6-Hydroxydopa

6-Hydroxydopa

Clinical data
Other names	6-OH-DOPA; 6-OHDOPA
Drug class	Catecholaminergic neurotoxin
Identifiers
IUPAC name (2S)-2-amino-3-(2,4,5-trihydroxyphenyl)propanoic acid
CAS Number	27244-64-0
PubChem CID	33755
ChemSpider	31117
UNII	580PK2O48O
ChEBI	CHEBI:72753
ChEMBL	ChEMBL1256516
Chemical and physical data
Formula	C9H11NO5
Molar mass	213.189 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=C(C(=CC(=C1O)O)O)C[C@@H](C(=O)O)N
InChI InChI=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 Key: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). ^{[1] [2] [3]} The drug is a derivative of levodopa (L-DOPA). ^{[1] [2] [3]} 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. ^{[1] [2] [3]} 6-OH-DOPA was first described in the scientific literature by 1969. ^[4]

References

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