Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-01-09 12:11:23 UTC
Update Date2023-02-21 17:29:15 UTC
HMDB IDHMDB0059720
Secondary Accession Numbers
  • HMDB59720
Metabolite Identification
Common NameMeta-Tyrosine
DescriptionMeta-Tyrosine, also known as L-m-tyr or m-tyrosine, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. A hydroxyphenylalanine that is L-phenylalanine with a substituent hydroxy group at position 3. Meta-Tyrosine is a very strong basic compound (based on its pKa).
Structure
Data?1677000555
Synonyms
ValueSource
L-m-TyrChEBI
L-MTyrChEBI
m-TyrosineChEBI
(2S)-2-Azaniumyl-3-(3-hydroxyphenyl)propanoateHMDB
Meta-tyrosineChEBI
Chemical FormulaC9H11NO3
Average Molecular Weight181.1885
Monoisotopic Molecular Weight181.073893223
IUPAC Name(2S)-2-amino-3-(3-hydroxyphenyl)propanoic acid
Traditional Namemeta-tyrosine
CAS Registry NumberNot Available
SMILES
N[C@@H](CC1=CC=CC(O)=C1)C(O)=O
InChI Identifier
InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-2-1-3-7(11)4-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1
InChI KeyJZKXXXDKRQWDET-QMMMGPOBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • L-alpha-amino acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.13 g/LALOGPS
logP-2.3ALOGPS
logP-1.5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.1 m³·mol⁻¹ChemAxon
Polarizability18.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.45631661259
DarkChem[M-H]-139.65731661259
DeepCCS[M+H]+137.9830932474
DeepCCS[M-H]-135.58530932474
DeepCCS[M-2H]-170.89930932474
DeepCCS[M+Na]+145.65230932474
AllCCS[M+H]+140.432859911
AllCCS[M+H-H2O]+136.232859911
AllCCS[M+NH4]+144.332859911
AllCCS[M+Na]+145.532859911
AllCCS[M-H]-137.832859911
AllCCS[M+Na-2H]-138.632859911
AllCCS[M+HCOO]-139.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Meta-TyrosineN[C@@H](CC1=CC=CC(O)=C1)C(O)=O3147.8Standard polar33892256
Meta-TyrosineN[C@@H](CC1=CC=CC(O)=C1)C(O)=O1871.8Standard non polar33892256
Meta-TyrosineN[C@@H](CC1=CC=CC(O)=C1)C(O)=O2097.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Meta-Tyrosine,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC(C[C@H](N)C(=O)O)=C11881.7Semi standard non polar33892256
Meta-Tyrosine,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=CC(O)=C11900.3Semi standard non polar33892256
Meta-Tyrosine,1TMS,isomer #3C[Si](C)(C)N[C@@H](CC1=CC=CC(O)=C1)C(=O)O1960.8Semi standard non polar33892256
Meta-Tyrosine,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=CC(O[Si](C)(C)C)=C11852.0Semi standard non polar33892256
Meta-Tyrosine,2TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CC=CC(O[Si](C)(C)C)=C1)C(=O)O1935.6Semi standard non polar33892256
Meta-Tyrosine,2TMS,isomer #3C[Si](C)(C)N[C@@H](CC1=CC=CC(O)=C1)C(=O)O[Si](C)(C)C1933.5Semi standard non polar33892256
Meta-Tyrosine,2TMS,isomer #4C[Si](C)(C)N([C@@H](CC1=CC=CC(O)=C1)C(=O)O)[Si](C)(C)C2129.8Semi standard non polar33892256
Meta-Tyrosine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=CC(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C1886.5Semi standard non polar33892256
Meta-Tyrosine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=CC(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C1943.2Standard non polar33892256
Meta-Tyrosine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=CC(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C2083.5Standard polar33892256
Meta-Tyrosine,3TMS,isomer #2C[Si](C)(C)OC1=CC=CC(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C12086.6Semi standard non polar33892256
Meta-Tyrosine,3TMS,isomer #2C[Si](C)(C)OC1=CC=CC(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C11996.2Standard non polar33892256
Meta-Tyrosine,3TMS,isomer #2C[Si](C)(C)OC1=CC=CC(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C12213.7Standard polar33892256
Meta-Tyrosine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O)=C1)N([Si](C)(C)C)[Si](C)(C)C2086.5Semi standard non polar33892256
Meta-Tyrosine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O)=C1)N([Si](C)(C)C)[Si](C)(C)C2071.2Standard non polar33892256
Meta-Tyrosine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O)=C1)N([Si](C)(C)C)[Si](C)(C)C2190.8Standard polar33892256
