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Metirosin

ALPHA-METHYL-L-P-TYROSINE Struktur
672-87-7
CAS-Nr.
672-87-7
Bezeichnung:
Metirosin
Englisch Name:
ALPHA-METHYL-L-P-TYROSINE
Synonyma:
METYROSINE;Metirosine;Demser;α-Methyl-L-tyrosine;α-Methyl-L-tyrosine;AMPT;L-AMPT;L-α-MT;α-Me-Tyr-OH;Α-ME-TYR-OH
CBNumber:
CB2480716
Summenformel:
C10H13NO3
Molgewicht:
195.22
MOL-Datei:
672-87-7.mol

Metirosin Eigenschaften

Schmelzpunkt:
320-340°C dec.
Siedepunkt:
383.7±32.0 °C(Predicted)
Dichte
1.283±0.06 g/cm3(Predicted)
storage temp. 
-20°C
L?slichkeit
Aqueous Acid (Slightly)
Aggregatzustand
Powder
pka
pKa 2.7 (Uncertain);10.1 (Uncertain)
Farbe
White to pale yellow
Merck 
13,6183
BRN 
2368400
InChIKey
NHTGHBARYWONDQ-JTQLQIEISA-N
CAS Datenbank
672-87-7(CAS DataBase Reference)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
R-S?tze: 22-38-40-48/20/22
S-S?tze: 22-24/25
WGK Germany  3
TSCA  No
HS Code  2922504500
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P305+P351+P338,P337+P313P
Sicherheit
P261 Einatmen von Staub vermeiden.
P281 Vorgeschriebene pers?nliche Schutzausrüstung verwenden.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach M?glichkeit entfernen. Weiter spülen.

Metirosin Chemische Eigenschaften,Einsatz,Produktion Methoden

S-S?tze Betriebsanweisung:

S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.

Chemische Eigenschaften

White Solid

Verwenden

Metyrosine is the α-methyl derivative of tyrosine. It competitively inhibits tyrosine hydroxylase action, thus reducing the formation of epinephrine and norepinephrine. It is used for treating patients with pheochromocytoma, in cases where a rise in the level of catecholamines is observed.

Verwenden

A tyrosine hydroxylase inhibitor. An antihypertensive in pheochromocytoma

Definition

ChEBI: An L-tyrosine derivative that consists of L-tyrosine bering an additional methyl substituent at position 2. An inhibitor of the enzyme tyrosine 3-monooxygenase, and consequently of the synthesis of catecholamines. It is us d to control the symptoms of excessive sympathetic stimulation in patients with pheochromocytoma.

Allgemeine Beschreibung

Metyrosine (α-Methyl-L-tyrosine, Demser). Althoughinhibition of any of the three enzymes involved in CA biosynthesisshould decrease CAs, inhibitors of the first andthe rate-limiting enzyme TH would be the most effective.As such, metyrosine is a much more effective competitiveinhibitor of E and NE production than agents that inhibitany of the other enzymes involved in CA biosynthesis. Itis often possible to “fool” the enzymes into accepting astructurally similar and unnatural substrate such as metyrosine.Metyrosine differs structurally from tyrosine onlyin the presence of an α-methyl group . It is oneexample of a CA-biosynthesis inhibitor in clinical use.Although metyrosine is used as a racemic mixture, it is the (-)isomer that possesses the inhibitory activity.Metyrosine, which is given orally in dosages ranging from 1 to 4 g/day, is used principally for the preoperative managementof pheochromocytoma, chromaffin cell tumorsthat produce large amounts of NE and E. Although theseadrenal medullary tumors are often benign, patients frequentlysuffer hypertensive episodes. Metyrosine reducesthe frequency and severity of these episodes by significantlylowering CA production (35%–80%). The drug ispolar (log P=0.73) and excreted mainly unchanged in theurine. Because of its limited solubility in water caused byintramolecular bonding of the zwitterions, crystalluria is apotential serious side effect. It can be minimized by maintaininga daily urine volume of more than 2 L. Inhibitors ofCA synthesis have limited clinical utility because suchagents nonspecifically inhibit the formation of all CAs andresult in many side effects. Sedation is the most commonside effect of this drug.
A similar example is the use of α-methyl-m-tyrosine inthe treatment of shock. It differs structurally from metyrosineonly in the presence of m-OH instead of p-OH inmetyrosine. This unnatural amino acid is accepted by the enzymesof the biosynthetic pathway and converted tometaraminol (an α-agonist).

