Not Available
Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:39:08 UTC
Update Date2024-10-09 19:16:51 UTC
Metabolite IDMMDBc0000498
Metabolite Identification
Common NameL-Dopa
DescriptionL-DOPA, also known as levodopa or 3,4-dihydroxyphenylalanine is an alpha amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). L-DOPA is found naturally in both animals and plants. It is made via biosynthesis from the amino acid L-tyrosine by the enzyme tyrosine hydroxylase.. L-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), which are collectively known as catecholamines. The Swedish scientist Arvid Carlsson first showed in the 1950s that administering L-DOPA to animals with drug-induced (reserpine) Parkinsonian symptoms caused a reduction in the intensity of the animals' symptoms. Unlike dopamine itself, L-DOPA can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to dopamine. In particular, it is metabolized to dopamine by aromatic L-amino acid decarboxylase. Pyridoxal phosphate (vitamin B6) is a required cofactor for this decarboxylation, and may be administered along with levodopa, usually as pyridoxine. As a result, L-DOPA is a drug that is now used for the treatment of Parkinsonian disorders and DOPA-Responsive Dystonia. It is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system. It is standard clinical practice in treating Parkinsonism to co-administer a peripheral DOPA decarboxylase inhibitor - carbidopa or benserazide - and often a catechol-O-methyl transferase (COMT) inhibitor, to prevent synthesis of dopamine in peripheral tissue. Side effects of L-DOPA treatment may include: hypertension, arrhythmias, nausea, gastrointestinal bleeding, disturbed respiration, hair loss, disorientation and confusion. L-DOPA can act as an L-tyrosine mimetic and be incorporated into proteins by mammalian cells in place of L-tyrosine, generating protease-resistant and aggregate-prone proteins in vitro and may contribute to neurotoxicity with chronic L-DOPA administration. L-phenylalanine, L-tyrosine, and L-DOPA are all precursors to the biological pigment melanin. The enzyme tyrosinase catalyzes the oxidation of L-DOPA to the reactive intermediate dopaquinone, which reacts further, eventually leading to melanin oligomers.
Structure
Synonyms
ValueSource
(-)-3-(3,4-Dihydroxyphenyl)-L-alanineChEBI
(-)-DopaChEBI
3,4-Dihydroxy-L-phenylalanineChEBI
3,4-DIHYDROXYPHENYLALANINEChEBI
3-Hydroxy-L-tyrosineChEBI
beta-(3,4-Dihydroxyphenyl)-L-alanineChEBI
beta-(3,4-Dihydroxyphenyl)alanineChEBI
Dihydroxy-L-phenylalanineChEBI
DoparChEBI
L-beta-(3,4-Dihydroxyphenyl)alanineChEBI
LevodopaChEBI
LevodopumChEBI
b-(3,4-Dihydroxyphenyl)-L-alanineGenerator
Β-(3,4-dihydroxyphenyl)-L-alanineGenerator
b-(3,4-Dihydroxyphenyl)alanineGenerator
Β-(3,4-dihydroxyphenyl)alanineGenerator
L-b-(3,4-Dihydroxyphenyl)alanineGenerator
L-Β-(3,4-dihydroxyphenyl)alanineGenerator
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoateHMDB
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acidHMDB
3,4-Dihydroxyphenyl-L-alanineHMDB
3-(3,4-Dihydroxyphenyl)-L-alanineHMDB
b-(3,4-Dihydroxyphenyl)-a-L-alanineHMDB
BendopaHMDB
beta-(3,4-Dihydroxyphenyl)-alpha-L-alanineHMDB
CidandopaHMDB
DihydroxyphenylalanineHMDB
DopaflexHMDB
DopaidanHMDB
DopalHMDB
DopalinaHMDB
DoparkineHMDB
DoparlHMDB
DopasolHMDB
DopastonHMDB
DopastoneHMDB
DopastralHMDB
DopicarHMDB
DoprinHMDB
EldopalHMDB
EldoparHMDB
EldopatecHMDB
EurodopaHMDB
Helfo-dopaHMDB
InsulaminaHMDB
L-(-)-DopaHMDB
L-3-(3,4-Dihydroxyphenyl)-alanineHMDB
L-4-5-DihydroxyphenylalanineHMDB
L-b-(3,4-Dihydroxyphenyl)-a-alanineHMDB
L-beta-(3,4-Dihydroxyphenyl)-alpha-alanineHMDB
L-DihydroxyphenylalanineHMDB
LaradopaHMDB
LarodopaHMDB
LedopaHMDB
LevedopaHMDB
LevopaHMDB
MaipedopaHMDB
PardaHMDB
PardopaHMDB
ProdopaHMDB
SyndopaHMDB
VeldopaHMDB
WeldopaHMDB
3 Hydroxy L tyrosineHMDB
Roche brand OF levodopaHMDB
L 3,4 DihydroxyphenylalanineHMDB
L-3,4-DihydroxyphenylalanineHMDB
Medphano brand OF levodopaHMDB
L DopaHMDB
Roberts brand OF levodopaHMDB
Molecular FormulaC9H11NO4
Average Mass197.1879
Monoisotopic Mass197.068807845
IUPAC Name(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
Traditional Namelevodopa
CAS Registry NumberNot Available
SMILES
N[C@@H](CC1=CC=C(O)C(O)=C1)C(O)=O
InChI Identifier
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
InChI KeyWTDRDQBEARUVNC-LURJTMIESA-N