ALPHA-METHYL-L-P-TYROSINE

한글명:ALPHA-METHYL-L-P-TYROSINE

카스 번호672-87-7

상품명:ALPHA-METHYL-L-P-TYROSINE

CBNumberCB2480716

분자식C10H13NO3

포뮬러 무게195.22

MOL 파일672-87-7.mol

화학적 성질

녹는점	320-340°C dec.
끓는 점	383.7±32.0 °C(Predicted)
밀도	1.283±0.06 g/cm3(Predicted)
저장 조건	-20°C
용해도	산성 용액(약간 용해됨)
물리적 상태	가루
산도 계수 (pKa)	pKa 2.7 (Uncertain);10.1 (Uncertain)
색상	흰색에서 연한 노란색
Merck	13,6183
BRN	2368400
InChIKey	NHTGHBARYWONDQ-JTQLQIEISA-N
CAS 데이터베이스	672-87-7(CAS DataBase Reference)

위험 및 안전 성명

위험 카페고리 넘버

22-38-40-48/20/22

안전지침서

22-24/25

WGK 독일

TSCA

HS 번호

2922504500

NFPA 704:

	0
2		0

그림문자(GHS)

ALPHA-METHYL-L-P-TYROSINE 화학적 특성, 용도, 생산

화학적 성질
White Solid
용도
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.
용도
A tyrosine hydroxylase inhibitor. An antihypertensive in pheochromocytoma
정의
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.
일반 설명
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).
Synthesis
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].

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