Metabolism	SMP00006	map00350
Aromatic L-Aminoacid Decarboxylase Deficiency	SMP00170	Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	284-285°C
Boiling Point	Not Available
Solubility	5000 mg/L (at 20°C)

Predicted Properties

Property	Value	Source
logP	-1.8	ChemAxon
pKa (Strongest Acidic)	1.65	ChemAxon
pKa (Strongest Basic)	9.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	103.78 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.08 m³·mol⁻¹	ChemAxon
Polarizability	18.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-014i-0790000000-b2f7f063a2c8197c7edd	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014i-0690000000-622497b3104c6082a45d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-00xr-9350000000-b0cc4636931d2de64d81	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-014i-0590000000-4474e81e4226bb4e1d4c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0790000000-b2f7f063a2c8197c7edd	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0690000000-622497b3104c6082a45d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-9350000000-b0cc4636931d2de64d81	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-0590000000-4474e81e4226bb4e1d4c	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1890000000-646d209fa1943582a336	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0690000000-720ed87e98a0d9f1721d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-3900000000-266d9baeda773fe1fb22	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0002-4193000000-8c76bf85d8a897e9403c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0uea-0900000000-8eb71aa0cc8622f097a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a59-2900000000-bf63b9b719959b82b543	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-056r-9300000000-a78b0b31dd33fe8479a7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0f6t-0911000000-15affa616923dfb9c45a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-22d8267801d0eb0b73c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-2c310034a1a871502b4c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-5e6020c952f741531fcb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0007-0970100000-49594dae82ce73e734e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-2183a68f58b951f3f1c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-0900000000-0030db588fbd92c5b761	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-0090000000-544615463a975baae9e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0729111000-0a20b01f58fff8ad7ef0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-c8095a31ed4b3dbbc646	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0190000000-41515cba3a6929721859	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0900000000-8074c509ef5bae1129fc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0502193020-497bfad7ba247159ca00	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-0b0d4b6dcb7f1fa24e1a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0029800000-05f40324c8c1fec7963a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0000090000-c0cd80185ce47b30e5fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0900000000-df116b84981cf4a1371a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0f6t-0900000000-1c1c39a8880442ea18df	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udj-0900000000-cf54b26df05181b0d2fc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-d506f2673b114b8e38d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-8900000000-1699873cb7650f62b5bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-a0d81bfc4868b0d1cbf9	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

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

Mechanism of Toxicity

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.

Metabolism

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

Toxicity Values

LD50: 2363 mg/kg (Oral, Mouse) (1) LD50: 609 mg/kg (Oral, Rabbit) (1) LD50: 1780 mg/kg (Oral, Rat) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

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. (23)

Concentrations

Not Available

External Links

DrugBank ID

DB01235

HMDB ID

HMDB0000181

FooDB ID

FDB000567

Phenol Explorer ID

Not Available

KNApSAcK ID