Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-06-29 00:47:06 UTC |
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NP-MRD ID | NP0000107 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 6-Hydroxydopamine |
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Description | 6-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. |
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Structure | InChI=1S/C8H11NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10-12H,1-2,9H2 |
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Synonyms | Value | Source |
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2,4,5-Trihydroxyphenethylamine | ChEBI | 6-OHDA | ChEBI | Hydroxydopamine | ChEBI | Oxidopamina | ChEBI | Oxidopaminum | ChEBI | Topamine | ChEBI | 5-(2-Aminoethyl)-1,2,4-benzenetriol | HMDB | 6-Hydroxy-dopamine | HMDB | Oxidopamine hydrochloride | HMDB | Oxidopamine hydrobromide | HMDB | 6 Hydroxydopamine | HMDB | Hydrochloride, oxidopamine | HMDB | Hydrobromide, oxidopamine | HMDB | Oxidopamine | HMDB | 6-Hydroxydopamine | ChEBI |
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Chemical Formula | C8H11NO3 |
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Average Mass | 169.1778 Da |
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Monoisotopic Mass | 169.07389 Da |
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IUPAC Name | 5-(2-aminoethyl)benzene-1,2,4-triol |
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Traditional Name | hydroxydopamine |
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CAS Registry Number | 1199-18-4 |
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SMILES | NCCC1=C(O)C=C(O)C(O)=C1 |
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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 |
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InChI Key | DIVDFFZHCJEHGG-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, DMSO, simulated) | V.dorna83 | | | 2021-08-23 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, DMSO, simulated) | v.dorna83@yahoo.com | Not Available | Not Available | 2021-07-21 | View Spectrum |
| Species |
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Species of Origin | |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | Benzenediols |
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Direct Parent | Catecholamines and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 232 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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External Links |
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HMDB ID | HMDB0001537 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB022678 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4463 |
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KEGG Compound ID | Not Available |
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BioCyc ID | CPD-7666 |
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BiGG ID | Not Available |
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Wikipedia Link | Oxidopamine |
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METLIN ID | 6307 |
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PubChem Compound | 4624 |
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PDB ID | Not Available |
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ChEBI ID | 78741 |
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Good Scents ID | Not Available |
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References |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- Nagatsu T, Sawada M: Inflammatory process in Parkinson's disease: role for cytokines. Curr Pharm Des. 2005;11(8):999-1016. [PubMed:15777250 ]
- Freed WJ, Poltorak M, Becker JB: Intracerebral adrenal medulla grafts: a review. Exp Neurol. 1990 Nov;110(2):139-66. [PubMed:1977606 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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