Methyldopa Sesquihydrate

Names

[ Name ]:
Methyldopa Sesquihydrate

[Synonym ]:
a-Methyl-L-dopa
α-Methyl-L-dopa
Dopegyt
L-(-)-b-(3,4-Dihydroxyphenyl)-a-methylalanine
L-(-)-α-Methyl-β-(3,4-dihydroxyphenyl)alanine
L-(-)-a-Methyl-b-(3,4-dihydroxyphenyl)alanine
a-Methyl Dopa
L-α-Methyl-DOPA
α-Methyl dopa
EINECS 209-089-2
L-Tyrosine, 3-hydroxy-α-methyl-, hydrate (2:3)
Tyrosine, 3-hydroxy-α-methyl-, hydrate (1:1)
L-(a-Md)
L-α-Methyldopa
α-Methyldopa sesquihydrate
(-)-α-Methyldopa
3-Hydroxy-α-methyl-L-tyrosine
L-Tyrosine, 3-hydroxy-α-methyl-
Dopamet
(−)-3-(3,4-Dihydroxyphenyl)-2-methyl-L-alanine sesquihydrate
3-(3,4-Dihydroxyphenyl)-2-methyl-L-alanine,MK-351,Methyl-L-DOPA
(S)-(-)-a-Methyldopa
a-Methyl-b-(3,4-dihydroxyphenyl)-L-alanine
Bayer 1440L
Methyl dopa
Aldomet
(-)-3-(3,4-Dihydroxyphenyl)-2-Methyl-L-Alanine Sesquihydrate
l-a-Methyldopa
(S)-a-Methyldopa
ALDORIL
Alpha-Methyldopa Sesquihydrate
Alanine, 3- (3,4-dihydroxyphenyl)-2-methyl-, L-
MFCD00149280
Methyldopa
3-Hydroxy-α-methyltyrosine hydrate (1:1)
L-a-Methyl-3,4-dihydroxyphenylalanine
(-)-Methyldopa
Elanpres
L-Methyldopa
L-(-)-α-Methyldopa (hydrate)

Biological Activity

[Description]:

L-(-)-α-Methyldopa hydrate is an alpha-adrenergic agonist (selective for α2-adrenergic receptors) psychoactive drug used as a sympatholytic or antihypertensive.Target: alpha-adrenergic agonistMethyldopa is an alpha-adrenergic agonist (selective for α2-adrenergic receptors) psychoactive drug used as a sympatholytic or antihypertensive. Its use is now mostly deprecated following the introduction of alternative safer classes of agents. However, it continues to have a role in otherwise difficult to treat hypertension and gestational hypertension (also known as pregnancy-induced hypertension (PIH)).Methyldopa has a dual mechanism of action. It is a competitive inhibitor of the enzyme DOPA decarboxylase, also known as aromatic L-amino acid decarboxylase, which converts L-DOPA into dopamine. Dopamine is a precursor for norepinephrine (noradrenaline) and subsequently epinephrine (adrenaline). This inhibition results in reduced dopaminergic and adrenergic neurotransmission in the peripheral nervous system. This effect may lower blood pressure and cause central nervous system effects such as depression, anxiety, apathy, anhedonia, and parkinsonism. It is converted to α-methylnorepinephrine by dopamine beta-hydroxylase (DBH). α-methylnorepinephrine is an agonist of presynaptic central nervous system α2-adrenergic receptors. Activation of these receptors in the brainstem appears to inhibit sympathetic nervous system output and lower blood pressure. This is also the mechanism of action of clonidine.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor

Research Areas >> Cardiovascular Disease

[References]

[1]. BAILA MR, et al. The use of the combination of L-alpha-methyldopa and dichlorothiazide in the treatment of arterial hypertension. Dia Med. 1962 Dec 6;34:2422-4.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
441.6±45.0 °C at 760 mmHg

[ Melting Point ]:
>300 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₃NO_4.3/₂H₂O

[ Molecular Weight ]:
238.24

[ Flash Point ]:
220.9±28.7 °C

[ PSA ]:
113.01000

[ LogP ]:
0.13

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.635

[ Storage condition ]:
Refrigerator

[ Stability ]:
Stable, but may be light sensitive. Very hygroscopic. Undergoes catalytic oxygenation in the presence of magnesium, cupric, cobalt, nickel and ferric ions. Store under a dry atmosphere.

[ Water Solubility ]:
0.1-1 g/100 mL at 23 ºC

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YP2860000

CHEMICAL NAME :: L-Tyrosine, 3-hydroxy-alpha-methyl-, sesquihydrate

CAS REGISTRY NUMBER :: 41372-08-1

LAST UPDATED :: 199707

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C10-H13-N-O4.3/2H2-O

MOLECULAR WEIGHT :: 238.27

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 17500 mg/kg/14D-C

TOXIC EFFECTS :: Related to Chronic Data - death

REFERENCE :: NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-348,1989

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 68250 mg/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight Kidney, Ureter, Bladder - other changes

REFERENCE :: NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-348,1989 ** TUMORIGENIC DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 604 gm/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Kidney, Ureter, Bladder - Kidney tumors

REFERENCE :: NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-348,1989 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2980 mg/kg

SEX/DURATION :: male 65 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - other effects on male Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

REFERENCE :: NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-348,1989

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Risk Phrases ]:
R20/21:Harmful by inhalation and in contact with skin . R36/37/38:Irritating to eyes, respiratory system and skin . R42/43:May cause sensitization by inhalation and skin contact . R65:Harmful: May cause lung damage if swallowed.

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
YP2860000

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