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Substance Name: Methyldopa [INN]
RN: 555-30-6
UNII: M4R0H12F6M
InChIKey: CJCSPKMFHVPWAR-JTQLQIEISA-N

Note

  • An alpha-2 adrenergic agonist that has both central and peripheral nervous system effects. Its primary clinical use is as an antihypertensive agent.

Molecular Formula

  • C10-H13-N-O4

Molecular Weight

  • 211.2157
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic Agonists
  • Adrenergic alpha-2 Receptor Agonists
  • Adrenergic alpha-Agonists
  • Antihypertensive Agents
  • Autonomic Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sympatholytics

Names and Synonyms

Results Name

  • Methyldopa [INN]

Name of Substance

  • Methyldopa
  • Methyldopa (anhydrous)
  • Methyldopa [INN]

MeSH Heading

  • Methyldopa

Synonyms

  • (S)-(-)-alpha-Methyldopa
  • 3-Hydroxy-alpha-methyl-L-tyrosine
  • Alanine, 3-(3,4-dihydroxyphenyl)-2-methyl-, L-(-)-
  • Aldomet
  • Aldometil
  • Aldomin
  • alpha Medopa
  • alpha-Methyl dopa
  • alpha-Methyl-beta-(3,4-dihydroxyphenyl)-L-alanine
  • alpha-Methyl-L-3,4-dihydroxyphenylalanine
  • alpha-Methyldihydroxyphenylalanine
  • alpha-Methyldopa (VAN)
  • Alphamethyldopa
  • AMD
  • Bayer 1440 L
  • Baypresol
  • Becanta
  • CCRIS 4671
  • Dopamet
  • Dopamethyperpax
  • Dopatec
  • Dopegit
  • Dopegyt
  • EINECS 209-089-2
  • Grospisk
  • HSDB 218
  • Hyperpax
  • Hypolag
  • L(-)-beta-(3,4-Dihydroxyphenyl)-alpha-methylalanine
  • L-(-)-3-(3,4-Dihydroxyphenyl)-2-methylalanine
  • L-(-)-alpha-Methyl-beta-(3,4-dihydroxyphenyl)alanine
  • L-(alpha-Md)
  • L-2-Amino-2-methyl-3-(3,4-dihydroxyphenyl)propionic acid
  • l-3-(3,4-Dihydroxyphenyl)-2-methylalanine
  • L-alpha-Methyl-3,4-dihydroxyphenylalanine
  • L-alpha-Methyldopa
  • L-Methyldopa
  • L-Tyrosine, 3-hydroxy-alpha-methyl-
  • levo-3-(3,4-Dihydroxyphenyl)-2-methylalanine
  • Medomet
  • Medopa
  • Medopal
  • Medopren
  • Methoplain
  • Methyl-L-dopa
  • Methyldopa
  • Methyldopum
  • Methyldopum [INN-Latin]
  • Metildopa
  • Metildopa [INN-Spanish]
  • MK 351
  • NCI-C55721
  • Nr.C 2294
  • NSC 169916
  • Presinol
  • Presolisin
  • Sedometil
  • Sembrina
  • UNII-M4R0H12F6M

Systematic Names

  • Alanine, 3-(3,4-dihydroxyphenyl)-2-methyl-, L-(-)-
  • L-Tyrosine, 3-hydroxy-alpha-methyl-
  • Methyl dopa
  • Methyldopa

Registry Numbers

CAS Registry Number

  • 555-30-6

FDA UNII

  • M4R0H12F6M

Other Registry Numbers

  • 133161-54-3
  • 1339-75-9
  • 4290-08-8
  • 779-08-8
  • 88620-56-8

System Generated Number

  • 0000555306

Structure Descriptors

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 1071mg/kg/22W (1071mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" CUTIS; Cutaneous Medicine for the Practitioner. Vol. 38, Pg. 187, 1986.
mouse LD50 intraperitoneal 150mg/kg (150mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Journal of Medicinal Chemistry. Vol. 20, Pg. 1378, 1977.
mouse LD50 intravenous 1700mg/kg (1700mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 56, Pg. 1103, 1960.
mouse LD50 oral 5300mg/kg (5300mg/kg)   Drugs in Japan Vol. -, Pg. 1178, 1990.
rabbit LD50 intravenous 713mg/kg (713mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 348, 1972.
rabbit LD50 oral 713mg/kg (713mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 162, 1973.
rat LD50 intraperitoneal 300mg/kg (300mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 348, 1972.
rat LD50 oral 5gm/kg (5000mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 348, 1972.
women TDLo oral 900mg/kg/13W- (900mg/kg) BEHAVIORAL: TREMOR Neurology. Vol. 35, Pg. 1668, 1985.
women TDLo oral 1830mg/kg/17W (1830mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

PERIPHERAL NERVE AND SENSATION: FASCICULATIONS
South African Medical Journal. Vol. 65, Pg. 194, 1984.
women TDLo oral 44gm/kg/3Y-I (44000mg/kg) GASTROINTESTINAL: NECROTIC GHANGES American Heart Journal. Vol. 105, Pg. 1037, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 300 dec deg C   EXP
log P (octanol-water) -1.790 (none)   EST
Water Solubility 1.00E+04 mg/L 25 EXP
Vapor Pressure 7.60E-11 mm Hg 25 EST
Henry's Law Constant 1.70E-18 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 8.01E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.