Metirosine
Clinical data | |
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Trade names | Demser |
AHFS/Drugs.com | Consumer Drug Information |
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Pharmacokinetic data | |
Elimination half-life | 3.4–3.7 hours |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.010.546 |
Chemical and physical data | |
Formula | C10H13NO3 |
Molar mass | 195.215 g/mol g·mol−1 |
3D model (JSmol) | |
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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.
Clinical use
Metirosine has been used in the treatment of pheochromocytoma.[1] 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.[2]
Chemistry
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.
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instead. - K. Potts, J. Chem. Soc., 1632 (1955).
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instead. - G.A. Stein, I.K. Pfister, U.S. patent 2,868,818 (1959).
See also
References
- ^ 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.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ 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