You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-03-17 14:11:07 UTC
Update Date2018-05-18 01:54:04 UTC
HMDB IDHMDB0011754
Secondary Accession Numbers
  • HMDB11754
Metabolite Identification
Common NameMethyldopa
DescriptionMethyldopa or alpha-methyldopa (brand names Aldomet, Apo-Methyldopa, Dopamet, Novomedopa) is a centrally-acting adrenergic antihypertensive medication. Its use is now deprecated following introduction of alternative safer classes of agents. However it continues to have a role in otherwise difficult to treat hypertension and gestational hypertension (formerly known as pregnancy-induced hypertension). Methyldopa is an aromatic-amino-acid decarboxylase inhibitor in animals and in man. Only methyldopa, the L-isomer of alpha-methyldopa, has the ability to inhibit dopa decarboxylase and to deplete animal tissues of norepinephrine. In man the antihypertensive activity appears to be due solely to the L-isomer. About twice the dose of the racemate (DL-alpha-methyldopa) is required for equal antihypertensive effect. Methyldopa has no direct effect on cardiac function and usually does not reduce glomerular filtration rate, renal blood flow, or filtration fraction. Cardiac output usually is maintained without cardiac acceleration. In some patients the heart rate is slowed. Normal or elevated plasma renin activity may decrease in the course of methyldopa therapy. Methyldopa reduces both supine and standing blood pressure. Methyldopa usually produces highly effective lowering of the supine pressure with infrequent symptomatic postural hypotension. Exercise hypotension and diurnal blood pressure variations rarely occur. Methyldopa, in its active metabolite form, is a central alpha-2 receptor agonist. Using methyldopa leads to alpha-2 receptor-negative feedback to sympathetic nervous system (SNS) (centrally and peripherally), allowing peripheral sympathetic nervous system tone to decrease. Such activity leads to a decrease in total peripheral resistance (TPR) and cardiac output. When introduced it was a mainstay of antihypertensive therapy, but its use has declined, with increased use of other safer classes of agents. One of its important present-day uses is in the management of pregnancy-induced hypertension, as it is relatively safe in pregnancy compared to other antihypertensive drugs (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
(S)-(-)-alpha-MethyldopaChEBI
3-Hydroxy-alpha-methyl-L-tyrosineChEBI
Alpha MedopaChEBI
alpha-Methyl dopaChEBI
alpha-Methyl-beta-(3,4-dihydroxyphenyl)-L-alanineChEBI
alpha-Methyl-L-3,4-dihydroxyphenylalanineChEBI
alpha-MethyldihydroxyphenylalanineChEBI
alpha-MethyldopaChEBI
AlphamethyldopaChEBI
AMDChEBI
L(-)-beta-(3,4-Dihydroxyphenyl)-alpha-methylalanineChEBI
L-(-)-3-(3,4-Dihydroxyphenyl)-2-methylalanineChEBI
L-(-)-alpha-Methyl-beta-(3,4-dihydroxyphenyl)alanineChEBI
L-(alpha-MD)ChEBI
L-2-amino-2-Methyl-3-(3,4-dihydroxyphenyl)propionic acidChEBI
L-3-(3,4-Dihydroxyphenyl)-2-methylalanineChEBI
L-alpha-Methyl-3,4-dihydroxyphenylalanineChEBI
L-alpha-MethyldopaChEBI
L-Methyl dopaChEBI
levo-3-(3,4-Dihydroxyphenyl)-2-methylalanineChEBI
Methyl-L-dopaChEBI
Methyldopa anhydrousChEBI
MethyldopumChEBI
MetildopaChEBI
(S)-(-)-a-MethyldopaGenerator
(S)-(-)-α-methyldopaGenerator
3-Hydroxy-a-methyl-L-tyrosineGenerator
3-Hydroxy-α-methyl-L-tyrosineGenerator
a MedopaGenerator
α medopaGenerator
a-Methyl dopaGenerator
α-methyl dopaGenerator
a-Methyl-b-(3,4-dihydroxyphenyl)-L-alanineGenerator
α-methyl-β-(3,4-dihydroxyphenyl)-L-alanineGenerator
a-Methyl-L-3,4-dihydroxyphenylalanineGenerator
α-methyl-L-3,4-dihydroxyphenylalanineGenerator
a-MethyldihydroxyphenylalanineGenerator
α-methyldihydroxyphenylalanineGenerator
a-MethyldopaGenerator
α-methyldopaGenerator
L(-)-b-(3,4-Dihydroxyphenyl)-a-methylalanineGenerator
L(-)-β-(3,4-dihydroxyphenyl)-α-methylalanineGenerator
L-(-)-a-Methyl-b-(3,4-dihydroxyphenyl)alanineGenerator
L-(-)-α-methyl-β-(3,4-dihydroxyphenyl)alanineGenerator
L-(a-MD)Generator
L-(α-MD)Generator
L-2-amino-2-Methyl-3-(3,4-dihydroxyphenyl)propionateGenerator
L-a-Methyl-3,4-dihydroxyphenylalanineGenerator
L-α-methyl-3,4-dihydroxyphenylalanineGenerator
L-a-MethyldopaGenerator
L-α-methyldopaGenerator
(-)-a-MethyldopaHMDB
(-)-alpha-MethyldopaHMDB
(-)-MethyldopaHMDB
2-Methyl-3-(3,4-dihydroxyphenyl)alanineHMDB
3,4-Dihydroxy-2-methylphenylalanine (acd/name 4.0)HMDB
a-Methyl-L-dopaHMDB
Aldoclor-150HMDB
Aldoclor-250HMDB
AldometHMDB
AldometilHMDB
Aldoril 15HMDB
Aldoril 25HMDB
Aldoril D30HMDB
Aldoril D50HMDB
alpha-Methyl-L-dopaHMDB
apo Methyldopa tab 125MGHMDB
apo Methyldopa tab 250MGHMDB
apo Methyldopa tab 500MGHMDB
apo-MethyldopaHMDB
Bayer 1440 LHMDB
BaypresolHMDB
BecantaHMDB
DopametHMDB
DopamethyperpaxHMDB
DopatecHMDB
DopegytHMDB
GrospiskHMDB
HyperpaxHMDB
HypolagHMDB
L(-)-a-MethylalanineHMDB
L(-)-alpha-MethylalanineHMDB
L-(-)-3-(3,4-Dihydroxyphenyl)-2-methyl-alanineHMDB
L-(-)-a-Methyl-a-methyl-aldominHMDB
L-(-)-alpha-Methyl-alpha-methyl-aldominHMDB
L-a-Methyl-(3, 4-dihydroxyphenyl)alanineHMDB
L-alpha-Methyl-(3, 4-dihydroxyphenyl)alanineHMDB
MedometHMDB
MedopaHMDB
MedopalHMDB
MedoprenHMDB
MethoplainHMDB
Methyldopa 125 tab 125MGHMDB
Methyldopa 250 tabHMDB
Methyldopa 500 tab 500MGHMDB
MethyldopateHMDB
Methyldopate HCLHMDB
novo-Medopa tab 125MGHMDB
novo-Medopa tab 250MGHMDB
novo-Medopa tab 500MGHMDB
NovomedopaHMDB
Nu-medopaHMDB
Nu-medopa tab 125MGHMDB
Nu-medopa tab 250MGHMDB
Nu-medopa tab 500MGHMDB
PresinolHMDB
PresolisinHMDB
SedometilHMDB
SembrinaHMDB
Alphapharm brand OF methyldopaMeSH
Apotex brand OF methyldopaMeSH
Merck brand OF methyldopaMeSH
Nu pharm brand OF methyldopaMeSH
DopergitMeSH
HydopaMeSH
Merck sharp and dohme brand OF methyldopaMeSH
Methyldopa orion brandMeSH
Nu-pharm brand OF methyldopaMeSH
Orion brand OF methyldopaMeSH
Rhône poulenc rorer brand OF methyldopaMeSH
Rhône-poulenc rorer brand OF methyldopaMeSH
DopegitMeSH
Methyldopa apotex brandMeSH
Methyldopa biopat brandMeSH
Methyldopa clonmel brandMeSH
Methyldopa merck brandMeSH
Nu medopaMeSH
alpha Methyl L dopaMeSH
alpha MethyldopaMeSH
apo MethyldopaMeSH
Biopat brand OF methyldopaMeSH
Cahill may roberts brand OF methyldopaMeSH
Clonmel brand OF methyldopaMeSH
MeldopaMeSH
Methyldopa alphapharm brandMeSH
Methyldopa nu-pharm brandMeSH
Chemical FormulaC10H13NO4
Average Molecular Weight211.2145
Monoisotopic Molecular Weight211.084457909
IUPAC Name(2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
Traditional Namemethyldopa
CAS Registry Number555-30-6
SMILES
C[C@](N)(CC1=CC=C(O)C(O)=C1)C(O)=O
InChI Identifier
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 KeyCJCSPKMFHVPWAR-JTQLQIEISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • D-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Phenylpropane
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10 at 25 °CNot Available
LogP-1.79MEYLAN,WM & HOWARD,PH (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.26 g/LALOGPS
logP-2ALOGPS
logP-1.4ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)9.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.78 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.79 m³·mol⁻¹ChemAxon
Polarizability20.73 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0690000000-f54d986a8144f4a79b82View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0690000000-f54d986a8144f4a79b82View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xu-4900000000-739bef9b92ae61fa3997View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03l3-6719300000-8507376d6ae27047f468View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0g5i-2900000000-2d1c0ec9ad93e208b620View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0g5i-2900000000-2d1c0ec9ad93e208b620View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0910000000-3bfdb36173438fdd8a17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-9b6b615025e3da8f5450View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0600-4900000000-34dc05f00879ecc053bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0910000000-3bfdb36173438fdd8a17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-9b6b615025e3da8f5450View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0600-4900000000-34dc05f00879ecc053bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4290000000-cdd2c737cabf0ee44d1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9410000000-d1fa6c265dd8ca539a0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007d-6900000000-56bdd61262b97efe050bView in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.5 (0.0-1.0) umol/mmol creatinineAdult (>18 years old)Both
Prostate Cancer
details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDDB00968
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028425
KNApSAcK IDNot Available
Chemspider ID35562
KEGG Compound IDC07194
BioCyc IDALPHA-METHYLDOPA
BiGG IDNot Available
Wikipedia LinkMethyldopa
METLIN IDNot Available
PubChem Compound38853
PDB IDNot Available
ChEBI ID61058
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Iyer KS, Thampuran RV: Beta blockade and anticonvulsant activity of propranolol. Indian J Physiol Pharmacol. 1978 Jul-Sep;22(3):293-6. [PubMed:721251 ]

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
Methyldopa → (2S)-2-amino-3-(4-hydroxy-3-methoxyphenyl)-2-methylpropanoic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Methyldopa → 6-{5-[(2S)-2-amino-2-carboxy-2-methylethyl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Methyldopa → 6-{4-[(2R)-2-amino-2-carboxy-2-methylethyl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Methyldopa → (2S)-2-amino-3-[4-hydroxy-3-(sulfooxy)phenyl]-2-methylpropanoic aciddetails