CAS No.555-30-6,Methyldopa Suppliers

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Basic Information

Molecular Structure:
CAS No.:	555-30-6
Name:	Methyldopa
Article Data:	14

Formula:	C₁₀H₁₃NO₄
Molecular Weight:	211.218
Synonyms:	Alanine,3-(3,4-dihydroxyphenyl)-2-methyl-, L- (8CI);(-)-Methyldopa;(S)-(-)-a-Methyldopa;2-Methyl-3-(3,4-dihydroxyphenyl)alanine;Aldometil;Alphamethyldopa;Baypresol;Dopatec;Equibar;L-(-)-a-Methyl-b-(3,4-dihydroxyphenyl)alanine;L-3,4-Dihydroxy-a-methylphenylalanine;Levo-3-(3,4-Dihydroxyphenyl)-2-methylalanine;Medomet;Medopa;Methoplain;Methyldopa;NSC 169916;Presinol;Presolisin;
EINECS:	209-089-2
Density:	1.403 g/cm³
Melting Point:	300 °C
Boiling Point:	441.6 °C at 760 mmHg
Flash Point:	220.9 °C
Solubility:	10g/L(temperature not stated)
Appearance:	Colorless or almost colorless crystals or white to yellowish-white fine powder
PSA:	103.78000
LogP:	1.14260

Synthetic route

: (S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid hydrochloride

: 555-30-6
methyldopa

Conditions

Conditions	Yield
With methyloxirane In ethanol for 3h; Inert atmosphere; Reflux;	86%

: 16825-27-7
(S)-N-Acetyl-α-methyl-β-(3,4-dimethoxyphenyl)alanin

: 555-30-6
methyldopa

Conditions

Conditions	Yield
With hydrogen bromide Heating;

: 39948-18-0
(S)-3-(3,4-dimethoxyphenyl)-2-methylalanine

: 555-30-6
methyldopa

Conditions

Conditions	Yield
With hydrogen bromide

: 109522-07-8
(2S)-2-amino-2-methyl-3-(3,4-dimethoxyphenyl)propanamide

: 555-30-6
methyldopa

Conditions

Conditions	Yield
With hydrogen bromide

: 121704-32-3
N-Chloroacetyl-α-methyl-DOPA

A: 555-30-6
methyldopa

B: 61406-34-6, 121704-32-3
N-Chloroacetyl-D-α-methyl-DOPA

Conditions

Conditions	Yield
With potassium hydroxide; potassium phosphate buffer; porcine kidney acylase I at 40℃; relative initial rate of hydrolysis, also with Aspergillus acylase I as a catalyst; with or without CoCl2;

: 98262-54-5
(2S,5S)-1-benzoyl-2-(tert-butyl)-5-(3',4'-dimethoxybenzyl)-3,5-dimethylimidazolidin-4-one

: 555-30-6
methyldopa

Conditions

Conditions	Yield
With hydrogenchloride at 175 - 185℃; for 4h;

: 21852-32-4
4-bromomethyl-1,2-dimethoxybenzene

: 555-30-6
methyldopa

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran; hexane / 2 h / -78 - 0 °C 2: aq. 6N HCl / 4 h / 175 - 185 °C View Scheme
Multi-step reaction with 4 steps 1: NaH / tetrahydrofuran / 0 - 25 °C 2: α-chymotrypsin / dimethylsulfoxide; H2O / 22 - 25 °C / potassium phosphate ( pH 7.0); with pig liver esterase the reaction rate is higher but the e.e. is lower 3: 1.) acyl azide formation, 2.) Curtius rearrangement 4: aq. HBr (48percent) View Scheme

: 33859-00-6
benzyl-veratryliden-amine

: 555-30-6
methyldopa

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / 1.) NEt3 / CH2Cl2 / 1.) -78 deg C; 2.) -78-0 deg C 2: 90 percent / 1.) LiHMDS 3: 90 percent / Li/NH3 / tetrahydrofuran; 2-methyl-propan-2-ol 4: aq. HBr View Scheme

: 111793-95-4
(3S,4R)-1-benzyl-3-<2-oxo-4(S)-phenyloxazolidinyl>-4-(3,4-dimethoxyphenyl)azetidin-2-one

: 555-30-6
methyldopa

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / 1.) LiHMDS 2: 90 percent / Li/NH3 / tetrahydrofuran; 2-methyl-propan-2-ol 3: aq. HBr View Scheme

: 111793-96-5
(3S,4R)-1-benzyl-3-methyl-3-<2-oxo-(4S)-phenyloxazolidinyl>-4-(3,4-dimethoxyphenyl)azetidin-2-one

: 555-30-6
methyldopa

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / Li/NH3 / tetrahydrofuran; 2-methyl-propan-2-ol 2: aq. HBr View Scheme

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History

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.

Specification

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:

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)	CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	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)	PERIPHERAL NERVE AND SENSATION: FASCICULATIONS BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: TREMOR	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.