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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:46 UTC

HMDB ID

HMDB0001537

Secondary Accession Numbers

HMDB01537

Metabolite Identification

Common Name

6-Hydroxydopamine

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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      18.848 -11.952   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.848 -10.412   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.172 -12.714   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.493 -12.714   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.172  -9.626   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      17.493  -9.626   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      21.519 -11.952   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.170 -11.952   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.519 -10.412   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      22.843 -12.714   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      14.822 -12.714   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      22.843  -9.626   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2                                                            
CONECT    7    3   10    9                                                  
CONECT    8    4   11                                                       
CONECT    9    5    7   12                                                  
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
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	MeSH, HMDB
Oxidopamine hydrobromide	MeSH, HMDB
6 Hydroxydopamine	MeSH, HMDB
Hydrochloride, oxidopamine	MeSH, HMDB
Hydrobromide, oxidopamine	MeSH, HMDB
6-Hydroxydopamine	ChEBI
Oxidopamine	MeSH

Chemical Formula

C₈H₁₁NO₃

Average Molecular Weight

169.1778

Monoisotopic Molecular Weight

169.073893223

IUPAC Name

5-(2-aminoethyl)benzene-1,2,4-triol

Traditional Name

hydroxydopamine

CAS Registry Number

1199-18-4

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 Key

DIVDFFZHCJEHGG-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Catecholamines 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

primary amino compound (CHEBI:78741 )
catecholamine (CHEBI:78741 )
benzenetriol (CHEBI:78741 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0001537)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0001537)

Organ substructure

Adrenal medulla (HMDB: HMDB0001537)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 8255370)

Cellular substructure

Cytoplasm (HMDB: HMDB0001537)

Source

Endogenous

Endogenous (HMDB: HMDB0001537)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Biological role

Drug metabolite (HMDB: HMDB0001537)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	232 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	143.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002189

