Metirosine

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Metirosine
File:Metirosine.svg
Systematic (IUPAC) name
(2S)-2-amino- 3-(4-hydroxyphenyl)- 2-methylpropanoic acid
Clinical data
Trade names Demser
AHFS/Drugs.com Consumer Drug Information
Legal status ?
Pharmacokinetic data
Half-life 3.4–3.7 hours
Identifiers
CAS number 672-87-7 7pxY
ATC code C02KB01
PubChem CID 10123
DrugBank DB00765
ChemSpider 390103 7pxY
UNII DOQ0J0TPF7 7pxY
KEGG D00762 7pxY
ChEMBL CHEMBL1200862 7pxN
Chemical data
Formula C10H13NO3 
Mol. mass 195.215 g/mol
 14pxN (what is this?)  (verify)

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. 500px

  • Stein, G. A.; Bronner, H. A.; Pfister, K. (1955). Journal of the American Chemical Society 77 (3): 700. doi:10.1021/ja01608a046.  edit
  • 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.  edit
  • G.A. Stein, I.K. Pfister, U.S. Patent 2,868,818 (1959).

See also

References

  1. Green KN, Larsson SK, Beevers DG, Bevan PG, Hayes B (August 1982). "Alpha-methyltyrosine in the management of phaeochromocytoma". Thorax 37 (8): 632–3. PMC 459390. PMID 7179194. doi:10.1136/thx.37.8.632. 
  2. 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


      
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