Record Information
Version1.0
Creation date2015-10-09 22:29:11 UTC
Update date2017-01-19 02:36:16 UTC
FoodComEx IDPC000202
FoodDB RecordFDB022678
Chemical Information
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. [HMDB]
CAS Number1199-18-4
Structure
Thumb
Synonyms
SynonymSource
2,4,5-trihydroxyphenethylaminehmdb
5-(2-aminoethyl)-1,2,4-benzenetriolhmdb
6-hydroxy-Dopaminehmdb
6-Hydroxydopaminehmdb
6-OHDAChEBI
HydroxydopamineChEBI
OxidopaminaChEBI
OxidopamineChEBI
OxidopaminumChEBI
Topaminehmdb
Chemical FormulaC8H11NO3
IUPAC name5-(2-aminoethyl)benzene-1,2,4-triol
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
Isomeric SMILESNCCC1=C(O)C=C(O)C(O)=C1
Average Molecular Weight169.1778
Monoisotopic Molecular Weight169.073893223
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 10 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available