|Systematic (IUPAC) name|
|(2S)-2-amino- 3-(4-hydroxyphenyl)- 2-methylpropanoic acid|
|(what is this?)|
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.
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). "Α-Methyl α-Amino Acids. II.1Derivatives of DL-Phenylalanine". Journal of the American Chemical Society 77 (3): 700. Bibcode:1955JAChS..77.1678G. 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. doi:10.1021/jo01287a087. PMID 5622474.
- G.A. Stein, I.K. Pfister, U.S. Patent 2,868,818 (1959).
- Green KN, Larsson SK, Beevers DG, Bevan PG, Hayes B (August 1982). "Alpha-methyltyrosine in the management of phaeochromocytoma". Thorax 37 (8): 632–3. doi:10.1136/thx.37.8.632. PMC 459390. PMID 7179194.
- O'Leary OF, Bechtholt AJ, Crowley JJ, Hill TE, Page ME, Lucki I. Depletion of serotonin and catecholamines block the acute behavioral response to different classes of antidepressant drugs in the mouse tail suspension test. Psychopharmacology (Berlin). 2007 Jun;192(3):357-71. PMID 17318507