6-Hydroxydopa Explained

Class:	Catecholaminergic neurotoxin
Cas Number:	27244-64-0
Pubchem:	33755
Chemspiderid:	31117
Unii:	580PK2O48O
Chebi:	72753
Chembl:	1256516
Synonyms:	6-OH-DOPA; 6-OHDOPA
Iupac Name:	(2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid
C:	9
H:	11
N:	1
O:	5
Smiles:	C1=C(C(=CC(=C1O)O)O)C[C@@H](C(=O)O)N
Stdinchi:	1S/C9H11NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11-13H,1,10H2,(H,14,15)/t5-/m0/s1
Stdinchikey:	YLKRUSPZOTYMAT-YFKPBYRVSA-N

6-Hydroxydopa (6-OH-DOPA; 6-OHDOPA) is a catecholaminergic neurotoxin that damages noradrenergic and dopaminergic neurons and is used in scientific research.^[1] ^[2] ^[3] It is a precursor and prodrug of 6-hydroxydopamine (6-OHDA). The drug is a derivative of levodopa (L-DOPA). It has certain advantages over 6-OHDA, such as the ability to cross the blood–brain barrier into the central nervous system and hence the ability to be administered systemically rather than directly into the brain. 6-OH-DOPA was first described in the scientific literature by 1969.^[4]

Notes and References

Book: Kostrzewa RM . Handbook of Neurotoxicity . Survey of Selective Monoaminergic Neurotoxins Targeting Dopaminergic, Noradrenergic, and Serotoninergic Neurons . Springer International Publishing . Cham . 2022 . 978-3-031-15079-1 . 10.1007/978-3-031-15080-7_53 . 159–198.
Book: Kostrzewa RM . Perinatal Lesioning and Lifelong Effects of the Noradrenergic Neurotoxin 6-Hydroxydopa . 29 . 43–50 . 2016 . 26660536 . 10.1007/7854_2015_414 . 978-3-319-34134-7 . Current Topics in Behavioral Neurosciences .
Kostrzewa RM, Brus R . Destruction of catecholamine-containing neurons by 6-hydroxydopa, an endogenous amine oxidase cofactor . Amino Acids . 14 . 1–3 . 175–179 . 1998 . 9871458 . 10.1007/BF01345259 .
Ong HH, Creveling CR, Daly JW . The synthesis of 2,4,5-trihydroxyphenylalanine (6-hydroxydopa). A centrally active norepinephrine-depleting agent . Journal of Medicinal Chemistry . 12 . 3 . 458–462 . May 1969 . 5788162 . 10.1021/jm00303a028 .