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.08 g/L	ALOGPS
logP	-0.91	ALOGPS
logP	-0.15	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.85	ChemAxon
pKa (Strongest Basic)	9.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	86.71 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.23 m³·mol⁻¹	ChemAxon
Polarizability	17.03 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	135.611	31661259
DarkChem	[M-H]-	132.706	31661259
AllCCS	[M+H]+	137.537	32859911
AllCCS	[M-H]-	135.068	32859911
DeepCCS	[M+H]+	138.372	30932474
DeepCCS	[M-H]-	134.543	30932474
DeepCCS	[M-2H]-	172.27	30932474
DeepCCS	[M+Na]+	147.809	30932474
AllCCS	[M+H]+	137.5	32859911
AllCCS	[M+H-H2O]+	133.2	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.7	32859911
AllCCS	[M-H]-	135.1	32859911
AllCCS	[M+Na-2H]-	136.2	32859911
AllCCS	[M+HCOO]-	137.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Hydroxydopamine	NCCC1=C(O)C=C(O)C(O)=C1	3124.7	Standard polar	33892256
6-Hydroxydopamine	NCCC1=C(O)C=C(O)C(O)=C1	2225.7	Standard non polar	33892256
6-Hydroxydopamine	NCCC1=C(O)C=C(O)C(O)=C1	1927.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Hydroxydopamine,1TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=C(O)C=C1CCN	1908.7	Semi standard non polar	33892256
6-Hydroxydopamine,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C(CCN)C=C1O	1869.1	Semi standard non polar	33892256
6-Hydroxydopamine,1TMS,isomer #3	C[Si](C)(C)OC1=CC(CCN)=C(O)C=C1O	1873.4	Semi standard non polar	33892256
6-Hydroxydopamine,1TMS,isomer #4	C[Si](C)(C)NCCC1=CC(O)=C(O)C=C1O	2084.8	Semi standard non polar	33892256
6-Hydroxydopamine,2TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C(CCN)C=C1O	1834.9	Semi standard non polar	33892256
6-Hydroxydopamine,2TMS,isomer #2	C[Si](C)(C)OC1=CC(CCN)=C(O[Si](C)(C)C)C=C1O	1846.4	Semi standard non polar	33892256
6-Hydroxydopamine,2TMS,isomer #3	C[Si](C)(C)NCCC1=CC(O)=C(O)C=C1O[Si](C)(C)C	2040.6	Semi standard non polar	33892256
6-Hydroxydopamine,2TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C(CCN)C=C1O[Si](C)(C)C	1840.9	Semi standard non polar	33892256
6-Hydroxydopamine,2TMS,isomer #5	C[Si](C)(C)NCCC1=CC(O)=C(O[Si](C)(C)C)C=C1O	2018.6	Semi standard non polar	33892256
6-Hydroxydopamine,2TMS,isomer #6	C[Si](C)(C)NCCC1=CC(O[Si](C)(C)C)=C(O)C=C1O	2022.6	Semi standard non polar	33892256
6-Hydroxydopamine,2TMS,isomer #7	C[Si](C)(C)N(CCC1=CC(O)=C(O)C=C1O)[Si](C)(C)C	2263.4	Semi standard non polar	33892256
6-Hydroxydopamine,3TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1CCN	1880.6	Semi standard non polar	33892256
6-Hydroxydopamine,3TMS,isomer #2	C[Si](C)(C)NCCC1=CC(O)=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C	1989.0	Semi standard non polar	33892256
6-Hydroxydopamine,3TMS,isomer #3	C[Si](C)(C)NCCC1=CC(O[Si](C)(C)C)=C(O)C=C1O[Si](C)(C)C	1992.5	Semi standard non polar	33892256
6-Hydroxydopamine,3TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C(O)C=C1CCN([Si](C)(C)C)[Si](C)(C)C	2227.9	Semi standard non polar	33892256
6-Hydroxydopamine,3TMS,isomer #5	C[Si](C)(C)NCCC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1O	1999.8	Semi standard non polar	33892256
6-Hydroxydopamine,3TMS,isomer #6	C[Si](C)(C)OC1=CC(O)=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1O	2208.2	Semi standard non polar	33892256
6-Hydroxydopamine,3TMS,isomer #7	C[Si](C)(C)OC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=C(O)C=C1O	2216.6	Semi standard non polar	33892256
6-Hydroxydopamine,4TMS,isomer #1	C[Si](C)(C)NCCC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C	2046.9	Semi standard non polar	33892256
6-Hydroxydopamine,4TMS,isomer #1	C[Si](C)(C)NCCC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C	2080.8	Standard non polar	33892256
6-Hydroxydopamine,4TMS,isomer #1	C[Si](C)(C)NCCC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C	1997.5	Standard polar	33892256
6-Hydroxydopamine,4TMS,isomer #2	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1O	2201.3	Semi standard non polar	33892256
6-Hydroxydopamine,4TMS,isomer #2	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1O	2246.4	Standard non polar	33892256
6-Hydroxydopamine,4TMS,isomer #2	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1O	2139.4	Standard polar	33892256
6-Hydroxydopamine,4TMS,isomer #3	C[Si](C)(C)OC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1O	2199.7	Semi standard non polar	33892256
6-Hydroxydopamine,4TMS,isomer #3	C[Si](C)(C)OC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1O	2241.0	Standard non polar	33892256
6-Hydroxydopamine,4TMS,isomer #3	C[Si](C)(C)OC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1O	2142.2	Standard polar	33892256
6-Hydroxydopamine,4TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	2204.3	Semi standard non polar	33892256
6-Hydroxydopamine,4TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	2239.4	Standard non polar	33892256
6-Hydroxydopamine,4TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	2128.2	Standard polar	33892256
6-Hydroxydopamine,5TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1CCN([Si](C)(C)C)[Si](C)(C)C	2272.6	Semi standard non polar	33892256
6-Hydroxydopamine,5TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1CCN([Si](C)(C)C)[Si](C)(C)C	2188.4	Standard non polar	33892256
6-Hydroxydopamine,5TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1CCN([Si](C)(C)C)[Si](C)(C)C	2018.1	Standard polar	33892256
6-Hydroxydopamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(O)C=C1CCN	2168.0	Semi standard non polar	33892256
6-Hydroxydopamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(CCN)C=C1O	2136.4	Semi standard non polar	33892256
6-Hydroxydopamine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(CCN)=C(O)C=C1O	2133.1	Semi standard non polar	33892256
6-Hydroxydopamine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCC1=CC(O)=C(O)C=C1O	2344.8	Semi standard non polar	33892256
6-Hydroxydopamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C(CCN)C=C1O	2305.6	Semi standard non polar	33892256
6-Hydroxydopamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CCN)=C(O[Si](C)(C)C(C)(C)C)C=C1O	2313.8	Semi standard non polar	33892256
6-Hydroxydopamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCC1=CC(O)=C(O)C=C1O[Si](C)(C)C(C)(C)C	2504.6	Semi standard non polar	33892256
6-Hydroxydopamine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(CCN)C=C1O[Si](C)(C)C(C)(C)C	2309.6	Semi standard non polar	33892256
6-Hydroxydopamine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NCCC1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C1O	2491.7	Semi standard non polar	33892256
6-Hydroxydopamine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NCCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C1O	2499.4	Semi standard non polar	33892256
