D-DOPA

d-DOPA (d-3,4-dihydroxyphenylalanine; dextrodopa) is similar to l-DOPA (levodopa), but with opposite chirality. Levo- and dextro- rotation refer to a molecule's ability to rotate planes of polarized light in one or the other direction. Whereas l-DOPA is moderately effective in the treatment of Parkinson's disease (PD) and dopamine-responsive dystonia (DRD) by stimulating the production of dopamine in the brain, d-DOPA is biologically inactive.

d-DOPA
Names
IUPAC name
(2R)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.024.858
PubChem CID
UNII
InChI
  • InChI=1/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m1/s1
    Key: WTDRDQBEARUVNC-ZCFIWIBFBC
SMILES
  • O=C(O)[C@H](N)Cc1cc(O)c(O)cc1
Properties
Chemical formula
 C9H11NO4
Molar mass 197.19 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also
  • l-DOPA (Levodopa; Sinemet, Parcopa, Atamet, Stalevo, Madopar, Prolopa, etc.)
  • l-DOPS (Droxidopa)
  • Methyldopa (Aldomet, Apo-Methyldopa, Dopamet, Novomedopa, etc.)
  • Dopamine (Intropan, Inovan, Revivan, Rivimine, Dopastat, Dynatra, etc.)
  • Norepinephrine (Noradrenaline; Levophed, etc.)
  • Epinephrine (Adrenaline; Adrenalin, EpiPen, Twinject, etc.)

References


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