L-alpha-Methyltyrosine
[CAS# 672-87-7]

Identification

• Classification: Biochemical >> Common amino acids and protein drugs
• Name: L-alpha-Methyltyrosine
• Synonyms: Metyrosine
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.21
• Protein Sequence: X
• CAS Registry Number: 672-87-7
• EC Number: 211-599-5
• SMILES: C[C@](CC1=CC=C(C=C1)O)(C(=O)O)N

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.6, Calc.^*
• Boiling Point: 383.7±32.0 °C (760 mmHg), Calc.^*
• Flash Point: 185.9±25.1 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H335
• Safety Statements: P261-P264-P270-P271-P273-P301+P317-P304+P340-P319-P330-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

L-alpha-Methyltyrosine is an aromatic amino acid derivative with the chemical formula C9H11NO3. It is a structural analog of the amino acid tyrosine, with a methyl group (-CH3) attached to the alpha carbon of the tyrosine backbone. This modification results in a compound that has important biological and pharmacological implications.

L-alpha-Methyltyrosine was first identified as a compound that could inhibit the synthesis of catecholamines, such as dopamine, norepinephrine, and epinephrine. It functions as a competitive inhibitor of the enzyme tyrosine hydroxylase, the rate-limiting enzyme in the biosynthesis of these neurotransmitters. By inhibiting tyrosine hydroxylase, L-alpha-Methyltyrosine reduces the production of catecholamines, which can have significant physiological effects.

Due to its ability to influence catecholamine synthesis, L-alpha-Methyltyrosine has been studied primarily for its potential therapeutic applications in managing certain medical conditions. It has been used experimentally in the treatment of pheochromocytoma, a rare tumor of the adrenal gland that results in excessive secretion of catecholamines. L-alpha-Methyltyrosine, under the trade name metyrosine, is used as part of the treatment regimen to control the overproduction of catecholamines and reduce symptoms such as hypertension, tachycardia, and anxiety, which are commonly associated with the tumor.

In addition to its use in managing pheochromocytoma, L-alpha-Methyltyrosine has been explored in the context of other conditions involving catecholamine dysregulation. For instance, it has been studied as a potential adjunctive treatment for certain psychiatric conditions, such as anxiety disorders or hypertension, where modulation of catecholamine levels might be beneficial. Its role in inhibiting the biosynthesis of catecholamines also makes it a valuable tool for research into the physiological effects of these neurotransmitters.

L-alpha-Methyltyrosine has also been used in laboratory research to study the role of catecholamines in various biological processes. By reducing the levels of neurotransmitters like dopamine and norepinephrine, it helps researchers understand the functions of these molecules in the nervous system and their involvement in conditions such as Parkinson’s disease, schizophrenia, and depression.

Overall, L-alpha-Methyltyrosine, known clinically as metyrosine, is an important compound with applications in the treatment of catecholamine-related disorders. Its ability to inhibit tyrosine hydroxylase makes it a useful tool in both clinical and research settings, particularly for managing conditions such as pheochromocytoma and studying the role of catecholamines in various biological processes.

References

1979. alpha-Methyl-p-tyrosine inhibits the production of free arachidonic acid and diacylglycerols in brain after a single electroconvulsive shock. Neurochemical Research, 4(2).
DOI: 10.1007/bf00964145

1990. Surgical Management of Pheochromocytoma with the Use of Metyrosine. Annals of Surgery, 212(5).
DOI: 10.1097/00000658-199011000-00010

2021. Pheochromocytoma Hypertensive Crisis. Contemporary Endocrinology.
DOI: 10.1007/978-3-030-67455-7_14