Methyldopa

Modify Date: 2024-01-02 12:49:46

Methyldopa Structure
Methyldopa structure
 Common Name Methyldopa
CAS Number 555-30-6 Molecular Weight 211.214
Density 1.4±0.1 g/cm3 Boiling Point 441.6±45.0 °C at 760 mmHg
Molecular Formula C10H13NO4 Melting Point ≥300 °C
MSDS N/A Flash Point 220.9±28.7 °C

 Use of Methyldopa


Methyldopa 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 α-methyl-L-dopa
Synonym More Synonyms

 Methyldopa Biological Activity

Description Methyldopa 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
Molecular Formula C10H13NO4
Molecular Weight 211.214
Flash Point 220.9±28.7 °C
Exact Mass 211.084457
PSA 103.78000
LogP 0.13
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.635
Storage condition Store at RT

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AY5950000
CHEMICAL NAME :
Alanine, 3-(3,4-dihydroxyphenyl)-2-methyl-, L-(-)-
CAS REGISTRY NUMBER :
555-30-6
LAST UPDATED :
199707
DATA ITEMS CITED :
32
MOLECULAR FORMULA :
C10-H13-N-O4
MOLECULAR WEIGHT :
211.24
WISWESSER LINE NOTATION :
QVXZ1&1R CQ DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
900 mg/kg/13W-I
TOXIC EFFECTS :
Behavioral - tremor
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1830 mg/kg/17W-I
TOXIC EFFECTS :
Peripheral Nerve and Sensation - fasciculations Behavioral - hallucinations, distorted perceptions Behavioral - tremor
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1071 mg/kg/22W-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, allergic (after systemic exposure)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
44 gm/kg/3Y-I
TOXIC EFFECTS :
Gastrointestinal - necrotic changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP Vascular - BP lowering not characterized in autonomic section
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1700 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
713 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
713 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
56875 mg/kg/13W-C
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - changes in bone marrow (not otherwise specified) Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
136 gm/kg/13W-C
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
12105 mg/kg/50D-I
TOXIC EFFECTS :
Endocrine - changes in spleen weight Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in leukocyte (WBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
10950 mg/kg
SEX/DURATION :
female 2 year(s) pre-mating female 1-12 week(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders Reproductive - Maternal Effects - breasts, lactation (prior to or during pregnancy)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
1680 mg/kg
SEX/DURATION :
female 28-36 week(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - other neonatal measures or effects Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - biochemical and metabolic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
2306 mg/kg
SEX/DURATION :
female 5-14 week(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2100 mg/kg
SEX/DURATION :
female 1-21 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
7500 mg/kg
SEX/DURATION :
female 6-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
7500 mg/kg
SEX/DURATION :
female 6-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
13 gm/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 - testes, epididymis, sperm duct Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
300 mg/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
480 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
960 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
80 mg/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
150 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - other effects on male
TYPE OF TEST :
Dominant lethal test

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
37 mg/L
REFERENCE :
GMCRDC Gann Monograph on Cancer Research. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No. 11- 1971- Volume(issue)/page/year: 27,95,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3201 No. of Facilities: 366 (estimated) No. of Industries: 2 No. of Occupations: 13 No. of Employees: 16478 (estimated) No. of Female Employees: 11629 (estimated)

 Safety Information

Safety Phrases S24/25
WGK Germany 3
RTECS YP2860000
HS Code 2918199090

 Customs

HS Code 2918199090
Summary 2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

 Synonyms

a-Methyl-L-dopa
α-Methyl-L-dopa
Methyldopa Sesquihydrate
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
alpha-methyl-L-dopa
MFCD00004186
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-
Methyldopa
3-Hydroxy-α-methyltyrosine hydrate (1:1)
L-a-Methyl-3,4-dihydroxyphenylalanine
(-)-Methyldopa
Elanpres
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Related Compounds: More...
Methyldopa
41372-08-1
Methyldopa
55-40-3
Methyldopa
555-29-3
Methyldopate
6014-30-8
N-Methyldopa
70152-53-3
D-Methyldopa
2799-15-7
3-O-methyldopa
300-48-1
3-O-Methyldopa
7636-26-2
3-O-Methyldopa
4214-13-5
Chemsrc provides Methyldopa(CAS#:555-30-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Methyldopa are included as well.>> amp version: Methyldopa

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