Methyldopa Sesquihydrate

Modify Date: 2024-01-05 16:30:54

Methyldopa Sesquihydrate Structure
Methyldopa Sesquihydrate structure
 Common Name Methyldopa Sesquihydrate
CAS Number 41372-08-1 Molecular Weight 238.24
Density 1.4±0.1 g/cm3 Boiling Point 441.6±45.0 °C at 760 mmHg
Molecular Formula C10H13NO4.3/2H2O Melting Point >300 °C(lit.)
MSDS USA Flash Point 220.9±28.7 °C

 Use of Methyldopa Sesquihydrate


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.

 Names

Name L-α-Methyl DOPA Hydrate
Synonym More Synonyms

 Methyldopa Sesquihydrate 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
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.

 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 C10H13NO4.3/2H2O
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

 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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 Synonyms

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)
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