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620-30-4 molecular structure
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(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid

ChemBase ID: 645
Molecular Formular: C10H13NO3
Molecular Mass: 195.21512
Monoisotopic Mass: 195.08954328
SMILES and InChIs

SMILES:
OC(=O)C(N)(Cc1ccc(O)cc1)C
Canonical SMILES:
Oc1ccc(cc1)CC(C(=O)O)(N)C
InChI:
InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1
InChIKey:
NHTGHBARYWONDQ-JTQLQIEISA-N

Cite this record

CBID:645 http://www.chembase.cn/molecule-645.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
IUPAC Traditional name
metyrosine
AMPT
Brand Name
Demser
Synonyms
Metirosine
Methyltyrosine
Metyrosine
L-2-Methyl-3-(4-hydroxy-phenyl)alanine
α-Methyl-L-tyrosine
DL-2-Methyl-3-(4-hydroxyphenyl)alanine
L-AMPT
α-Methyl-L-tyrosine
L-2-Methyl-3-(4-hydroxyphenyl)alanine
L-α-Methyltyrosine
AMPT
α-Methyl-DL-tyrosine
(+/-)-α-Methyl-p-tyrosine
Racemetirosine
α-Methyltyrosine
α-Methyl-D,L-tyrosine
α-甲基-L-酪氨酸
α-甲基-L-酪氨酸
L-2-甲基-3-(4-羟基苯基)丙氨酸
L-α-甲基酪氨酸
DL-2-甲基-3-(4-羟基苯基)丙氨酸
α-甲基-DL-酪氨酸
CAS Number
620-30-4
672-87-7
658-48-0
EC Number
211-523-0
211-599-5
MDL Number
MFCD00004187
MFCD00064201
Beilstein Number
2368400
2938704
PubChem SID
46506079
24885951
24278151
160964108
24278155
PubChem CID
441350

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 2.0631347  H Acceptors
H Donor LogD (pH = 5.5) -1.0558071 
LogD (pH = 7.4) -1.0610021  Log P -1.0558642 
Molar Refractivity 51.8105 cm3 Polarizability 20.34689 Å3
Polar Surface Area 83.55 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -1.91  LOG S -1.9 
Solubility (Water) 2.48e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Aqueous Sodium Hydroxide expand Show data source
Very slightly soluble expand Show data source
Water expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
>280°C (dec.) expand Show data source
>300 °C(lit.) expand Show data source
Optical Rotation
[α]20/D -7°, c = 1 in 0.1 M HCl expand Show data source
Hydrophobicity(logP)
-1.7 expand Show data source
Storage Condition
Refrigerator expand Show data source
RTECS
YP2890000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
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German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... TH(7054) expand Show data source
Purity
≥95% (NT) expand Show data source
≥98% (TLC) expand Show data source
≥99.0% (TLC) expand Show data source
98% expand Show data source
Certificate of Analysis
Download expand Show data source
Ignition Residue
≤0.05% expand Show data source
Linear Formula
4-(HO)C6H4CH2C(CH3)(NH2)CO2H expand Show data source
Empirical Formula (Hill Notation)
C10H13NO3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00765 external link
Item Information
Drug Groups approved
Description An inhibitor of the enzyme tyrosine 3-monooxygenase, and consequently of the synthesis of catecholamines. It is used to control the symptoms of excessive sympathetic stimulation in patients with pheochromocytoma. (Martindale, The Extra Pharmacopoeia, 30th ed)
Indication For use in the treatment of patients with pheochromocytoma, for preoperative preparation of patients for surgery, management of patients when surgery is contraindicated, and chronic treatment of patients with malignant pheochromocytoma.
Pharmacology In patients with pheochromocytoma, who produce excessive amounts of norepinephrine and epinephrine, administration of one to four grams of metyrosine per day has reduced catecholamine biosynthesis from about 35 to 80 percent as measured by the total excretion of catecholamines and their metabolites (metanephrine and vanillylmandelic acid). The maximum biochemical effect usually occurs within two to three days, and the urinary concentration of catecholamines and their metabolites usually returns to pretreatment levels within three to four days after metyrosine is discontinued. Most patients with pheochromocytoma treated with metyrosine experience decreased frequency and severity of hypertensive attacks with their associated headache, nausea, sweating, and tachycardia. In patients who respond, blood pressure decreases progressively during the first two days of therapy with metyrosine; after withdrawal, blood pressure usually increases gradually to pretreatment values within two to three days.
Toxicity Signs of metyrosine overdosage include those central nervous system effects observed in some patients even at low dosages. At doses exceeding 2000 mg/day, some degree of sedation or feeling of fatigue may persist. Doses of 2000-4000 mg/day can result in anxiety or agitated depression, neuromuscular effects (including fine tremor of the hands, gross tremor of the trunk, tightening of the jaw with trismus), diarrhea, and decreased salivation with dry mouth. The acute toxicity of metyrosine was 442 mg/kg and 752 mg/kg in the female mouse and rat respectively.
Affected Organisms
Humans and other mammals
Biotransformation Little biotransformation, with catechol metabolites accounting for less than 1% of the administered dose.
Absorption Well absorbed from the gastrointestinal tract.
Half Life 3.4 to 3.7 hours
Elimination Because the first step is also the rate-limiting step, blockade of tyrosine hydroxylase activity results in decreased endogenous levels of catecholamines, usually measured as decreased urinary excretion of catecholamines and their metabolites.
External Links
RxList
Drugs.com
Sigma Aldrich - M7628 external link
Biochem/physiol Actions
酪氨酸羟化酶抑制剂。
Sigma Aldrich - M8131 external link
Biochem/physiol Actions
Tyrosine hydroxylase inhibitor.
Other Notes
Active isomer
Packaging
1, 5 g in poly bottle
100, 250 mg in poly bottle
Sigma Aldrich - 120693 external link
Biochem/physiol Actions
Tyrosine hydroxylase inhibitor.
Packaging
5, 25 g in glass bottle
Sigma Aldrich - 69577 external link
Biochem/physiol Actions
Tyrosine hydroxylase inhibitor.
Other Notes
Inhibitor (Ki 5 uM) of tyrosine hydroxylase1
Sigma Aldrich - 69574 external link
Biochem/physiol Actions
Tyrosine hydroxylase inhibitor.
Toronto Research Chemicals - M332685 external link
A tyrosine hydroxylase inhibitor. An antihypertensive in pheochromocytoma.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Gilbert, J.A., et al.: Biochem. Pharmacol., 69, 1159 (2005)
  • • Morimoto, E., et al.: J. Pharmacol. Sci., 108, 505 (2005)
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PATENTS

PATENTS

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