alpha-methyl-L-dopa (CHEBI:61058)

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ChEBI Name	α-methyl-L-dopa

ChEBI ID	CHEBI:61058

ChEBI ASCII Name	alpha-methyl-L-dopa

Definition	A derivative of L-tyrosine having a methyl group at the α-position and an additional hydroxy group at the 3-position on the phenyl ring.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C10H13NO4

Net Charge

Average Mass

211.21450

Monoisotopic Mass

211.08446

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

InChIKey

CJCSPKMFHVPWAR-JTQLQIEISA-N

SMILES

C[C@](N)(Cc1ccc(O)c(O)c1)C(O)=O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	sympatholytic agent Any compound which inhibits the postganglionic functioning of the sympathetic nervous system (SNS). hapten Any substance capable of eliciting an immune response only when attached to a large carrier such as a protein. Examples include dinitrophenols; oligosaccharides; peptides; and heavy metals. alpha-adrenergic agonist An agent that selectively binds to and activates alpha-adrenergic receptors.

Application(s):	sympatholytic agent Any compound which inhibits the postganglionic functioning of the sympathetic nervous system (SNS). antihypertensive agent Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism. alpha-adrenergic agonist An agent that selectively binds to and activates alpha-adrenergic receptors. peripheral nervous system drug A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.

ChEBI Ontology
Outgoing	α-methyl-L-dopa (CHEBI:61058) has role α-adrenergic agonist (CHEBI:35569) α-methyl-L-dopa (CHEBI:61058) has role antihypertensive agent (CHEBI:35674) α-methyl-L-dopa (CHEBI:61058) has role hapten (CHEBI:59174) α-methyl-L-dopa (CHEBI:61058) has role peripheral nervous system drug (CHEBI:49110) α-methyl-L-dopa (CHEBI:61058) has role sympatholytic agent (CHEBI:66991) α-methyl-L-dopa (CHEBI:61058) is a L-tyrosine derivative (CHEBI:27177) α-methyl-L-dopa (CHEBI:61058) is a non-proteinogenic L-α-amino acid (CHEBI:83822)

Incoming	α-methyl-L-dopa ethyl ester (CHEBI:94761) has functional parent α-methyl-L-dopa (CHEBI:61058) 3-methoxy-α-methyl-L-tyrosine (CHEBI:141143) has functional parent α-methyl-L-dopa (CHEBI:61058)

IUPAC Name

3-hydroxy-α-methyl-L-tyrosine

Synonyms	Sources
(2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid	IUPAC
(S)-(-)-alpha-Methyldopa	ChemIDplus
3-Hydroxy-alpha-methyl-L-tyrosine	ChemIDplus
Alpha medopa	DrugBank
alpha-Methyl dopa	ChemIDplus
alpha-Methyl-beta-(3,4-dihydroxyphenyl)-L-alanine	ChemIDplus
alpha-Methyl-L-3,4-dihydroxyphenylalanine	ChemIDplus
alpha-Methyldihydroxyphenylalanine	ChemIDplus
alpha-Methyldopa	ChemIDplus
Alphamethyldopa	DrugBank
AMD	DrugBank
L(-)-beta-(3,4-Dihydroxyphenyl)-alpha-methylalanine	ChemIDplus
L-(-)-3-(3,4-Dihydroxyphenyl)-2-methylalanine	ChemIDplus
L-(-)-alpha-Methyl-beta-(3,4-dihydroxyphenyl)alanine	ChemIDplus
L-(alpha-Md)	ChemIDplus
L-2-Amino-2-methyl-3-(3,4-dihydroxyphenyl)propionic acid	ChemIDplus
l-3-(3,4-Dihydroxyphenyl)-2-methylalanine	ChemIDplus
L-alpha-Methyl-3,4-dihydroxyphenylalanine	ChemIDplus
L-alpha-Methyldopa	ChemIDplus
L-Methyl Dopa	DrugBank
levo-3-(3,4-Dihydroxyphenyl)-2-methylalanine	ChemIDplus
Methyl-L-dopa	ChemIDplus
Methyldopa	KEGG COMPOUND
Methyldopa anhydrous	DrugBank

Last Modified

28 June 2022

General Comment
2011-01-19	Primary clinical use is as an antihypertensive agent.