Editing L-DOPA (section)

{{Short description|Chemical compound}}
{{Merge to|Levodopa|date=April 2025}}
{{About|<small>L</small>-DOPA as a biological compound|its role as a medication and supplement|Levodopa}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{DISPLAYTITLE:<small>L</small>-DOPA}}
{{Use dmy dates|date=September 2024}}

{{Chembox
<!-- Images -->
| ImageFile = 3,4-Dihydroxy-L-phenylalanin (Levodopa).svg
| ImageSize = 
| ImageClass = skin-invert
| ImageCaption = [[Skeletal formula]] of <small>L</small>-DOPA
| ImageFile2 = L-DOPA-from-xtal-view-2-3D-bs-17.png
| ImageSize2 = 180px
| ImageCaption2 = [[Ball-and-stick model]] of the [[zwitterion]]ic form of <small>L</small>-DOPA found in the [[crystal structure]]<ref>{{ cite journal | title = Experimental and theoretical determination of electronic properties in Ldopa | vauthors = Howard ST, Hursthouse MB, Lehmann CW, Poyner EA | journal = [[Acta Crystallographica|Acta Crystallogr. B]] | volume = 51 | pages = 328–337 | year = 1995 | issue = 3 | doi = 10.1107/S0108768194011407 | bibcode = 1995AcCrB..51..328H | s2cid = 96802274 }}</ref>
<!-- Names -->
| IUPACName = (''S'')-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid
| OtherNames = {{sm|l}}-3,4-Dihydroxyphenylalanine; Levodopa
<!-- Sections -->
| Section1 = {{Chembox Identifiers
| CASNo = 59-92-7
| ChEBI = 15765
| ChEMBL = 1009
| ChemSpiderID = 5824
| DrugBank = DB01235
| EINECS = 200-445-2
| EC_number = 
| 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
| InChIKey = WTDRDQBEARUVNC-LURJTMIESA-N
| KEGG = C00355
| MeSHName = 
| PubChem = 6047
| SMILES = C1=CC(=C(C=C1C[C@@H](C(=O)O)N)O)O
| UNII = 46627O600J
  }}
| Section2 = {{Chembox Properties
| C=9 | H=11 | N=1 | O=4
| MolarMass = 197.19 g/mol
| Appearance = 
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility = 
  }}
| Section3 = {{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = 
  }}
}}

'''{{sm|l}}-DOPA''', also known as '''{{sm|l}}-3,4-dihydroxyphenylalanine''' and used medically as '''levodopa''', is made and used as part of the normal [[biology]] of some plants<ref name="JAMANeuro">{{cite journal | vauthors = Cohen PA, Avula B, Katragunta K, Khan I | title = Levodopa Content of Mucuna pruriens Supplements in the NIH Dietary Supplement Label Database | journal = JAMA Neurology | volume = 79 | issue = 10 | pages = 1085–1086 | date = October 2022 | pmid = 35939305 | doi = 10.1001/jamaneurol.2022.2184 | pmc = 9361182 }}</ref> and animals, including humans. Humans, as well as a portion of the other animals that utilize {{sm|l}}-DOPA, make it via [[biosynthesis]] from the [[amino acid]] [[L-tyrosine|{{sm|l}}-tyrosine]].

{{sm|l}}-DOPA is the [[precursor (chemistry)|precursor]] to the [[neurotransmitter]]s [[dopamine]], [[norepinephrine]] (noradrenaline), and [[epinephrine]] (adrenaline), which are collectively known as [[catecholamine]]s. Furthermore, {{sm|l}}-DOPA itself mediates [[Neurotrophic factors|neurotrophic factor]] release by the brain and [[central nervous system]].<ref>{{cite journal | vauthors = Lopez VM, Decatur CL, Stamer WD, Lynch RM, McKay BS | title = L-DOPA is an endogenous ligand for OA1 | journal = PLOS Biology | volume = 6 | issue = 9 | pages = e236 | date = September 2008 | pmid = 18828673 | pmc = 2553842 | doi = 10.1371/journal.pbio.0060236 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Hiroshima Y, Miyamoto H, Nakamura F, Masukawa D, Yamamoto T, Muraoka H, Kamiya M, Yamashita N, Suzuki T, Matsuzaki S, Endo I, Goshima Y | title = The protein Ocular albinism 1 is the orphan GPCR GPR143 and mediates depressor and bradycardic responses to DOPA in the nucleus tractus solitarii | journal = British Journal of Pharmacology | volume = 171 | issue = 2 | pages = 403–14 | date = January 2014 | pmid = 24117106 | pmc = 3904260 | doi = 10.1111/bph.12459 }}</ref> In some plant families (of the order [[Caryophyllales]]), {{sm|l}}-DOPA is the central precursor of a biosynthetic pathway that produces a class of pigments called [[betalain]]s.<ref>{{cite journal |vauthors= Polturak G, Breitel D, Grossman N, Sarrion-Perdigones A, Weithorn E, Pliner M, Orzaez D, Granell A, Rogachev I, Aharoni A |title=Elucidation of the first committed step in betalain biosynthesis enables the heterologous engineering of betalain pigments in plants |journal= New Phytol |volume=210 |issue=1 |pages= 269–283 |year=2016 |doi=10.1111/nph.13796 |doi-access=free |pmid=26683006 |bibcode=2016NewPh.210..269P }}</ref>

{{sm|l}}-DOPA can be manufactured and in its pure form is sold as a [[drug]] with the {{Abbrlink|INN|International Nonproprietary Name}} ''[[levodopa]]''. As a drug, it is used in the [[therapy|treatment]] of [[Parkinson's disease]] and [[dopamine-responsive dystonia]], as well as [[restless leg syndrome]].<ref>{{cite journal |last1=Scholz |first1=Hanna |last2=Trenkwalder |first2=Claudia |last3=Kohnen |first3=Ralf |last4=Kriston |first4=Levente |last5=Riemann |first5=Dieter |last6=Hornyak |first6=Magdolna |title=Levodopa for the treatment of restless legs syndrome |journal=Cochrane Database of Systematic Reviews |date=15 February 2011 |volume=2011 |issue=5 |pages=CD005504 |doi=10.1002/14651858.CD005504.pub2 |pmid=21328278 |s2cid=196338172 |pmc=8889887 }}</ref>

{{sm|l}}-DOPA has a counterpart with opposite [[chirality (chemistry)#By configuration: D- and L-|chirality]], [[D-DOPA|{{sm|d}}-DOPA]]. As is true for many molecules, the human body produces only one of these [[isomer]]s (the {{sm|l}}-DOPA form). The [[Enantiomer|enantiomeric purity]] of {{sm|l}}-DOPA may be analyzed by determination of the optical rotation or by chiral [[thin-layer chromatography]].<ref>{{cite journal | vauthors = Martens J, Günther K, Schickedanz M | title = Resolution of Optical Isomers by Thin-Layer Chromatography: Enantiomeric Purity of Methyldopa | journal = [[Arch. Pharm.]] | volume = 319 | issue = 6 | pages = 572–574 | date = 1986 | doi = 10.1002/ardp.19863190618 | s2cid = 97903386 }}</ref>