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L-DOPA

l-DOPA
3,4-Dihydroxy-L-phenylalanin (Levodopa).svg
Skeletal formula of L-DOPA
L-DOPA-from-xtal-view-2-3D-bs-17.png
Ball-and-stick model of the zwitterionic form of L-DOPA found in the crystal structure[1]
Clinical data
Pronunciation/ˌɛlˈdoʊpə/, /ˌlɛvoʊˈdoʊpə/
Trade namesLarodopa, Dopar, Inbrija, others
AHFS/Drugs.comProfessional Drug Facts
MedlinePlusa619018
License data
Pregnancy
category
Routes of
administration		By mouth, intravenous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only (some forms are OTC)
  • EU: Rx-only
Pharmacokinetic data
Bioavailability30%
MetabolismAromatic-l-amino-acid decarboxylase
Elimination half-life0.75–1.5 hours
Excretionrenal 70–80%
Identifiers
  • (S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.405 Edit this at Wikidata
Chemical and physical data
FormulaC9H11NO4
Molar mass197.190 g·mol−1
3D model (JSmol)
  • O=C(O)[C@@H](N)Cc1cc(O)c(O)cc1
  • InChI=1S/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-/m0/s1 checkY
  • Key:WTDRDQBEARUVNC-LURJTMIESA-N checkY
  (verify)

l-DOPA, also known as levodopa and l-3,4-dihydroxyphenylalanine, is an amino acid that is made and used as part of the normal biology of some plants [3] and animals, including humans. Humans, as well as a portion of the other animals that utilize l-DOPA, make it via biosynthesis from the amino acid l-tyrosine. l-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), which are collectively known as catecholamines. Furthermore, l-DOPA itself mediates neurotrophic factor release by the brain and CNS.[4][5] l-DOPA can be manufactured and in its pure form is sold as a psychoactive drug with the INN levodopa; trade names include Sinemet, Pharmacopa, Atamet, and Stalevo. As a drug, it is used in the clinical treatment of Parkinson's disease and dopamine-responsive dystonia.

l-DOPA has a counterpart with opposite chirality, d-DOPA. As is true for many molecules, the human body produces only one of these isomers (the l-DOPA form). The enantiomeric purity of l-DOPA may be analyzed by determination of the optical rotation or by chiral thin-layer chromatography.[6]

  1. ^ Howard ST, Hursthouse MB, Lehmann CW, Poyner EA (1995). "Experimental and theoretical determination of electronic properties in Ldopa". Acta Crystallogr. B. 51: 328–337. doi:10.1107/S0108768194011407.
  2. ^ a b "Levodopa Use During Pregnancy". Drugs.com. 12 July 2019. Retrieved 27 September 2020.
  3. ^ Cite error: The named reference JAMANeuro was invoked but never defined (see the help page).
  4. ^ Lopez VM, Decatur CL, Stamer WD, Lynch RM, McKay BS (September 2008). "L-DOPA is an endogenous ligand for OA1". PLOS Biology. 6 (9): e236. doi:10.1371/journal.pbio.0060236. PMC 2553842. PMID 18828673.
  5. ^ Hiroshima Y, Miyamoto H, Nakamura F, Masukawa D, Yamamoto T, Muraoka H, Kamiya M, Yamashita N, Suzuki T, Matsuzaki S, Endo I, Goshima Y (January 2014). "The protein Ocular albinism 1 is the orphan GPCR GPR143 and mediates depressor and bradycardic responses to DOPA in the nucleus tractus solitarii". British Journal of Pharmacology. 171 (2): 403–14. doi:10.1111/bph.12459. PMC 3904260. PMID 24117106.
  6. ^ Martens J, Günther K, Schickedanz M (1986). "Resolution of Optical Isomers by Thin-Layer Chromatography: Enantiomeric Purity of Methyldopa". Arch. Pharm. 319 (6): 572–574. doi:10.1002/ardp.19863190618. S2CID 97903386.
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