L-DOPA

l-DOPA
	Skeletal formula of L-DOPA
	Ball-and-stick model of the zwitterionic form of L-DOPA found in the crystal structure
Clinical data
Pronunciation	/ˌɛlˈdoʊpə/, /ˌlɛvoʊˈdoʊpə/
Trade names	Larodopa, Dopar, Inbrija, others
AHFS/Drugs.com	Professional Drug Facts
MedlinePlus	a619018
License data	EU EMA: by INN; US DailyMed: Levodopa;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth, intravenous
ATC code	N04BA01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only (some forms are OTC); EU: Rx-only;
Pharmacokinetic data
Bioavailability	30%
Metabolism	Aromatic-l-amino-acid decarboxylase
Elimination half-life	0.75–1.5 hours
Excretion	renal 70–80%
Identifiers
	IUPAC name (S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid;
CAS Number	59-92-7 ;
PubChem CID	6047;
IUPHAR/BPS	3639;
DrugBank	DB01235 ;
ChemSpider	5824 ;
UNII	46627O600J;
KEGG	D00059 ;
ChEBI	CHEBI:15765 ;
ChEMBL	ChEMBL1009 ;
CompTox Dashboard (EPA)	DTXSID9023209 ;
ECHA InfoCard	100.000.405
Chemical and physical data
Formula	C9H11NO4
Molar mass	197.190 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@@H](N)Cc1cc(O)c(O)cc1;
	InChI 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 ; Key:WTDRDQBEARUVNC-LURJTMIESA-N ;
	(verify)

l-DOPA, also known as levodopa and l-3,4-dihydroxyphenylalanine, 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] In some plant families (of the order Caryophyllales), l-DOPA is the central precursor of a biosynthetic pathway that produces a class of pigments called betalains.^[6] 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.^[7]

^ Howard ST, Hursthouse MB, Lehmann CW, Poyner EA (1995). "Experimental and theoretical determination of electronic properties in Ldopa". Acta Crystallogr. B. 51 (3): 328–337. Bibcode:1995AcCrB..51..328H. doi:10.1107/S0108768194011407. S2CID 96802274.
^ ^a ^b "Levodopa Use During Pregnancy". Drugs.com. 12 July 2019. Retrieved 27 September 2020.
^ Cite error: The named reference JAMANeuro was invoked but never defined (see the help page).
^ 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.
^ Hiroshima Y, Miyamoto H, Nakamura F, Masukawa D, Yamamoto T, Muraoka H, et al. (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.
^ Polturak G, Breitel D, Grossman N, Sarrion-Perdigones A, Weithorn E, Pliner M, et al. (2016). "Elucidation of the first committed step in betalain biosynthesis enables the heterologous engineering of betalain pigments in plants". New Phytol. 210 (1): 269–283. doi:10.1111/nph.13796. PMID 26683006.
^ 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.

[1] Howard ST, Hursthouse MB, Lehmann CW, Poyner EA (1995). "Experimental and theoretical determination of electronic properties in Ldopa". Acta Crystallogr. B. 51 (3): 328–337. Bibcode:1995AcCrB..51..328H. doi:10.1107/S0108768194011407. S2CID 96802274.

[Drugs.com_pregnancy-2] "Levodopa Use During Pregnancy". Drugs.com. 12 July 2019. Retrieved 27 September 2020.

[JAMANeuro-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, et al. (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] Polturak G, Breitel D, Grossman N, Sarrion-Perdigones A, Weithorn E, Pliner M, et al. (2016). "Elucidation of the first committed step in betalain biosynthesis enables the heterologous engineering of betalain pigments in plants". New Phytol. 210 (1): 269–283. doi:10.1111/nph.13796. PMID 26683006.

[7] 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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