Meta-Tyrosine,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2107.6Semi standard non polar33892256
Meta-Tyrosine,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2056.0Standard non polar33892256
Meta-Tyrosine,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2036.6Standard polar33892256
Meta-Tyrosine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@H](N)C(=O)O)=C12123.4Semi standard non polar33892256
Meta-Tyrosine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=CC(O)=C12138.6Semi standard non polar33892256
Meta-Tyrosine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC(O)=C1)C(=O)O2189.6Semi standard non polar33892256
Meta-Tyrosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12321.2Semi standard non polar33892256
Meta-Tyrosine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O2424.6Semi standard non polar33892256
Meta-Tyrosine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C2366.3Semi standard non polar33892256
Meta-Tyrosine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=CC(O)=C1)C(=O)O)[Si](C)(C)C(C)(C)C2525.4Semi standard non polar33892256
Meta-Tyrosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C2581.1Semi standard non polar33892256
Meta-Tyrosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C2558.7Standard non polar33892256
Meta-Tyrosine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C2460.9Standard polar33892256
Meta-Tyrosine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12792.2Semi standard non polar33892256
Meta-Tyrosine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12608.1Standard non polar33892256
Meta-Tyrosine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12517.6Standard polar33892256
Meta-Tyrosine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2743.4Semi standard non polar33892256
Meta-Tyrosine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2673.0Standard non polar33892256
Meta-Tyrosine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2492.2Standard polar33892256
Meta-Tyrosine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2985.9Semi standard non polar33892256
Meta-Tyrosine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2812.1Standard non polar33892256
Meta-Tyrosine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2471.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Meta-Tyrosine GC-MS (2 TMS)splash10-0a4j-3940000000-1f2530cb7cb335d32e402014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Meta-Tyrosine GC-MS (3 TMS)splash10-014i-1890000000-b3a4950b74f78e8b1f1d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Meta-Tyrosine GC-MS (Non-derivatized)splash10-0a4j-3940000000-1f2530cb7cb335d32e402017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Meta-Tyrosine GC-MS (Non-derivatized)splash10-014i-1890000000-b3a4950b74f78e8b1f1d2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Meta-Tyrosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-4900000000-591bb41c5e030f74ea662017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Meta-Tyrosine GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-5490000000-42f7ab53cd22e78f04452017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Meta-Tyrosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Meta-Tyrosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meta-Tyrosine 10V, Positive-QTOFsplash10-0019-0900000000-b8767a6e66ce78d074fe2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meta-Tyrosine 20V, Positive-QTOFsplash10-000i-0900000000-1823a449a868e6cb15d92017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meta-Tyrosine 40V, Positive-QTOFsplash10-0aou-8900000000-41bb52abc360a513786f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meta-Tyrosine 10V, Negative-QTOFsplash10-001i-0900000000-b18debca081bd463b44a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meta-Tyrosine 20V, Negative-QTOFsplash10-001i-0900000000-8746c93314cbf487b1622017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meta-Tyrosine 40V, Negative-QTOFsplash10-00di-7900000000-ff5570ce952504e521902017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meta-Tyrosine 10V, Negative-QTOFsplash10-001i-0900000000-d53e2fc548e85a34e3542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meta-Tyrosine 20V, Negative-QTOFsplash10-0a59-2900000000-40620082cf7f28183d992021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meta-Tyrosine 40V, Negative-QTOFsplash10-00di-9300000000-846198ac6486a67bd92e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meta-Tyrosine 10V, Positive-QTOFsplash10-000i-0900000000-95c143a50c7ec998d74f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meta-Tyrosine 20V, Positive-QTOFsplash10-014r-1900000000-287fa4087ac7b5d3057b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Meta-Tyrosine 40V, Positive-QTOFsplash10-014l-9800000000-d273f5699848ac90e15d2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03552
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5323512
KEGG Compound IDNot Available
BioCyc IDCPD-14541
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6950577
PDB IDMTY
ChEBI ID44303
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gloge A, Langer B, Poppe L, Retey J: The behavior of substrate analogues and secondary deuterium isotope effects in the phenylalanine ammonia-lyase reaction. Arch Biochem Biophys. 1998 Nov 1;359(1):1-7. [PubMed:9799553 ]
  2. Engel J: Metatyrosine-induced reversal of the suppression of the conditioned avoidance response in reserpine-treated rats. Acta Pharmacol Toxicol (Copenh). 1971;30(3):278-88. [PubMed:4945487 ]
  3. CARLSSON A, LINDQVIST M: In-vivo decarboxylation of alpha-methyl DOPA and alpha-methyl metatyrosine. Acta Physiol Scand. 1962 Jan;54:87-94. [PubMed:13876658 ]
  4. Jagoda EM, Vaquero JJ, Seidel J, Green MV, Eckelman WC: Experiment assessment of mass effects in the rat: implications for small animal PET imaging. Nucl Med Biol. 2004 Aug;31(6):771-9. [PubMed:15246368 ]
  5. HESS SM, CONNAMACHER RH, OZAKI M, UDENFRIEND S: The effects of alpha-methyl-DOPA and alpha-methyl-metatyrosine on the metabolism of norepinephrine and serotonin in vivo. J Pharmacol Exp Ther. 1961 Nov;134:129-38. [PubMed:13907002 ]
  6. Shellenberger MK, Elder JT: Alterations in rabbit core temperature produced by alpha-methyl metatyrosine. Eur J Pharmacol. 1968 Jun;3(3):196-202. [PubMed:5673633 ]
  7. Hermand E, Leonardelli J, Tramu G: [Hypothalamic mechanism of the antiovulatory action of sulpiride]. Encephale. 1975;1(4):375-82. [PubMed:767098 ]
  8. ANDEN NE: ON THE MECHANISM OF NORADRENALINE DEPLETION BY ALPHA-METHYL METATYROSINE AND METARAMINOL. Acta Pharmacol Toxicol (Copenh). 1964;21:260-71. [PubMed:14209617 ]
  9. Magsino CH Jr, Hamouda W, Bapna V, Ghanim H, Abu-Reish IA, Aljada A, Dandona P: Nadolol inhibits reactive oxygen species generation by leukocytes and linoleic acid oxidation. Am J Cardiol. 2000 Aug 15;86(4):443-8. [PubMed:10946040 ]
  10. Kimura K, Kimura Y, Ohata K, Takagi H: Effects of several monoamine-related compounds on the reserpine-induced spikes recorded from the medial nucleus trapezoides in rabbits. Jpn J Pharmacol. 1978 Apr;28(2):317-27. [PubMed:211305 ]
  11. Carlsson A, Lindqvist M: Metatyrosine as a tool for selective protection of catecholamine stores against reserpine. Eur J Pharmacol. 1967 Dec;2(3):187-92. [PubMed:5590341 ]
  12. Blaschiko H, Longlands MG: Some observations on the bacterial decarboxylation of metatyrosine. Naunyn Schmiedebergs Arch Pharmacol. 1972;273(4):430-3. [PubMed:4262104 ]
  13. Anden NE, Fuxe K, Henning M: Mechanisms of noradrenaline and 5-hydroxytryptamine disappearance induced by alpha-methyl-dopa and alpha-methyl-metatyrosine. Eur J Pharmacol. 1969 Dec;8(3):302-9. [PubMed:5263681 ]
  14. Singh PP, Das PK: Role of catecholamines in the hypothermic activity of cannabis in albino rats. Psychopharmacology (Berl). 1976 Nov 10;50(2):199-204. [PubMed:826962 ]
  15. HAGEN P: Observations on the substrate specificity of DOPA decarboxylase from ox adrenal medulla, human phaeochromocytoma and human argentaffinoma. Br J Pharmacol Chemother. 1962 Feb;18:175-82. [PubMed:13903593 ]
  16. Sandler M, Corne SJ, Stephens R, Shaw DM, Hunter DR, Stern GM: Metatyrosine in the treatment of parkinsonism. Lancet. 1972 Sep 16;2(7777):605. [PubMed:4115783 ]