Metirosine

Metirosine

Clinical data
Trade names	Demser
AHFS/Drugs.com	Consumer Drug Information
ATC code	C02KB01 (WHO)
Pharmacokinetic data
Elimination half-life	3.4–3.7 hours
Identifiers
IUPAC name (2S)-2-amino- 3-(4-hydroxyphenyl)- 2-methylpropanoic acid
CAS Number	672-87-7 Y
PubChem CID	10123
DrugBank	DB00765 Y
ChemSpider	390103 Y
UNII	DOQ0J0TPF7
KEGG	D00762 Y
ChEMBL	ChEMBL1200862 N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C10H13NO3
Molar mass	195.215 g/mol
3D model (JSmol)	Interactive image
SMILES O=C(O)[C@@](N)(Cc1ccc(O)cc1)C
InChI 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 Y Key:NHTGHBARYWONDQ-JTQLQIEISA-N Y
NY (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. 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.

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.