Metirosine

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Metirosine
Clinical data
Trade namesDemser
AHFS/Drugs.comConsumer Drug Information
ATC code
Pharmacokinetic data
Elimination half-life3.4–3.7 hours
Identifiers
  • (2S)-2-amino- 3-(4-hydroxyphenyl)- 2-methylpropanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.010.546 Edit this at Wikidata
Chemical and physical data
FormulaC10H13NO3
Molar mass195.215 g/mol g·mol−1
3D model (JSmol)
  • O=C(O)[C@@](N)(Cc1ccc(O)cc1)C
  • InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1 checkY
  • Key:NHTGHBARYWONDQ-JTQLQIEISA-N checkY
 ☒NcheckY (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.

  • Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/ja01608a046, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/ja01608a046 instead.
  • K. Potts, J. Chem. Soc., 1632 (1955).
  • Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/jo01287a087, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/jo01287a087 instead.
  • 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. doi:10.1136/thx.37.8.632. PMC 459390. PMID 7179194.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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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