6-Hydroxydopamine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(CCC1=CC(O)=C(O)C=C1O)[Si](C)(C)C(C)(C)C	2683.0	Semi standard non polar	33892256
6-Hydroxydopamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1CCN	2519.9	Semi standard non polar	33892256
6-Hydroxydopamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2695.7	Semi standard non polar	33892256
6-Hydroxydopamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C1O[Si](C)(C)C(C)(C)C	2699.3	Semi standard non polar	33892256
6-Hydroxydopamine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(O)C=C1CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2867.8	Semi standard non polar	33892256
6-Hydroxydopamine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NCCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O	2721.9	Semi standard non polar	33892256
6-Hydroxydopamine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	2895.5	Semi standard non polar	33892256
6-Hydroxydopamine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(O)C=C1O	2895.6	Semi standard non polar	33892256
6-Hydroxydopamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2927.4	Semi standard non polar	33892256
6-Hydroxydopamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2801.4	Standard non polar	33892256
6-Hydroxydopamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2502.2	Standard polar	33892256
6-Hydroxydopamine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	3114.7	Semi standard non polar	33892256
6-Hydroxydopamine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	2984.5	Standard non polar	33892256
6-Hydroxydopamine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	2552.3	Standard polar	33892256
6-Hydroxydopamine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O	3105.1	Semi standard non polar	33892256
6-Hydroxydopamine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O	2982.2	Standard non polar	33892256
6-Hydroxydopamine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O	2555.6	Standard polar	33892256
6-Hydroxydopamine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3119.3	Semi standard non polar	33892256
6-Hydroxydopamine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2986.1	Standard non polar	33892256
6-Hydroxydopamine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2545.5	Standard polar	33892256
6-Hydroxydopamine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3369.2	Semi standard non polar	33892256
6-Hydroxydopamine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3034.9	Standard non polar	33892256
6-Hydroxydopamine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2561.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxydopamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-8900000000-ec968317710bfa0af4b1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxydopamine GC-MS (3 TMS) - 70eV, Positive	splash10-00di-8339000000-c3b7e127f97564a22ec0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxydopamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxydopamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Hydroxydopamine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0uk9-0900000000-c39da540b6c679cdf01d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Hydroxydopamine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0udi-0900000000-f41c773935ebd031beb2	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Hydroxydopamine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0pdr-4900000000-4462df383c91a9168490	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Hydroxydopamine 40V, Positive-QTOF	splash10-1170-9100000000-7e17c8846c48da0e6c28	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Hydroxydopamine 10V, Positive-QTOF	splash10-0udi-2900000000-067de2aeac12b5d386d7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Hydroxydopamine 20V, Positive-QTOF	splash10-0pdr-9800000000-93edb759b0db1c672272	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxydopamine 10V, Positive-QTOF	splash10-0fk9-0900000000-d1d46264304355721947	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxydopamine 20V, Positive-QTOF	splash10-0uk9-1900000000-b2b31af5a8fedb1fe195	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxydopamine 40V, Positive-QTOF	splash10-014r-9400000000-b62782dd6a193e71ac0a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxydopamine 10V, Negative-QTOF	splash10-014i-0900000000-f10baabe2e89652114f7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxydopamine 20V, Negative-QTOF	splash10-014i-0900000000-21109e5bbac363c8a3e8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxydopamine 40V, Negative-QTOF	splash10-006y-9800000000-a28d8466178b557c9aa7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxydopamine 10V, Positive-QTOF	splash10-0fk9-0900000000-aae03a8148760ccfb8d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxydopamine 20V, Positive-QTOF	splash10-0ufr-1900000000-69cce15bb35d7f9b2ecf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxydopamine 40V, Positive-QTOF	splash10-0q30-9100000000-3ab71c99e27d9e425c1f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxydopamine 10V, Negative-QTOF	splash10-014i-0900000000-e3d8bfd20fe113d52f6a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxydopamine 20V, Negative-QTOF	splash10-014i-0900000000-98fc147d84fd76661021	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxydopamine 40V, Negative-QTOF	splash10-006x-9700000000-74dbc04020f90c44cd02	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Adrenal Medulla
Brain
Fibroblasts
Kidney
Liver
Neuron
Spleen

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	0.14 (0.06-0.2) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	8255370	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022678

KNApSAcK ID

Not Available

Chemspider ID

4463

KEGG Compound ID

Not Available

BioCyc ID

CPD-7666

BiGG ID

Not Available

Wikipedia Link

Oxidopamine

METLIN ID

6307

PubChem Compound

4624

PDB ID

Not Available

ChEBI ID

78741

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

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.

Material Safety Data Sheet (MSDS)

Not Available

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 ]

Showing metabocard for 6-Hydroxydopamine (HMDB0001537)

MOL for HMDB0001537 (6-Hydroxydopamine)

3D MOL for HMDB0001537 (6-Hydroxydopamine)

3D SDF for HMDB0001537 (6-Hydroxydopamine)

3D-SDF for HMDB0001537 (6-Hydroxydopamine)

PDB for HMDB0001537 (6-Hydroxydopamine)

3D PDB for HMDB0001537 (6-Hydroxydopamine)

SMILES for HMDB0001537 (6-Hydroxydopamine)

INCHI for HMDB0001537 (6-Hydroxydopamine)

Structure for HMDB0001537 (6-Hydroxydopamine)

3D Structure for HMDB0001537 (6-Hydroxydopamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra