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658-48-0 分子结构
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(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid

ChemBase编号:645
分子式:C10H13NO3
平均质量:195.21512
单一同位素质量:195.08954328
SMILES和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

引用这个纪录

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

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
IUPAC传统名
metyrosine
AMPT
商标名
Demser
别名
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
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
CAS号
658-48-0
672-87-7
620-30-4
EC号
211-599-5
211-523-0
MDL号
MFCD00064201
MFCD00004187
Beilstein号
2368400
2938704
PubChem SID
24278151
46506079
160964108
24885951
24278155
PubChem CID
441350

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 2.0631347  质子受体
质子供体 LogD (pH = 5.5) -1.0558071 
LogD (pH = 7.4) -1.0610021  Log P -1.0558642 
摩尔折射率 51.8105 cm3 极化性 20.34689 Å3
极化表面积 83.55 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -1.91  LOG S -1.9 
溶解度 2.48e+00 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
Aqueous Sodium Hydroxide expand 查看数据来源
Very slightly soluble expand 查看数据来源
Water expand 查看数据来源
外观
White to Off-White Solid expand 查看数据来源
熔点
>280°C (dec.) expand 查看数据来源
>300 °C(lit.) expand 查看数据来源
比旋光度
[α]20/D -7°, c = 1 in 0.1 M HCl expand 查看数据来源
疏水性(logP)
-1.7 expand 查看数据来源
保存条件
Refrigerator expand 查看数据来源
RTECS编号
YP2890000 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand 查看数据来源
保存温度
-20°C expand 查看数据来源
相关基因信息
human ... TH(7054) expand 查看数据来源
纯度
≥95% (NT) expand 查看数据来源
≥98% (TLC) expand 查看数据来源
≥99.0% (TLC) expand 查看数据来源
98% expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
燃烧残渣
≤0.05% expand 查看数据来源
线性分子式
4-(HO)C6H4CH2C(CH3)(NH2)CO2H expand 查看数据来源
Empirical Formula (Hill Notation)
C10H13NO3 expand 查看数据来源

详细说明

详细说明

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
包装
1, 5 g in poly bottle
100, 250 mg in poly bottle
Sigma Aldrich -  120693 external link
Biochem/physiol Actions
酪氨酸羟化酶抑制剂。
包装
5, 25 g in glass bottle
Sigma Aldrich -  69577 external link
Biochem/physiol Actions
酪氨酸羟化酶抑制剂。
Other Notes
酪氨酸羟化酶抑制剂 (Ki 5uM)1
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.

参考文献

参考文献

供应商提供 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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专利

专利

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