L-α-methyldopa   

GtoPdb Ligand ID: 5217

Synonyms: Aldomet® | Aldoril® | Dopamet® | L-α-Methyl-3,4-dihydroxyphenylalanine
L-α-methyldopa is an approved drug (FDA (1962))
Compound class: Synthetic organic
Comment: L-α-methyldopa is metabolised to α-methylnorepinephrine in the brain, the metabolite being a selective agonist of α2 adrenoceptors. Clinical L-α-methyldopa use has largely been replaced by safer alternatives.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 4
Rotatable bonds 3
Topological polar surface area 103.78
Molecular weight 211.08
XLogP -1.92
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OC(=O)C(Cc1ccc(c(c1)O)O)(N)C
Isomeric SMILES OC(=O)[C@](Cc1ccc(c(c1)O)O)(N)C
InChI InChI=1S/C10H13NO4/c1-10(11,9(14)15)5-6-2-3-7(12)8(13)4-6/h2-4,12-13H,5,11H2,1H3,(H,14,15)/t10-/m0/s1
InChI Key CJCSPKMFHVPWAR-JTQLQIEISA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1962))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
International Nonproprietary Names
INN number INN
1110 methyldopa
Synonyms
Aldomet® | Aldoril® | Dopamet® | L-α-Methyl-3,4-dihydroxyphenylalanine
Database Links
CAS Registry No. 555-30-6
ChEBI CHEBI:61058
ChEMBL Ligand CHEMBL459
DrugBank Ligand DB00968
DrugCentral Ligand 1762
GtoPdb PubChem SID 178101902
PubChem CID 38853
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Wikipedia Methyldopa

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Tocris
L-(-)-α-Methyldopa
Cat. No. 0584