levodopa

Also known as 3,4-dihydroxy-L-phenylalanine, Sinemet®, L-3,4-dihydroxyphenylalanine, 3-Hydroxy-L-tyrosine, β-(3,4-dihydroxyphenyl)-L-alanine, Levodopum, β-(3,4-dihydroxyphenyl)alanine

-DOPA, also known as -3,4-dihydroxyphenylalanine and used medically as levodopa, is made and used as part of the normal biology of some plants and animals, including humans. Humans, as well as a portion of the other animals that utilize -DOPA, make it via biosynthesis from the amino acid -tyrosine.

Chemical data

Formula: C9H11NO4
Molecular weight: 197.19 g/mol
IUPAC name: (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
SMILES: C1=CC(=C(C=C1C[C@@H](C(=O)O)N)O)O
InChIKey: WTDRDQBEARUVNC-LURJTMIESA-N
XLogP: -2.7
Polar surface area: 104 Å²
H-bond donors: 4
H-bond acceptors: 5
Formal charge: 0

via PubChem

Wikidata facts

Mass: 197.069

Show 7 more facts

chemical formula: C₉H₁₁NO₄
Commons category: Levodopa
canonical SMILES: C1=CC(=C(C=C1CC(C(=O)O)N)O)O
isomeric SMILES: C1=CC(=C(C=C1C[C@@H](C(=O)O)N)O)O
World Health Organisation international non-proprietary name: levodopa
defined daily dose: 3.5
MCN code: 3003.90.45

Sources (10)

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Article

9 sections

Contents

Biological role
Chemistry
Synthesis
History
Other organisms
Marine adhesion
In plants and in the environment
Use as a medication and supplement
References

-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), which are collectively known as catecholamines. Furthermore, -DOPA itself mediates neurotrophic factor release by the brain and central nervous system. In some plant families (of the order Caryophyllales), -DOPA is the central precursor of a biosynthetic pathway that produces a class of pigments called betalains.