6-Hydroxydopamine (CHEM021669)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:09:35 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021669
Identification
Common Name6-Hydroxydopamine
ClassSmall Molecule
DescriptionA benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,4,5-TrihydroxyphenethylamineChEBI
6-OHDAChEBI
HydroxydopamineChEBI
OxidopaminaChEBI
OxidopaminumChEBI
TopamineChEBI
5-(2-Aminoethyl)-1,2,4-benzenetriolHMDB
6-Hydroxy-dopamineHMDB
Oxidopamine hydrochlorideMeSH, HMDB
Oxidopamine hydrobromideMeSH, HMDB
6 HydroxydopamineMeSH, HMDB
Hydrochloride, oxidopamineMeSH, HMDB
Hydrobromide, oxidopamineMeSH, HMDB
6-HydroxydopamineChEBI
OxidopamineMeSH
Chemical FormulaC8H11NO3
Average Molecular Mass169.178 g/mol
Monoisotopic Mass169.074 g/mol
CAS Registry Number1199-18-4
IUPAC Name5-(2-aminoethyl)benzene-1,2,4-triol
Traditional Namehydroxydopamine
SMILESNCCC1=C(O)C=C(O)C(O)=C1
InChI IdentifierInChI=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
Description belongs to the class of organic compounds known as catecholamines and derivatives. Catecholamines and derivatives 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
ClassPhenols
Sub ClassBenzenediols
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-8900000000-ec968317710bfa0af4b1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-8339000000-c3b7e127f97564a22ec0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uk9-0900000000-c39da540b6c679cdf01dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-f41c773935ebd031beb2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0pdr-4900000000-4462df383c91a9168490Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-1170-9100000000-7e17c8846c48da0e6c28Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-067de2aeac12b5d386d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0pdr-9800000000-93edb759b0db1c672272Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0900000000-d1d46264304355721947Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-1900000000-b2b31af5a8fedb1fe195Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-9400000000-b62782dd6a193e71ac0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-f10baabe2e89652114f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-21109e5bbac363c8a3e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006y-9800000000-a28d8466178b557c9aa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0900000000-aae03a8148760ccfb8d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-1900000000-69cce15bb35d7f9b2ecfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0q30-9100000000-3ab71c99e27d9e425c1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-e3d8bfd20fe113d52f6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-98fc147d84fd76661021Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9700000000-74dbc04020f90c44cd02Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001537
FooDB IDFDB022678
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-7666
METLIN ID6307
PDB IDNot Available
Wikipedia LinkOxidopamine
Chemspider ID4463
ChEBI ID78741
PubChem Compound ID4624
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12486162
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22789904
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23358137
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23670213
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23959789
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24277157
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24333330
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24885281
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=8255370
10. Napolitano, 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.
11. Napolitano, 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.
12. 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.
13. 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.
14. 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.
15. Nagatsu T, Sawada M: Inflammatory process in Parkinson's disease: role for cytokines. Curr Pharm Des. 2005;11(8):999-1016.
16. Freed WJ, Poltorak M, Becker JB: Intracerebral adrenal medulla grafts: a review. Exp Neurol. 1990 Nov;110(2):139-66.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. 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.
25. 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.
26. 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.