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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:02 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameDL-Dopa
DescriptionThe 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.
(+/-) 3-(3,4-dihydroxyphenyl)alanineHMDB
2-amino-3-(3,4-Dihydroxyphenyl)propanoic acidHMDB
a-amino-3,4-Dihydroxy-benzenepropanoic acidHMDB
alpha-amino-3,4-Dihydroxy-benzenepropanoic acidHMDB
alpha-amino-Hydrocaffeic acidHMDB
Chemical FormulaC9H11NO4
Average Molecular Weight197.1879
Monoisotopic Molecular Weight197.068807845
IUPAC Name2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
Traditional Name3',4'-dihydroxyphenylalanine
CAS Registry Number63-84-3
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as catecholamines and derivatives. These are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentCatecholamines and derivatives
Alternative Parents
  • 3-phenylpropanoic-acid
  • Catecholamine
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Aralkylamine
  • Amino fatty acid
  • Fatty acyl
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
StatusDetected and Quantified
  • Endogenous
  • Component of Riboflavin metabolism
  • Component of Stilbene, coumarine and lignin biosynthesis
  • Component of Tyrosine metabolism
  • Enzyme co-factor
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
Experimental Properties
Melting Point270 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.6 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility3.3 mg/mLALOGPS
pKa (Strongest Acidic)1.65ChemAxon
pKa (Strongest Basic)9.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.78 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.08 m3·mol-1ChemAxon
Polarizability19.08 Å3ChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0ue9-0900000000-9a2dc91dda37ccd6d764View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-3900000000-51fb8377ac819b0b3100View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00or-9200000000-467c6d2d6b1c5185bac8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uea-0900000000-7cd68d059960262e024cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-31563ea2d36808cf260cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-8900000000-07fa521201594d25db7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-079ea72e0cb84251b6c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0092-1900000000-6bcbd38a361ba2abf5bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9800000000-6e59379b40a21e5e2a33View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-4900000000-51469f201a754d9d871dView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BloodDetected and Quantified14.0 +/- 2.5 uMAdult (>18 years old)BothProgressive dementia details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [17031479 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022140
KNApSAcK IDNot Available
Chemspider ID813
KEGG Compound IDC00355
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00609
Metagene LinkHMDB00609
METLIN IDNot Available
PubChem Compound836
ChEBI ID49168
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. [12649306 ]
  2. Ichise M, Kim YJ, Ballinger JR, Vines D, Erami SS, Tanaka F, Lang AE: SPECT imaging of pre- and postsynaptic dopaminergic alterations in L-dopa-untreated PD. Neurology. 1999 Apr 12;52(6):1206-14. [10214745 ]
  3. Kesten SR, Heffner TG, Johnson SJ, Pugsley TA, Wright JL, Wise LD: Design, synthesis, and evaluation of chromen-2-ones as potent and selective human dopamine D4 antagonists. J Med Chem. 1999 Sep 9;42(18):3718-25. [10479303 ]
  4. Furukawa Y, Nygaard TG, Gutlich M, Rajput AH, Pifl C, DiStefano L, Chang LJ, Price K, Shimadzu M, Hornykiewicz O, Haycock JW, Kish SJ: Striatal biopterin and tyrosine hydroxylase protein reduction in dopa-responsive dystonia. Neurology. 1999 Sep 22;53(5):1032-41. [10496263 ]
  5. Preising M, Op de Laak JP, Lorenz B: Deletion in the OA1 gene in a family with congenital X linked nystagmus. Br J Ophthalmol. 2001 Sep;85(9):1098-103. [11520764 ]
  6. Yoshida M, Hirotsu S, Nakahara M, Uchiwa H, Tomita Y: Histamine is involved in ultraviolet B-induced pigmentation of guinea pig skin. J Invest Dermatol. 2002 Feb;118(2):255-60. [11841541 ]
  7. Ito K, Nagano-Saito A, Kato T, Arahata Y, Nakamura A, Kawasumi Y, Hatano K, Abe Y, Yamada T, Kachi T, Brooks DJ: Striatal and extrastriatal dysfunction in Parkinson's disease with dementia: a 6-[18F]fluoro-L-dopa PET study. Brain. 2002 Jun;125(Pt 6):1358-65. [12023324 ]
