Compound: 658-48-0
SMILES: O=C(O)C(N)(Cc1ccc(O)cc1)C
InChIKey: NHTGHBARYWONDQ-UHFFFAOYSA-N
Synonyms: 658-48-0, alpha-Methyl-p-tyrosine, Racemetyrosine, Dl-metyrosine, alpha-Methyltyrosine, alpha-Methyl-dl-tyrosine, Tyrosine, alpha-methyl-, (+-)-alpha-Methyl-DL-tyrosine, alpha-Methylparatyrosine, DL-, DNP-01, X88TTO174Z, alpha-MPT, DTXSID90859529, SM-88 COMPONENT RACEMETYROSINE, DL-Tyrosine, alpha-methyl-, alpha MPT, alpha methyltyrosine, D,L-alpha-metyrosine, alpha Methyl p tyrosine, RefChem:900822, alpha Methyl para tyrosine, alpha-Methyltyrosine, (D,L)-, alpha-Methyltyrosine, (+,-)-, alpha Methyltyrosine Hydrochloride, DTXCID20209290, SM 88, Hydrochloride, alpha-Methyltyrosine, alpha-Methyl-para-tyrosine, Racemetirosine, 2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid, DL-alpha-Methyltyrosine, DL-alpha-Methyl-p-tyrosine, 620-30-4, Racemetirosina, Racemetirosine [INN], AMPT, 2-P-HYDROXYPHENYLMETHYL-DL-ALANINE, MFCD00004187, .alpha.-Methyltyrosine, Dl-2-methyl-p-tyrosine, D,l-metyrosine, Tyrosine, .alpha.-methyl-, DL-2-Methyl-3-(4-hydroxyphenyl)alanine, Racemetyrosine [USAN], .alpha.-Methyl-p-tyrosine, SM-88, Racemetirosinum, Racemetyrosine (USAN), 2-(4-hydroxybenzyl)-2-aminopropanoic acid, L1-79, Racemetirosinum [INN-Latin], Racemetirosina [INN-Spanish], A-METHYL-DL-P-TYROSINE, Metyrosine, DL-, L-2-Methyl-3-(4-hydroxy-phenyl)alanine, a-Methyl-D,L-tyrosine (L-isomer enriched), EINECS 210-635-7, EINECS 211-523-0, H 9/88, BRN 2938704, UNII-X88TTO174Z, (R,S)-2-Amino-3-(4-hydroxyphenyl)-2-methylpropionsaeure, AI3-62542, Metyrosine impurity, 4-Hydroxy-alpha-methylphenylalanine, -Methyl-p-tyrosine, DL-a-methyltyrosine, a-Methyl-DL-tyrosine, ?-Methyl-D,L-tyrosine, D,L-alpha-methyltyrosine, dl-.alpha.-Methyltyrosine, Racemetirosine [WHO-DD], Racemetyrosine (SM-88), .alpha.-Methylparatyrosine, M-5185, .alpha.-Methyl-dl-tyrosine, alpha -Methyl-D,L-tyrosine, Lopac0_000001, SCHEMBL61871, 4-14-00-02453 (Beilstein Handbook Reference), MLS000028638, dl-.alpha.-Methyl-p-tyrosine, 2-Amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid, 2-amino-3-(4-hydroxyphenyl)-2-methyl-propanoic acid, GTPL5094, orb1306564, CHEMBL1330596, alpha-Methyl-DL-tyrosine, 98%, |A-Methyl-D pound notL-tyrosine, CHEBI:232408, HMS3260A03, CS-D0593, WHO 4292, Tox21_500001, EBC-06361, s9713, SBB015064, STK272180, AKOS003391424, AKOS022063174, CCG-204097, DS-6468, LP00001, SDCCGSBI-0049990.P002, (.+/-.)-.alpha.-Methyl-DL-tyrosine, NCGC00015701-03, NCGC00015701-04, NCGC00015701-05, NCGC00015701-07, NCGC00093528-01, NCGC00093528-02, NCGC00260686-01, alpha-Methyl-DL-tyrosine, >=95% (NT), HY-33549, RACEMETYROSINE COMPONENT OF SM-88, SMR000059140, ST075173, SY045851, DB-054045, DB-055009, EU-0100001, NS00080214, D11606, EN300-314129, F303151, SR-01000075605, SR-01000075607, 2-amino-3-(4-hydroxyphenyl)-2-methylpropanoicacid, 2-Amino-3-(4-hydroxyphenyl)-2-methylpropionic acid, SR-01000075605-1, SR-01000075607-1, Q15408417
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:
Descriptions:
pubchem: Racemetirosine is an EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor.
chembl: RACEMETYROSINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
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.