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Methyldopa

Methyldopa
Methyldopa structure
CAS No.
555-30-6
Chemical Name:
Methyldopa
Synonyms
amd;mkb51;MK-351;MEDOBA;aldomet;aldomin;dopamet;dopatec;dopegyt;medomet
CBNumber:
CB4277127
Molecular Formula:
C10H13NO4
Formula Weight:
211.21
MOL File:
555-30-6.mol

Methyldopa Properties

Melting point:
≥300 °C
Boiling point:
350.89°C (rough estimate)
Density 
1.2545 (rough estimate)
refractive index 
-14 ° (C=1, H2O)
storage temp. 
Store at RT
Merck 
14,6055
CAS DataBase Reference
555-30-6(CAS DataBase Reference)
EPA Substance Registry System
L-Tyrosine, 3-hydroxy-.alpha.-methyl-(555-30-6)
SAFETY
  • Risk and Safety Statements
WGK Germany  3
RTECS  YP2860000
10-23
HS Code  29181990

Methyldopa price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical D1817 3-(3,4-Dihydroxyphenyl)-2-methyl-L-alanine Sesquihydrate >98.0%(HPLC)(T) 555-30-6 5g $60 2018-11-22 Buy
TCI Chemical D1817 3-(3,4-Dihydroxyphenyl)-2-methyl-L-alanine Sesquihydrate >98.0%(HPLC)(T) 555-30-6 25g $180 2018-11-22 Buy
Cayman Chemical 21814 L-(?)-α-Methyldopa ≥98% 555-30-6 10g $88 2018-11-19 Buy
Cayman Chemical 21814 L-(?)-α-Methyldopa ≥98% 555-30-6 5g $49 2018-11-19 Buy
Cayman Chemical 21814 L-(?)-α-Methyldopa ≥98% 555-30-6 25g $196 2018-11-19 Buy

Methyldopa Chemical Properties,Uses,Production

Uses

Antihypertensor;L-aromatic aminoacid decarboxylase inhibitor

Uses

vitamin, coenzyme B12

Definition

ChEBI: A derivative of L-tyrosine having a methyl group at the alpha-position and an additional hydroxy group at the 3-position on the phenyl ring.

Biological Functions

The spectrum of activity of α-methyldopa (Aldomet) lies between those of the more potent agents, such as guanethidine, and the milder antihypertensives, such as reserpine. α-Methyldopa is a structural analogue of dihydroxyphenylalanine (dopa) and differs from dopa only by the presence of a methyl group on the -carbon of the side chain.

General Description

Methyldopa differs structurally from L-DOPA only in the presence of a -methyl group. Originally synthesized as an AADC inhibitor,methyldopa ultimately decreases the concentration of DA,NE, E, and serotonin in the CNS and periphery. However,its mechanism of action is not caused by its inhibition ofAADC but, rather, by its metabolism in the CNS to its activemetabolite ( β-methylnorepinephrine). Methyldopa istransported actively into CNS via an aromatic amino acidtransporter, where it is decarboxylated by AADC in thebrain to (1R,2S)- α-methyldopamine. This intermediate, inturn, is stereospecifically β-hydroxylated by DBH to givethe (1R,2S)-α-methylnorepinephrine. This active metaboliteis a selective α2-agonist because it has correct(1R,2S) configuration . It is currently postulated that α-methylnorepinephrine acts on α2-receptors in theCNS in the same manner as clonidine, to decrease sympatheticoutflow and lower blood pressure.

General Description

Colorless or almost colorless crystals or white to yellowish-white fine powder. Almost tasteless. In the sesquihydrate form. pH (saturated aqueous solution) about 5.0.

Air & Water Reactions

Very hygroscopic. Slightly water soluble. May be sensitive to prolonged exposure to air and light. The stability of aqueous solutions is markedly dependent on pH, oxygen and the amount of initial reactant. Aqueous solutions are stable for up to 50 hours in acid and neutral pH (6.2). At pH 8.0, decomposition products are formed in 3 to 5 hours. Solutions develop a red tint that becomes progressively darker (eventually forming a black precipitate).

