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CAS No 555-30-6 , (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

  • Name: (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
  • Synonyms: Dopamet; Baypresol; Sedometil;(2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid; Sembrina; Alphamethyldopa;Aldomet; Dopegyt; Presolisin; Hyperpax;
  • CAS Registry Number:
  • Melting Point: ≥300 °C
  • Flash Point: 220.9°C
  • Boiling Point: 441.6°Cat760mmHg
  • Density: 1.403g/cm3
  • Refractive index: -14 ° (C=1, H2O)
  • Safety Statements: Poison by intraperitoneal route. Moderately toxic by ingestion and intravenous routes. Human systemic effects by ingestion: fasciculations, hallucinations, distorted perceptions, tremors, allergic dermatitis, necrotic gastrointestinal changes. An experimental teratogen. Human reproductive effects: menstrual cycle changes or disorders, effects on newborn including abnormal neonatal measures and growth statistics, biochemical and metabolic changes. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
  • Flash Point: 220.9°C
  • EINECS: 209-089-2
  • Molecular Weight: 211.21452
  • InchiKey: CJCSPKMFHVPWAR-JTQLQIEISA-N
  • 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
  • Risk Statements: S24/25:Avoidcontactwithskinandeyes.;
  • Molecular Formula: C10H13NO4
  • Molecular Structure:CAS No:555-30-6 (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

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References of (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
Title: Methyldopa
CAS Registry Number: 555-30-6
CAS Name: 3-Hydroxy-a-methyl-L-tyrosine
Synonyms: L-3-(3,4-dihydroxyphenyl)-2-methylalanine; L-a-methyl-3,4-dihydroxyphenylalanine; L-2-amino-2-methyl-3-(3,4-dihydroxyphenyl)propionic acid; a-methyldopa; AMD
Manufacturers' Codes: MK-351
Trademarks: Aldomet (Merck & Co.); Aldomin (Merck & Co.); Dopamet (Dumex); Dopegyt (Egis); Elanpres (Elan); Equibar (Aventis); Medopren (Malesci); Methoplain (Kowa Yakuhin); Sembrina (Orion); Presinol (Bayer)
Molecular Formula: C10H13NO4
Molecular Weight: 211.21
Percent Composition: C 56.87%, H 6.20%, N 6.63%, O 30.30%
Literature References: Exists as the sesquihydrate. Prepn: Pfister, Stein, US 2868818 (1959 to Merck & Co.). Resolution: Jones et al., US 3158648 (1964 to Merck & Co.); cf. Slates et al., J. Org. Chem. 29, 1424 (1964). Resolution and configuration: Tristram, ibid. 2053. Synthesis from asymmetric intermediates: Reinhold et al., J. Org. Chem. 33, 1209 (1968). Prepn of the ethyl ester hydrochloride: FR M2153 (1963 to Merck & Co.); of pharmaceutical dosage forms: Marcus, US 3230143 (1966 to Merck & Co.). Mode of action: Finch, Haeusler, Br. J. Pharmacol. 45, 167p (1972); Day et al., ibid. 168p. Review of pharmacology: A. Scriabine, Ed. in Pharmacology of Antihypertensive Drugs (Raven, New York, 1980) pp 43-54.
 
Derivative Type: L-Form sesquihydrate
Properties: Crystals from water. Minute anhydr crystals from methanol, considerably hygroscopic, dec ~300°. [a]D23 -4.0 ± 0.5° (c = 1 in 0.1N HCl). uv max: 281 nm (e 2780). Soly in water at 25°: ~10 mg/ml. pH of satd aq soln about 5.0. (Soly of D-form in water at 25°: ~10 mg/ml, of DL-form: ~18 mg/ml) Practically insol in the common organic solvents. Sol in dil mineral acids.
Optical Rotation: [a]D23 -4.0 ± 0.5° (c = 1 in 0.1N HCl)
Absorption maximum: uv max: 281 nm (e 2780)
 
Derivative Type: Ethyl ester hydrochloride
CAS Registry Number: 2508-79-4
Synonyms: Methyldopate hydrochloride
Molecular Formula: C12H18ClNO4
Molecular Weight: 275.73
Percent Composition: C 52.27%, H 6.58%, Cl 12.86%, N 5.08%, O 23.21%
Properties: After drying, mol wt 275.7 (1 mg = 0.77 mg of the free acid). Soluble in water to the extent of 10-300 mg/ml at pH 2-7. May be stabilized with sodium bisulfite and/or disodium EDTA.
 
Therap-Cat: Antihypertensive.
Keywords: Antihypertensive.