Record Information
Version1.0
Creation date2011-09-21 01:39:36 UTC
Update date2015-07-21 06:59:25 UTC
Primary IDFDB028425
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. from wiki [HMDB]
CAS Number555-30-6
Structure
Thumb
Synonyms
SynonymSource
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acidChEBI
(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
AldometKegg
(2S)-2-Amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoateGenerator
(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, Generator
Aldoclor-150HMDB
Aldoclor-250HMDB
AldometilHMDB
Aldoril 15HMDB
Aldoril 25HMDB
Aldoril D30HMDB
Aldoril D50HMDB
alpha-Methyl-L-dopaHMDB, MeSH
apo Methyldopa tab 125MGHMDB
apo Methyldopa tab 250MGHMDB
apo Methyldopa tab 500MGHMDB
apo-MethyldopaHMDB, MeSH
Bayer 1440 LHMDB
BaypresolHMDB
BecantaHMDB
DopametHMDB, MeSH
DopamethyperpaxHMDB
DopatecHMDB
DopegytHMDB, MeSH
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, MeSH
Methyldopate HCLHMDB
novo-Medopa tab 125MGHMDB
novo-Medopa tab 250MGHMDB
novo-Medopa tab 500MGHMDB
NovomedopaHMDB
Nu-medopaHMDB, MeSH
Nu-medopa tab 125MGHMDB
Nu-medopa tab 250MGHMDB
Nu-medopa tab 500MGHMDB
PresinolHMDB
PresolisinHMDB
SedometilHMDB
SembrinaHMDB, MeSH
Alphapharm brand OF methyldopaMeSH, HMDB
Apotex brand OF methyldopaMeSH, HMDB
Merck brand OF methyldopaMeSH, HMDB
Nu pharm brand OF methyldopaMeSH, HMDB
DopergitMeSH, HMDB
HydopaMeSH, HMDB
Merck sharp and dohme brand OF methyldopaMeSH, HMDB
Methyldopa orion brandMeSH, HMDB
Nu-pharm brand OF methyldopaMeSH, HMDB
Orion brand OF methyldopaMeSH, HMDB
Rhône poulenc rorer brand OF methyldopaMeSH, HMDB
Rhône-poulenc rorer brand OF methyldopaMeSH, HMDB
DopegitMeSH, HMDB
Methyldopa apotex brandMeSH, HMDB
Methyldopa biopat brandMeSH, HMDB
Methyldopa clonmel brandMeSH, HMDB
Methyldopa merck brandMeSH, HMDB
Nu medopaMeSH, HMDB
alpha Methyl L dopaMeSH, HMDB
alpha MethyldopaMeSH, HMDB
apo MethyldopaMeSH, HMDB
Biopat brand OF methyldopaMeSH, HMDB
Cahill may roberts brand OF methyldopaMeSH, HMDB
Clonmel brand OF methyldopaMeSH, HMDB
MeldopaMeSH, HMDB
Methyldopa alphapharm brandMeSH, HMDB
Methyldopa nu-pharm brandMeSH, HMDB
MethyldopaChEBI
Α-methyl-L-dopaGenerator, HMDB
(-)-a-methyldopahmdb
(-)-alpha-methyldopahmdb
(-)-methyldopahmdb
(s)-(-)-a-methyldopahmdb
(s)-(-)-alpha-methyldopahmdb
(S)-(-)-α-methyldopaGenerator
3,4-dihydroxy-2-methylphenylalanine (ACD/Name 4.0)hmdb
a-methyl dopahmdb
a-methyl-l-dopahmdb
a-methyldopa (van)hmdb
Alpha medopahmdb
alpha-methyl dopahmdb
alpha-methyl-l-dopahmdb
alpha-methyldopa (van)hmdb
Apo Methyldopa Tab 125mghmdb
Apo Methyldopa Tab 250mghmdb
Apo Methyldopa Tab 500mghmdb
Apo-methyldopahmdb
L-(-)-3-(3,4-dihydroxyphenyl)-2-methyl-Alaninehmdb
L-(-)-a-methyl-a-methyl-Aldominhmdb
L-(-)-alpha-methyl-alpha-methyl-Aldominhmdb
L-(-)-α-methyl-β-(3,4-dihydroxyphenyl)alanineGenerator
L-(alpha-Md)ChEBI
L-(α-md)Generator
L-2-amino-2-Methyl-3-(3,4-dihydroxyphenyl)propionateGenerator
L-2-amino-2-Methyl-3-(3,4-dihydroxyphenyl)propionic acidChEBI
l-a-methyldopahmdb
l-alpha-methyldopahmdb
L-methyl dopahmdb
L-α-methyl-3,4-dihydroxyphenylalanineGenerator
L-α-methyldopaGenerator
L(-)-a-methylalaninehmdb
L(-)-alpha-methylalaninehmdb
L(-)-β-(3,4-dihydroxyphenyl)-α-methylalanineGenerator
Methyldopa 125 Tab 125mghmdb
Methyldopa 250 Tabhmdb
Methyldopa 500 Tab 500mghmdb
Novo-Medopa Tab 125mghmdb
Novo-Medopa Tab 250mghmdb
Novo-Medopa Tab 500mghmdb
Nu-Medopa Tab 125mghmdb
Nu-Medopa Tab 250mghmdb
Nu-Medopa Tab 500mghmdb
α medopaGenerator
α-methyl dopaGenerator
α-methyl-L-3,4-dihydroxyphenylalanineGenerator
α-methyl-β-(3,4-dihydroxyphenyl)-L-alanineGenerator
