Metyrosine (CHEM016788)

Record Information
Version1.0
Creation Date2016-05-22 03:43:42 UTC
Update Date2026-08-18 00:34:37 UTC
Accession NumberCHEM016788
Identification
Common NameMetyrosine
ClassSmall Molecule
Description
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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(-)-alpha-Methyl-L-tyrosineChEBI
(S)-alpha-MethyltyrosineChEBI
alpha-Methyl-L-p-tyrosineChEBI
alpha-Methyl-p-tyrosineChEBI
alpha-Methyl-para-tyrosineChEBI
alpha-MethyltyrosineChEBI
L-alpha-MethyltyrosineChEBI
MethyltyrosineChEBI
MetirosinaChEBI
MetirosineChEBI
MetirosinumChEBI
DemserKegg
(-)-a-Methyl-L-tyrosineGenerator
(-)-Α-methyl-L-tyrosineGenerator
(S)-a-MethyltyrosineGenerator
(S)-Α-methyltyrosineGenerator
a-Methyl-L-p-tyrosineGenerator
Α-methyl-L-p-tyrosineGenerator
a-Methyl-p-tyrosineGenerator
Α-methyl-p-tyrosineGenerator
a-Methyl-para-tyrosineGenerator
Α-methyl-para-tyrosineGenerator
a-MethyltyrosineGenerator
Α-methyltyrosineGenerator
L-a-MethyltyrosineGenerator
L-Α-methyltyrosineGenerator
alpha Methyltyrosine hydrochlorideHMDB
alpha-Methyltyrosine, (+,-)-isomerHMDB
alpha MPTHMDB
alpha Methyl para tyrosineHMDB
alpha-MPTHMDB
alpha-Methyltyrosine, (D,L)-isomerHMDB
alpha-Methyltyrosine, (L)-isomerHMDB
Hydrochloride, alpha-methyltyrosineHMDB
Metyrosine merck brandHMDB
RacemetirosineHMDB
alpha Methyl p tyrosineHMDB
Merck brand OF metyrosineHMDB
Merck sharp and dohme brand OF metyrosineHMDB
alpha MethyltyrosineHMDB
alpha-Methyltyrosine hydrochlorideHMDB
alpha-Methyl- DL-tyrosineHMDB
a-Methyl-L-tyrosineHMDB
Α-methyl-L-tyrosineHMDB
MetyrosineChEBI
Chemical FormulaC10H13NO3
Average Molecular Mass195.215 g/mol
Monoisotopic Mass195.090 g/mol
CAS Registry Number672-87-7
IUPAC Name(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
Traditional Namemetyrosine
SMILESC[C@](N)(CC1=CC=C(O)C=C1)C(O)=O
InChI IdentifierInChI=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
InChI KeyNHTGHBARYWONDQ-JTQLQIEISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • D-alpha-amino acid
  • Phenylpropane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.48 g/LALOGPS
logP-1.9ALOGPS
logP-1.1ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.06ChemAxon
pKa (Strongest Basic)9.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.81 m³·mol⁻¹ChemAxon
Polarizability19.9 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00765
HMDB IDHMDB0014903
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMetirosine
Chemspider ID390103
ChEBI ID6912
PubChem Compound ID441350
Kegg Compound IDC07921
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=28716505
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=29353821
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=29438107
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=29668781