Compound: METYROSINE
SMILES: O=C(O)[C@@](N)(Cc1ccc(O)cc1)C
InChIKey: NHTGHBARYWONDQ-JTQLQIEISA-N
Synonyms: METYROSINE, 672-87-7, Metirosine, Demser, Metirosina, (2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid, (S)-alpha-Methyltyrosine, L-alpha-Methyltyrosine, Metirosinum, (-)-alpha-Methyl-L-tyrosine, Alpha-Methyl-L-P-Tyrosine, MK-781, DOQ0J0TPF7, CHEBI:6912, DTXSID6023315, L-588357-0, DTXCID203315, methyl-tyrosine, RefChem:56543, alpha-Methyltyrosine, (L)-, C02KB01, 211-599-5, alpha-Methyl-L-tyrosine, Methyltyrosine, (S)-2-Amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid, L-alpha-Methyl-p-tyrosine, MFCD00064201, Metirosine [INN], (S)-2-(4-Hydroxybenzyl)-2-aminopropanoic Acid, L-Tyrosine, alpha-methyl-, (-)-, NCGC00094144-03, (2S)-2-amino-3-(4-hydroxyphenyl)-2-methyl-propanoic acid, CAS-672-87-7, Metyrosine [USAN], alpha-methyl-paratyrosine, Metyrosine [USAN:USP], Metirosinum [INN-Latin], UNII-DOQ0J0TPF7, MK 781, Metirosina [INN-Spanish], L-Tyrosine, .alpha.-methyl-, L-Methyltyrosine, Metyrosine (USP), EINECS 211-599-5, Demser (TN), a-Me-Tyr-OH, ?-Methyl-L-tyrosine, Metyrosine (Standard), |_-Methyl-L-tyrosine, Racemetirosine, (s)-, METYROSINE [MI], Metirosine (JAN/INN), METIROSINE [JAN], Spectrum3_001846, METYROSINE [VANDF], Epitope ID:768772, H-(ME)TYR-OH, L-Tyrosine, alpha-methyl-, A-METHYL-L-TYROSINE, L-2-METHYL-3-(4-HYDROXYPHENYL)ALANINE, METIROSINE [MART.], METIROSINE [WHO-DD], METYROSINE [USP-RS], Lopac0_000811, SCHEMBL50398, BSPBio_003232, SPECTRUM2300312, GTPL6956, L 588357-0, orb1305970, CHEMBL1200862, METYROSINE [ORANGE BOOK], KBio3_002732, (-)-(S)-2-Amino-3-(4-hydroxyphenyl)-2-methylpropionsaeure, HMS3262D03, METYROSINE [USP MONOGRAPH], HY-W015007R, .alpha.-Methyl-L-tyrosine (NIST), Tox21_111253, Tox21_500811, EBC-12576, AKOS016844271, Tox21_111253_1, AB02561, CCG-204895, CS-W015723, DB00765, FM72860, HY-W015007, LP00811, SDCCGSBI-0050788.P002, (-)-.ALPHA.-METHYL-L-TYROSINE, NCGC00015701-06, NCGC00094144-01, NCGC00094144-04, NCGC00094144-05, NCGC00094144-06, NCGC00094144-07, NCGC00094144-11, NCGC00261496-01, AC-32982, alpha-Methyl-L-tyrosine, >=98% (TLC), AS-47139, SY099144, |A inverted exclamation mark-Methyl-L-Tyr, EU-0100811, NS00007101, L-TYROSINE, .ALPHA.-METHYL-, (-)-, C07921, D00762, EN300-127035, F12275, M 8131, F324725, Q6824116, BRD-K83766205-001-03-8, (S)-2-Amino-3-(4-hydroxyphenyl)-2-methylpropanoicacid, Z1255434943, (S)-a-Methyl-4-hydroxy phenylalanine, (S)-a-Methyltyrosine, Metyrosine, United States Pharmacopeia (USP) Reference Standard
Theoretical properties:
molecular_formula: C10H13NO3
molecular_weight: 195.21 g/mol
exact_mass: 195.08954328 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 3
heavy_atom_count: 14
topological_polar_surface_area: 83.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: Very slightly soluble
Descriptions:
pubchem: Alpha-methyl-L-tyrosine is an L-tyrosine derivative that consists of L-tyrosine bearing an additional methyl substituent at position 2. An inhibitor of the enzyme tyrosine 3-monooxygenase, and consequently of the synthesis of catecholamines. It is used to control the symptoms of excessive sympathetic stimulation in patients with pheochromocytoma. It has a role as an antihypertensive agent and an EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor. It is a L-tyrosine derivative and a non-proteinogenic L-alpha-amino acid.
chebi: An <small>L</small>-tyrosine derivative that consists of <small>L</small>-tyrosine bearing an additional methyl substituent at position 2. An inhibitor of the enzyme tyrosine 3-monooxygenase, and consequently of the synthesis of catecholamines. It is used to control the symptoms of excessive sympathetic stimulation in patients with pheochromocytoma.
chembl: METYROSINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: 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. AMPT inhibits tyrosine hydroxylase whose enzymatic activity is normally regulated through the phosphorylation of different serine residues in regulatory domain sites. 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.
It has been used in the treatment of pheochromocytoma.  It has been demonstrated to inhibit the production of melanin. It is available as a generic medication.