Synthese

Metyrosine, (?)|á-methyltyrosine (12.3.11), is synthesized in a few different ways, the simplest of which is the synthesis from 4-methoxybenzylacetone, which is reacted with potassium cyanide in the presence of ammonium carbonate to give the hydantoin (12.3.9). Treating this with hydrogen iodide removes the methyl-protecting group on the phenyl hydroxyl group and the product (12.3.10) is hydrolyzed by barium hydroxide into a racemic mixture of |á-methyl-D,L-tyrosine, from which the desired L-isomer is isolated (12.3.11) [83¨C86].

Synthesis_672-87-7

Metirosin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Metirosin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 188)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21634 55
career henan chemical co
+86-0371-86658258 +8613203830695
sales@coreychem.com China 29880 58
Hubei xin bonus chemical co. LTD
86-13657291602
linda@hubeijusheng.com CHINA 22963 58
Chongqing Chemdad Co., Ltd
+86-023-6139-8061 +86-86-13650506873
sales@chemdad.com China 39894 58
Shaanxi Dideu Medichem Co. Ltd
+86-29-87569262 +86-15319487004
1015@dideu.com China 3209 58
Guangzhou Yuheng Pharmaceutical Technology Co., Ltd
+8613580539051
joe@yuhengpharm.com CHINA 21142 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000
marketing@targetmol.com United States 32161 58
Hefei TNJ Chemical Industry Co.,Ltd.
+86-0551-65418671 +8618949823763
sales@tnjchem.com China 34563 58
GL Biochem (Shanghai) Ltd.
+86-021-61263370 +86-18901917034
CHINA 3904 58
Shaanxi Dideu Medichem Co. Ltd
+86-029-89586680 +86-18192503167
1026@dideu.com China 7724 58

672-87-7(Metirosin)Verwandte Suche:


  • L-2-METHYL-3-[4-HYDROXYPHENYL]-ALANINE
  • 2-Methyl-L-Tyrosine
  • L-ALPHA-METHYLTYROSINE, 98%
  • AMPT,Metyrosine,
  • -Methyl-L-Tyr
  • A-METHYL-L-TYROSINE
  • L-2-Me-Tyr-OH
  • ALPHA-METHYL-L-P-TRYOSINE
  • (S)-alpha-Methyl-4-hydroxy phenylalanine, (S)-a-Methyltyrosine (>98%, >98%ee)
  • H-alpha-Me-L-Tyr-OH
  • L-2-Methyl-3-(4-hydroxyphenyl)alanine, L-AMPT
  • L-α-Methyltyrosine
  • α-Methyl-L-tyrosine, L-2-Methyl-3-(4-hydroxyphenyl)alanine, L-AMPT
  • (S)-3-(2-Methyl-4-hydroxyphenyl)-2-aminopropionic acid
  • a-Methyl-L-p-tyrosineDiscontinued
  • L-AMPT
  • L-α-Methylrosine
  • Metyrosine (200 mg)
  • L-2-Me-Tyr-OH α-Methyl-L-tyrosine
  • (S)-2-(4-Hydroxybenzyl)-2-aMinopropanoic Acid
  • (S)-α-Methyltyrosine
  • L(-)-Metyrosine
  • L-Metyrosine
  • L-α-Methyl-p-tyrosine
  • L-α-MT
  • (S)-alpha-Methyltyrosine, 98%, 98% ee
  • (S)-alpha-Methyltyrosine, 98% ee, 98%
  • (S)-2-AMINO-2-METHYL-3-(4'-HYDROXYPHENYL)PROPANOIC ACID
  • AMPT
  • ALPHA-METHYLTYROSINE
  • ALPHA-METHYL-L-P-TYROSINE
  • ALPHA-METHYL-L-TYR
  • ALPHA-METHYL-L-TYROSINE
  • A-METHYL-L-P-TYROSINE
  • H-(ME)TYR-OH
  • (S)-a-Methyltyrosine
  • α-Me-Tyr-OH
  • α-Methyl-L-p-tyrosine
  • (S)-α-Methyltyrosine, 98% ee
  • (2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
  • α-Me-L-Tyr-OH
  • Α-ME-TYR-OH
  • Alpha-Methyl-Tyr-OH
  • L-alfa-Me-Tyr-OH
  • L-Tyrosine, α-methyl-
  • ALPHA-METHYL-L-P-TYROSINE USP/EP/BP
  • Metyrosine (Metirosine)
  • α-Methyltyrosine
  • Metyrosine D3
  • L-Tyrosine, a-methyl-
  • Metyrosine (1443205)
  • L-α-Methyltyrosine
  • A-METHYL-L-TYR
  • METYROSINE
  • Metirosine
  • α-Methyl-L-tyrosine
  • Demser
  • α-Methyl-L-tyrosine
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