Np mrd loader

Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:47:06 UTC
NP-MRD IDNP0000107
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-Hydroxydopamine
Description6-Hydroxydopamine, also known as 6-OHDA or oxidopamina, 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. The main use for oxidopamine in scientific research is to induce Parkinsonism in laboratory animals such as mice, rats and monkeys, in order to develop and test new medicines and treatments for Parkinson's disease. In order to induce this condition in animals, around 70% of the dopaminergic neurons in the substantia nigra of the brain must be destroyed, and this is achieved either with oxidopamine or MPTP. 6-OHDA is thought to enter the neurons via the dopamine and noradrenaline (norepinephrine) reuptake transporters. Oxidopamine toxicity in neonatal rodents is also used as an animal model for the Lesch-Nyhan syndrome. Both these agents likely destroy neurons by generating reactive oxygen species such as superoxide radical. Oxidopamine is often used in conjunction with a selective noradrenaline reuptake inhibitor (such as desipramine) to selectively destroy dopaminergic neurons.
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 hydrochlorideHMDB
Oxidopamine hydrobromideHMDB
6 HydroxydopamineHMDB
Hydrochloride, oxidopamineHMDB
Hydrobromide, oxidopamineHMDB
OxidopamineHMDB
6-HydroxydopamineChEBI
Chemical FormulaC8H11NO3
Average Mass169.1778 Da
Monoisotopic Mass169.07389 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)V.dorna832021-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)V.dorna832021-08-23View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, simulated)V.dorna832021-07-21View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001537
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022678
KNApSAcK IDNot Available
Chemspider ID4463
KEGG Compound IDNot Available
BioCyc IDCPD-7666
BiGG IDNot Available
Wikipedia LinkOxidopamine
METLIN ID6307
PubChem Compound4624
PDB IDNot Available
ChEBI ID78741
Good Scents IDNot Available
References
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 ]