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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2018-05-20 20:12:09 UTC
HMDB IDHMDB0014903
Secondary Accession Numbers
  • HMDB14903
Metabolite Identification
Common NameMetyrosine
DescriptionMetyrosine is only found in individuals that have used or taken this drug. It is 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. (Martindale, The Extra Pharmacopoeia, 30th ed)Metyrosine inhibits tyrosine hydroxylase, which catalyzes the first transformation in catecholamine biosynthesis, i.e., the conversion of tyrosine to dihydroxyphenylalanine (DOPA). Because the first step is also the rate-limiting step, blockade of tyrosine hydroxylase activity results in decreased endogenous levels of catecholamines and their synthesis. This consequently, depletes the levels of the catecholamines dopamine, adrenaline and noradrenaline in the body,usually measured as decreased urinary excretion of catecholamines and their metabolites. One main end result of the catecholamine depletion is a decrease in blood presure.
Structure
Thumb
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
(-)-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
DemserMeSH
alpha Methyltyrosine hydrochlorideMeSH
alpha-Methyltyrosine, (+,-)-isomerMeSH
alpha MPTMeSH
alpha Methyl para tyrosineMeSH
alpha-MPTMeSH
alpha-Methyltyrosine, (D,L)-isomerMeSH
alpha-Methyltyrosine, (L)-isomerMeSH
Hydrochloride, alpha-methyltyrosineMeSH
Metyrosine merck brandMeSH
RacemetirosineMeSH
alpha Methyl P tyrosineMeSH
Merck brand OF metyrosineMeSH
Merck sharp and dohme brand OF metyrosineMeSH
alpha MethyltyrosineMeSH
alpha-Methyltyrosine hydrochlorideMeSH
alpha-Methyl- DL-tyrosineMeSH
Chemical FormulaC10H13NO3
Average Molecular Weight195.2151
Monoisotopic Molecular Weight195.089543287
IUPAC Name(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
Traditional Namemetyrosine
CAS Registry Number672-87-7
SMILES
C[C@](N)(CC1=CC=C(O)C=C1)C(O)=O
InChI Identifier
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
InChI KeyNHTGHBARYWONDQ-JTQLQIEISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These 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
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point312.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.48 g/LNot Available
LogP-1.7Not 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-4900000000-946ec0a9cb27d9dde874View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fu-9651000000-11b1bed7129ec3e5c27aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-7b2e7907b466193628f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-8ee69272ff1683e7b679View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-3900000000-95f4506f225bff0a13e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3900000000-9aec0e31d6c52c6d4218View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9500000000-ea5a5dcd5c96018a361eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kac-7900000000-25650809bb77fee5eb83View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00765 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00765 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00765
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID390103
KEGG Compound IDC07921
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetirosine
METLIN IDNot Available
PubChem Compound441350
PDB IDNot Available
ChEBI ID6912
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Plays an important role in the physiology of adrenergic neurons.
Gene Name:
TH
Uniprot ID:
P07101
Molecular weight:
55611.26
References
  1. Nasrallah HA, Donnelly EF, Bigelow LB, Rivera-Calimlim L, Rogol A, Potkin S, Rauscher FP, Wyatt RJ: Inhibition of dopamine synthesis in chronic schizophrenia. Clinical ineffectiveness of metyrosine. Arch Gen Psychiatry. 1977 Jun;34(6):649-55. [PubMed:17374 ]
  2. Yoshimoto Y, Nakaso K, Nakashima K: L-dopa and dopamine enhance the formation of aggregates under proteasome inhibition in PC12 cells. FEBS Lett. 2005 Feb 14;579(5):1197-202. Epub 2005 Jan 21. [PubMed:15710413 ]
  3. Shore PA, Dorris RL: On a prime role for newly synthesized dopamine in striatal function. Eur J Pharmacol. 1975 Feb;30(2):315-8. [PubMed:1168577 ]
  4. Moore KE, Demarest KT, Johnston CA: Influence of prolactin on dopaminergic neuronal systems in the hypothalamus. Fed Proc. 1980 Sep;39(11):2912-6. [PubMed:7409209 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]