Reactivity Profile

Methyldopa undergoes catalytic oxygenation in the presence of magnesium, cupric, cobalt, nickel and ferric ions . A weakly acidic amino acid.

Fire Hazard

Flash point data for Methyldopa are not available; however, Methyldopa is probably combustible.

Biological Activity

L-aromatic amino acid decarboxylase inhibitor. Antihypertensive.

Mechanism of action

A number of theories have been put forward to account for the hypotensive action of α-methyldopa. Current evidence suggests that for α-methyldopa to be an antihypertensive agent, it must be converted to α-methylnorepinephrine; however, its site of action appears to be in the brain rather than in the periphery. Systemically administered α-methyldopa rapidly enters the brain, where it accumulates in noradrenergic nerves, is converted to α-methylnorepinephrine, and is released. Released α-methylnorepinephrine activates CNS α- adrenoceptors whose function is to decrease sympathetic outflow. Why α-methylnorepinephrine decreases sympathetic outflow more effectively than does the naturally occurring transmitter is not entirely clear.

Pharmacology

The primary hemodynamic alteration responsible for the hypotensive effects of α-methyldopa remains in dispute. When the patient is supine, the reduction in blood pressure produced by α-methyldopa correlates best with a decrease in peripheral vascular resistance, cardiac output being only slightly reduced. When the patient is upright, the fall in blood pressure corresponds more closely with a reduced cardiac output.
An important aspect of α-methyldopa’s hemodynamic effects is that renal blood flow and glomerular filtration rate are not reduced. As occurs with most sympathetic depressant drugs and vasodilators, long-term therapy with α-methyldopa leads to fluid retention, edema formation, and plasma volume expansion.While data conflict somewhat, it is generally thought that - methyldopa suppresses plasma renin activity.

Clinical Use

α-Methyldopa is not generally believed to be suitable for monotherapy of primary hypertension. Because plasma volume increases as the duration of α-methyldopa therapy is extended, the drug should be used in conjunction with a diuretic; this will produce a significantly greater fall in blood pressure than would occur with either drug used alone. Because α-methyldopa lowers blood pressure without compromising either renal blood flow or the glomerular filtration rate, it is particularly valuable in hypertension complicated by renal disease. However, if end-stage renal failure accompanies severe hypertension,α-methyldopa may not be effective.
The presence of α-methyldopa and its metabolites in the urine reduces the diagnostic value of urinary catecholamine measurements as an indicator of pheochromocytoma, since these substances interfere with the fluorescence assay for catecholamines.

Side effects

The most commonly encountered side effects of α- methyldopa are sedation and drowsiness.These CNS effects are probably the result of reductions in brain catecholamine levels. Other side effects, also typical of sympathetic depression, are dry mouth, nasal congestion, orthostatic hypertension, and impotence.
Autoimmune reactions associated with α-methyldopa treatment include thrombocytopenia and leukopenia. Since a few cases of an α-methyldopa–induced hepatitis have occurred, the drug is contraindicated in patients with active hepatic disease. Flulike symptoms also are known to occur.

Safety Profile

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

Metabolism

Approximately 50% of an orally administered dose of α-methyldopa is absorbed from the gastrointestinal tract. Both peak plasma drug levels and maximal blood pressure–lowering effects are observed 2 to 6 hours after oral administration. A considerable amount of unchanged α-methyldopa and several conjugated and decarboxylated metabolites can be found in the urine.

Purification Methods

Recrystallise methyldopa from H2O. [Reinhold et al. J Org Chem 33 1209 1968.] The L-isomer forms a sesquihydrate from H2O m 302-304o (dec), and the anhydrous crystals are hygroscopic,[] 23D -4.0o (c 1, 0.1N HCl), []546 +154.5o (c 5, CuSO4 solution). It has max at 281nm ( 2780). Its solubility in H2O at 25o is ~10mg/mL and the pH of an aqueous solution is ~5.0. It is insoluble in most organic solvents. [Stein et al. J Am Chem Soc 77 700 1955, Beilstein 4 IV 2505.]

Methyldopa Preparation Products And Raw materials

Raw materials

Preparation Products


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