Metirosine (INN and BAN; α-Methyltyrosine, Metyrosine USAN, AMPT) is an antihypertensive drug. It inhibits the enzyme tyrosine hydroxylase and, therefore, catecholamine synthesis, which, as a consequence, depletes the levels of the catecholamines dopamine, adrenaline and noradrenaline in the body.
Metirosine has been used in the treatment of pheochromocytoma. It is contra-indicated for the treatment of essential hypertension.
However it is now rarely used in medicine, its primary use being in scientific research to investigate the effects of catecholamine depletion on behaviour.
Metyrosine, (−)α-methyltyrosine, is synthesized in a few different ways, the simplest of which is the synthesis from 4-methoxyphenylacetone, which is reacted with potassium cyanide in the presence of ammonium carbonate to give the hydantoin. Treating this with hydrogen iodide removes the methyl-protecting group on the phenyl hydroxyl group and the product is hydrolyzed by barium hydroxide into a racemic mixture of α-methyl-D,L-tyrosine, from which the desired L-isomer is isolated.
- Stein, G. A.; Bronner, H. A.; Pfister, K. (1955). Journal of the American Chemical Society 77 (3): 700. doi:10.1021/ja01608a046.
- K. Potts, J. Chem. Soc., 1632 (1955).
- Saari, W. S. (1967). "Reaction of nitro anions with N,N-dimethyl-p-hydroxybenzylamine. A new synthesis of alpha-methyltyrosine". Journal of Organic Chemistry 32 (12): 4074–4076. PMID 5622474. doi:10.1021/jo01287a087.
- G.A. Stein, I.K. Pfister, U.S. Patent 2,868,818 (1959).
- Adamantanes: Amantadine
- Rimantadine; Aminotetralins: 7-OH-DPAT
- UH-232; Benzazepines: 6-Br-APB
- SKF-83,959; Ergolines: Bromocriptine
- Pergolide; Dihydrexidine derivatives: 2-OH-NPA
- Doxanthrine; Others: A-68,930
- Salvinorin A