Bluedark

L-DOPA
3,4-Dihydroxyphenylalanine
Molecular structure via molpic
Molecular formulaC9H11NO4
Molecular mass197.19 g/mol
Predicted LogP-2.7
Melting point270 °C
Solubility3.6 mg/mL
Chiralityracemic
Identifiers
[]
IUPAC name2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
SMILESC1=CC(=C(C=C1CC(C(=O)O)N)O)O
InChIInChI=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)
InChIKeyWTDRDQBEARUVNC-UHFFFAOYSA-N

3,4-Dihydroxyphenylalanine

3,4-Dihydroxyphenylalanine (also known as DL-DOPA, 3,4-Dihydroxy-DL-phenylalanine, 2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid, 3-(3,4-Dihydroxyphenyl)-DL-alanine, dihydroxyphenylalanine, 3-Hydroxytyrosine, DL-Dihydroxyphenylalanine, DL-Dioxyphenylalanine, DL-Tyrosine, 3-hydroxy- or 3-Hydroxy-DL-tyrosine) is a substance of the amino acid class.

Chemistry

Stereochemistry

DL-3,4-Dihydroxyphenylalanine is a racemic mixture of the logical stereoisomers:
Stereoisomers
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D-3,4-DihydroxyphenylalanineL-3,4-Dihydroxyphenylalanine
D-3,4-Dihydroxyphenylalanine L-3,4-Dihydroxyphenylalanine

Pharmacology

Predicted binding sites (SwissTargetPredictions)[]
TargetTarget ClassProbability
Sodium-dependent Norepinephrine Transporter0.43
Sodium-dependent Serotonin Transporter0.43
Sodium-dependent Dopamine Transporter0.43
Trace amine-associatedReceptor 10.43
Trace amine-associatedReceptor 20.43
Monoamine oxidase Enzyme A0.34
Monoamine oxidase Enzyme B0.34
Sigma non-opioid intracellularReceptor 10.34
SerotoninReceptor 2A0.30
SerotoninReceptor 2C0.30

See also