  8. Bohme TM, Augelli-Szafran CE, Hallak H, Pugsley T, Serpa K, Schwarz RD: Synthesis and pharmacology of benzoxazines as highly selective antagonists at M(4) muscarinic receptors. J Med Chem. 2002 Jul 4;45(14):3094-102. [12086495 ]
  9. Misu Y, Kitahama K, Goshima Y: L-3,4-Dihydroxyphenylalanine as a neurotransmitter candidate in the central nervous system. Pharmacol Ther. 2003 Feb;97(2):117-37. [12559386 ]
  10. Moore RY, Whone AL, McGowan S, Brooks DJ: Monoamine neuron innervation of the normal human brain: an 18F-DOPA PET study. Brain Res. 2003 Aug 29;982(2):137-45. [12915249 ]
  11. Scherfler C, Khan NL, Pavese N, Eunson L, Graham E, Lees AJ, Quinn NP, Wood NW, Brooks DJ, Piccini PP: Striatal and cortical pre- and postsynaptic dopaminergic dysfunction in sporadic parkin-linked parkinsonism. Brain. 2004 Jun;127(Pt 6):1332-42. Epub 2004 Apr 16. [15090472 ]
  12. Moore RT, Chae KA, Rhodes AR: Laugier and Hunziker pigmentation: a lentiginous proliferation of melanocytes. J Am Acad Dermatol. 2004 May;50(5 Suppl):S70-4. [15097932 ]
  13. Sun M, Kong L, Wang X, Holmes C, Gao Q, Zhang GR, Pfeilschifter J, Goldstein DS, Geller AI: Coexpression of tyrosine hydroxylase, GTP cyclohydrolase I, aromatic amino acid decarboxylase, and vesicular monoamine transporter 2 from a helper virus-free herpes simplex virus type 1 vector supports high-level, long-term biochemical and behavioral correction of a rat model of Parkinson's disease. Hum Gene Ther. 2004 Dec;15(12):1177-96. [15684695 ]
  14. Pahwa R, Lyons KE, Hauser RA: Ropinirole therapy for Parkinson's disease. Expert Rev Neurother. 2004 Jul;4(4):581-8. [15853577 ]
  15. Mann R, Bhathal PS, Bell C: Sympathetic innervation of the liver in man and dog: an immunohistochemical study. Clin Auton Res. 1991 Jun;1(2):141-5. [1688040 ]
  16. Tohgi H, Abe T, Kikuchi T, Takahashi S, Nozaki Y: The significance of 3-O-methyldopa concentrations in the cerebrospinal fluid in the pathogenesis of wearing-off phenomenon in Parkinson's disease. Neurosci Lett. 1991 Oct 28;132(1):19-22. [1787913 ]
  17. Shigetomi S, Buu NT, Kuchel O: Dopaminergic abnormalities in borderline essential hypertensive patients. Hypertension. 1991 Jun;17(6 Pt 2):997-1002. [1904403 ]
  18. Gill JR Jr, Grossman E, Goldstein DS: High urinary dopa and low urinary dopamine-to-dopa ratio in salt-sensitive hypertension. Hypertension. 1991 Nov;18(5):614-21. [1937664 ]
  19. Rosen CF, Seki Y, Farinelli W, Stern RS, Fitzpatrick TB, Pathak MA, Gange RW: A comparison of the melanocyte response to narrow band UVA and UVB exposure in vivo. J Invest Dermatol. 1987 Jun;88(6):774-9. [3108414 ]
  20. Boomsma F, van der Hoorn FA, Schalekamp MA: Determination of aromatic-L-amino acid decarboxylase in human plasma. Clin Chim Acta. 1986 Sep 15;159(2):173-83. [3769207 ]
  21. Muskiet FA, Fremouw-Ottevangers DC, van der Meulen J, Wolthers BG, de Vries JA: Determination of some L-3,4-dihydroxyphenylalanine and dopamine metabolites in urine by means of mass fragmentography. Clin Chem. 1978 Jan;24(1):122-7. [73430 ]
  22. Eldrup E, Mogensen P, Jacobsen J, Pakkenberg H, Christensen NJ: CSF and plasma concentrations of free norepinephrine, dopamine, 3,4-dihydroxyphenylacetic acid (DOPAC), 3,4-dihydroxyphenylalanine (DOPA), and epinephrine in Parkinson's disease. Acta Neurol Scand. 1995 Aug;92(2):116-21. [7484057 ]
  23. Ikeda H, Pastuszko A, Ikegaki N, Kennett RH, Wilson DF: 3,4-dihydroxyphenylalanine (dopa) metabolism and retinoic acid induced differentiation in human neuroblastoma. Neurochem Res. 1994 Dec;19(12):1487-94. [7877718 ]
  24. Cumming P, Gjedde A: Compartmental analysis of dopa decarboxylation in living brain from dynamic positron emission tomograms. Synapse. 1998 May;29(1):37-61. [9552174 ]
  25. Kishore A, Nygaard TG, de la Fuente-Fernandez R, Naini AB, Schulzer M, Mak E, Ruth TJ, Calne DB, Snow BJ, Stoessl AJ: Striatal D2 receptors in symptomatic and asymptomatic carriers of dopa-responsive dystonia measured with [11C]-raclopride and positron-emission tomography. Neurology. 1998 Apr;50(4):1028-32. [9566390 ]
  26. Nakazawa K, Sahuc F, Damour O, Collombel C, Nakazawa H: Regulatory effects of heat on normal human melanocyte growth and melanogenesis: comparative study with UVB. J Invest Dermatol. 1998 Jun;110(6):972-7. [9620308 ]


General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in monooxygenase activity
Specific function:
Plays an important role in the physiology of adrenergic neurons.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
Uniprot ID:
Molecular weight: