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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:52 UTC
HMDB IDHMDB0001537
Secondary Accession Numbers
  • HMDB01537
Metabolite Identification
Common Name6-Hydroxydopamine
Description6-Hydroxydopamine is a naturally occurring amine in human urine. 5-Hydroxydopamine concentration in urine of DOPA treated Parkinson's patients was significantly higher than inpatients not treated or normal controls. (PMID 8255370 ). 6-hydroxydopamine has been found to induce the accumulation of unfolded proteins and then activate the unfolded protein response (UPR) in human neuroblastoma SH-SY5Y cells. (PMID 12486162 ). A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.
Structure
Thumb
Synonyms
ValueSource
2,4,5-TrihydroxyphenethylamineChEBI
6-OHDAChEBI
HydroxydopamineChEBI
OxidopaminaChEBI
OxidopaminumChEBI
TopamineChEBI
5-(2-Aminoethyl)-1,2,4-benzenetriolHMDB
6-Hydroxy-dopamineHMDB
Oxidopamine hydrochlorideMeSH
Oxidopamine hydrobromideMeSH
6 HydroxydopamineMeSH
Hydrochloride, oxidopamineMeSH
Hydrobromide, oxidopamineMeSH
Chemical FormulaC8H11NO3
Average Molecular Weight169.1778
Monoisotopic Molecular Weight169.073893223
IUPAC Name5-(2-aminoethyl)benzene-1,2,4-triol
Traditional Namehydroxydopamine
CAS Registry Number1199-18-4
SMILES
NCCC1=C(O)C=C(O)C(O)=C1
InChI Identifier
InChI=1S/C8H11NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10-12H,1-2,9H2
InChI KeyDIVDFFZHCJEHGG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
Direct ParentCatecholamines and derivatives
Alternative Parents
Substituents
  • Catecholamine
  • Hydroxyquinol derivative
  • Phenethylamine
  • 2-arylethylamine
  • Aralkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Polyol
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Cell and elements:

    Cell:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point232 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.08 g/LALOGPS
logP-0.91ALOGPS
logP-0.15ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.85ChemAxon
pKa (Strongest Basic)9.17ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area86.71 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.23 m³·mol⁻¹ChemAxon
Polarizability17.03 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-8900000000-ec968317710bfa0af4b1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-8339000000-c3b7e127f97564a22ec0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uk9-0900000000-c39da540b6c679cdf01dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-f41c773935ebd031beb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0pdr-4900000000-4462df383c91a9168490View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0900000000-d1d46264304355721947View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-1900000000-b2b31af5a8fedb1fe195View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-9400000000-b62782dd6a193e71ac0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-f10baabe2e89652114f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-21109e5bbac363c8a3e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006y-9800000000-a28d8466178b557c9aa7View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Adrenal Medulla
  • Brain
  • Fibroblasts
  • Kidney
  • Liver
  • Nerve Cells
  • Neuron
  • Spleen
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineDetected and Quantified0.14 (0.06-0.2) umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDDBMET00534
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022678
    KNApSAcK IDNot Available
    Chemspider ID4463
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia Link6-Hydroxydopamine
    METLIN ID6307
    PubChem Compound4624
    PDB IDNot Available
    ChEBI ID317612
    References
    Synthesis ReferenceNapolitano, Alessandra; Crescenzi, Orlando; Pezzella, Alessandro; Prota, Giuseppe. Generation of the Neurotoxin 6-Hydroxydopamine by Peroxidase/H2O2 Oxidation of Dopamine. Journal of Medicinal Chemistry (1995), 38(6), 917-22.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Andrew R, Watson DG, Best SA, Midgley JM, Wenlong H, Petty RK: The determination of hydroxydopamines and other trace amines in the urine of parkinsonian patients and normal controls. Neurochem Res. 1993 Nov;18(11):1175-7. [PubMed:8255370 ]
    2. Schulz TC, Noggle SA, Palmarini GM, Weiler DA, Lyons IG, Pensa KA, Meedeniya AC, Davidson BP, Lambert NA, Condie BG: Differentiation of human embryonic stem cells to dopaminergic neurons in serum-free suspension culture. Stem Cells. 2004;22(7):1218-38. [PubMed:15579641 ]
    3. Ebadi M, Leuschen MP, el Refaey H, Hamada FM, Rojas P: The antioxidant properties of zinc and metallothionein. Neurochem Int. 1996 Aug;29(2):159-66. [PubMed:8837045 ]
    4. Rump LC, Schwertfeger E, Schaible U, Fraedrich G, Schollmeyer P: Beta 2-adrenergic receptor and angiotensin II receptor modulation of sympathetic neurotransmission in human atria. Circ Res. 1994 Mar;74(3):434-40. [PubMed:8118951 ]
    5. Nagatsu T, Sawada M: Inflammatory process in Parkinson's disease: role for cytokines. Curr Pharm Des. 2005;11(8):999-1016. [PubMed:15777250 ]
    6. Freed WJ, Poltorak M, Becker JB: Intracerebral adrenal medulla grafts: a review. Exp Neurol. 1990 Nov;110(2):139-66. [PubMed:1977606 ]
    7. Izumi Y, Sawada H, Sakka N, Yamamoto N, Kume T, Katsuki H, Shimohama S, Akaike A: p-Quinone mediates 6-hydroxydopamine-induced dopaminergic neuronal death and ferrous iron accelerates the conversion of p-quinone into melanin extracellularly. J Neurosci Res. 2005 Mar 15;79(6):849-60. [PubMed:15712215 ]
    8. Shiraga H, Pfeiffer RF, Ebadi M: The effects of 6-hydroxydopamine and oxidative stress on the level of brain metallothionein. Neurochem Int. 1993 Dec;23(6):561-6. [PubMed:8281125 ]
    9. Sajadi A, Bensadoun JC, Schneider BL, Lo Bianco C, Aebischer P: Transient striatal delivery of GDNF via encapsulated cells leads to sustained behavioral improvement in a bilateral model of Parkinson disease. Neurobiol Dis. 2006 Apr;22(1):119-29. Epub 2005 Nov 21. [PubMed:16300956 ]
    10. Lindskog S, Ahren B, Dunning BE, Sundler F: Galanin-immunoreactive nerves in the mouse and rat pancreas. Cell Tissue Res. 1991 May;264(2):363-8. [PubMed:1715243 ]
    11. Nagatsu T: Parkinson's disease: changes in apoptosis-related factors suggesting possible gene therapy. J Neural Transm (Vienna). 2002 May;109(5-6):731-45. [PubMed:12111464 ]
    12. Cao S, Gelwix CC, Caldwell KA, Caldwell GA: Torsin-mediated protection from cellular stress in the dopaminergic neurons of Caenorhabditis elegans. J Neurosci. 2005 Apr 13;25(15):3801-12. [PubMed:15829632 ]
    13. Giaime E, Sunyach C, Herrant M, Grosso S, Auberger P, McLean PJ, Checler F, da Costa CA: Caspase-3-derived C-terminal product of synphilin-1 displays antiapoptotic function via modulation of the p53-dependent cell death pathway. J Biol Chem. 2006 Apr 28;281(17):11515-22. Epub 2006 Feb 22. [PubMed:16495229 ]
    14. Madden KS, Rajan S, Bellinger DL, Felten SY, Felten DL: Age-associated alterations in sympathetic neural interactions with the immune system. Dev Comp Immunol. 1997 Nov-Dec;21(6):479-86. [PubMed:9463781 ]
    15. Ryu EJ, Harding HP, Angelastro JM, Vitolo OV, Ron D, Greene LA: Endoplasmic reticulum stress and the unfolded protein response in cellular models of Parkinson's disease. J Neurosci. 2002 Dec 15;22(24):10690-8. [PubMed:12486162 ]