α-methyldihydroxyphenylalanineGenerator
α-methyldopaGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H13NO4
IUPAC name(2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
InChI IdentifierInChI=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
Isomeric SMILESC[C@](N)(CC1=CC=C(O)C(O)=C1)C(O)=O
Average Molecular Weight211.2145
Monoisotopic Molecular Weight211.084457909
Classification
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids 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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSMethyldopa, non-derivatized, GC-MS Spectrumsplash10-001i-0690000000-f54d986a8144f4a79b82Spectrum
GC-MSMethyldopa, non-derivatized, GC-MS Spectrumsplash10-001i-0690000000-f54d986a8144f4a79b82Spectrum
Predicted GC-MSMethyldopa, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xu-4900000000-739bef9b92ae61fa3997Spectrum
Predicted GC-MSMethyldopa, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03l3-6719300000-8507376d6ae27047f468Spectrum
Predicted GC-MSMethyldopa, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0g5i-2900000000-2d1c0ec9ad93e208b6202017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0g5i-2900000000-2d1c0ec9ad93e208b6202017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-01p2-3940000000-04fec0e15e79c768fdc72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0002-2910000000-5ab87bad3301cc12d6712021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0wmi-5900000000-8d84c2b3f8d9068136682021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0ik9-2900000000-f0762b6c346fb34404e52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014s-0910000000-ef3d681f544c504b6f072021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014r-0900000000-a11a3fc0536274091e7c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-03y0-0900000000-20bad18343ec957bca952021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-014r-0900000000-2a78e6a20d8599caab2b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014s-0910000000-db2e7c58eec2a2e9f25e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-03y0-0900000000-4ee772845ee32a944db12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0002-1900000000-3efdf92a8af6e42965e22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0002-1900000000-4ba9f4555cda937d38832021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-006t-1900000000-aa6c8ce94351767534b12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0002-0900000000-cdcf4d0d2fe21483aac52021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0910000000-3bfdb36173438fdd8a172016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-9b6b615025e3da8f54502016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0600-4900000000-34dc05f00879ecc053bf2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0910000000-3bfdb36173438fdd8a172016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-9b6b615025e3da8f54502016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0600-4900000000-34dc05f00879ecc053bf2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4290000000-cdd2c737cabf0ee44d1f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9410000000-d1fa6c265dd8ca539a0e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007d-6900000000-56bdd61262b97efe050b2016-08-03View Spectrum
NMRNot Available
ChemSpider ID35562
ChEMBL IDCHEMBL459
KEGG Compound IDC07194
Pubchem Compound ID38853
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11754
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMethyldopa
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference