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Record Information
Version3.6
Creation Date2009-03-17 14:11:07 UTC
Update Date2016-02-11 01:22:12 UTC
HMDB IDHMDB11754
Secondary Accession NumbersNone
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
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(O)=C(O)C=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 KeyInChIKey=CJCSPKMFHVPWAR-JTQLQIEISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as catecholamines and derivatives. These are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentCatecholamines and derivatives
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Catecholamine
  • L-alpha-amino acid
  • D-alpha-amino acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Phenylpropane
  • Aralkylamine
  • Amino fatty acid
  • Fatty acyl
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10mg/mL at 25 °CNot Available
LogP-1.79MEYLAN,WM & HOWARD,PH (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.26 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.79 m3·mol-1ChemAxon
Polarizability20.73 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.5 (0.0-1.0) umol/mmol creatinineAdult (>18 years old)Both
Prostate Cancer
details
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-5 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-5 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 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. [19212411 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028425
KNApSAcK IDNot Available
Chemspider ID35562
KEGG Compound IDC07194
BioCyc IDALPHA-METHYLDOPA
BiGG IDNot Available
Wikipedia LinkMethyldopa
NuGOwiki LinkHMDB11754
Metagene LinkHMDB11754
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. [721251 ]