L-Tyrosine, 3-hydroxy-a-methyl-

When methyldopa was first introduced, it was the mainstay of antihypertensive treatment, but its use has declined on account of relatively severe adverse side effects, with increased use of other safer and more tolerable agents such as alpha blockers, beta blockers, and calcium channel blockers. Nonetheless, one of methyldopa's still current indications is in the management of pregnancy-induced hypertension (PIH), as it is relatively safe in pregnancy compared to many other antihypertensives which may affect the fetus.

The IUPAC name of Methyldopa is (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid. With the CAS registry number 555-30-6, it is also named as 3-Hydroxy-alpha-methyl-L-tyrosine. The product's category is API's, and the other registry numbers are 133161-54-3; 1339-75-9; 4290-08-8; 779-08-8; 88620-56-8. Besides, it is white to yellowish-white fine powder that may be sensitive to prolonged exposure to air and light. In addition, its molecular formula is C₁₀H₁₃NO₄ and molecular weight is 211.22.

The other characteristics of this product can be summarized as: (1)EINECS: 209-089-2; (2)ACD/LogP: 0.13; (3)# of Rule of 5 Violations: 1; (4)ACD/LogD (pH 5.5): -2.37; (5)ACD/LogD (pH 7.4): -2.39; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 1; (9)ACD/KOC (pH 7.4): 1; (10)#H bond acceptors: 5; (11)#H bond donors: 5; (12)#Freely Rotating Bonds: 6; (13)Index of Refraction: 1.635; (14)Molar Refractivity: 53.89 cm³; (15)Molar Volume: 150.4 cm³; (16)Surface Tension: 72.6 dyne/cm; (17)Density: 1.403 g/cm³; (18)Flash Point: 220.9 °C; (19)Melting Point: 300 °C; (20)Water Solubility: 1.00E+04 mg/L at 25 °C; (21)Enthalpy of Vaporization: 73.67 kJ/mol; (22)Boiling Point: 441.6 °C at 760 mmHg; (23)Vapour Pressure: 1.41E-08 mmHg at 25 °C.

Preparation of Methyldopa: frist, you can use Vanillin to produce Veratraldehyde by the reaction with Dimethyl sulfate. Then use it to react with Nitroethane, and then deoxidate by the use of iron powder. And you will obtain 3-Hydroxy-alpha-methyl-DL-tyrosine after cyclization, ring-opening and hydrolysis reaction. At last, you will get this chemical by the resolution of levorotatory.

Uses of Methyldopa: this chemical is a alpha-adrenergic agonist psychoactive drug used as a sympatholytic or antihypertensive. It is also used in the clinical treatment of high blood pressure, preeclampsia and pregnancy-induced hypertension. Additionally, it is a competitive inhibitor of the enzyme DOPA decarboxylase. It is converted to α-Methylnorepinephrine by dopamine beta-hydroxylase (DBH). α-Methylnorepinephrine is an agonist of presynaptic central nervous system α2-adrenergic receptors.

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C(O)[C@@](N)(Cc1cc(O)c(O)cc1)C
(2)InChI: InChI=1/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
(3)InChIKey: CJCSPKMFHVPWAR-JTQLQIEIBS

The toxicity data is as follows: