α-Methyl-p-tyrosine

α-Methyl-p-tyrosine
Identifiers
	Compounds; 2S: Metirosine; 2R: (Inactive isomer); 2RS: α-Methyl-p-tyrosine;
CAS Number	2S: 672-87-7 ; 2R: 672-86-6 ; 2RS: 658-48-0 ;
3D model (JSmol)	2S: Interactive image;
ChEMBL	2S: ChEMBL1200862 ;
ChemSpider	2S: 390103 ; 2R: 12129 ; 2RS: 3013 ;
DrugBank	2S: DB00765 ;
ECHA InfoCard	100.010.477
IUPHAR/BPS	2S: 6956;
KEGG	2S: D00762 ;
PubChem CID	2S: 441350; 2R: 12650; 2RS: 3125;
UNII	2S: DOQ0J0TPF7 ;
CompTox Dashboard (EPA)	2S: DTXSID90859529 ;
	InChI 2S: 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 Key: NHTGHBARYWONDQ-JTQLQIEISA-N; 2R: 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-/m1/s1 Key: NHTGHBARYWONDQ-SNVBAGLBSA-N; 2RS: 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) Key: NHTGHBARYWONDQ-UHFFFAOYSA-N;
	SMILES 2S: C[C@](Cc1ccc(cc1)O)(C(=O)O)N;
Properties
Chemical formula	C10H13NO3
Molar mass	195.218 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

α-Methyl-p-tyrosine (AMPT), or simply α-methyltyrosine, also known in its chiral 2-(S) form as metirosine, is a tyrosine hydroxylase enzyme inhibitor and is therefore a drug involved in inhibiting the catecholamine biosynthetic pathway.^[1] AMPT inhibits tyrosine hydroxylase whose enzymatic activity is normally regulated through the phosphorylation of different serine residues in regulatory domain sites.^[1] Catecholamine biosynthesis starts with dietary tyrosine, which is hydroxylated by tyrosine hydroxylase and it is hypothesized that AMPT competes with tyrosine at the tyrosine-binding site, causing inhibition of tyrosine hydroxylase.^[2]

It has been used in the treatment of pheochromocytoma.^[2] It has been demonstrated to inhibit the production of melanin.^[3] It is available as a generic medication.^[4]

^ ^a ^b Nestler EJ, Hyman SE, Malenka RC (2008). Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (Second ed.). McGraw Hill Professional. ISBN 9780071641197.
^ ^a ^b Ankenman R, Salvatore MF (2007). "Low dose alpha-methyl-para-tyrosine (AMPT) in the treatment of dystonia and dyskinesia". The Journal of Neuropsychiatry and Clinical Neurosciences. 19 (1): 65–69. doi:10.1176/jnp.2007.19.1.65. PMID 17308229.
^ US 6359001, Drago F, "Use of α-methyl-p-tyrosine to inhibit melanin production in iris melanocytes", issued 19 March 2002, assigned to Pfizer Health AB.
^ "Metyrosine: FDA-Approved Drugs". U.S. Food and Drug Administration. Archived from the original on October 20, 2020. Retrieved 15 August 2020.

[nestler-1] Nestler EJ, Hyman SE, Malenka RC (2008). Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (Second ed.). McGraw Hill Professional. ISBN 9780071641197.

[Ankenman_2007-2] Ankenman R, Salvatore MF (2007). "Low dose alpha-methyl-para-tyrosine (AMPT) in the treatment of dystonia and dyskinesia". The Journal of Neuropsychiatry and Clinical Neurosciences. 19 (1): 65–69. doi:10.1176/jnp.2007.19.1.65. PMID 17308229.

[3] US 6359001, Drago F, "Use of α-methyl-p-tyrosine to inhibit melanin production in iris melanocytes", issued 19 March 2002, assigned to Pfizer Health AB.

[4] "Metyrosine: FDA-Approved Drugs". U.S. Food and Drug Administration. Archived from the original on October 20, 2020. Retrieved 15 August 2020.

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