Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-01-09 12:11:23 UTC |
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Update Date | 2023-02-21 17:29:15 UTC |
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HMDB ID | HMDB0059720 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Meta-Tyrosine |
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Description | Meta-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). |
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Structure | N[C@@H](CC1=CC=CC(O)=C1)C(O)=O 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 |
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Synonyms | Value | Source |
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L-m-Tyr | ChEBI | L-MTyr | ChEBI | m-Tyrosine | ChEBI | (2S)-2-Azaniumyl-3-(3-hydroxyphenyl)propanoate | HMDB | Meta-tyrosine | ChEBI |
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Chemical Formula | C9H11NO3 |
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Average Molecular Weight | 181.1885 |
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Monoisotopic Molecular Weight | 181.073893223 |
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IUPAC Name | (2S)-2-amino-3-(3-hydroxyphenyl)propanoic acid |
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Traditional Name | meta-tyrosine |
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CAS Registry Number | Not Available |
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SMILES | N[C@@H](CC1=CC=CC(O)=C1)C(O)=O |
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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 |
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InChI Key | JZKXXXDKRQWDET-QMMMGPOBSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Phenylalanine and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Meta-Tyrosine,1TMS,isomer #1 | C[Si](C)(C)OC1=CC=CC(C[C@H](N)C(=O)O)=C1 | 1881.7 | Semi standard non polar | 33892256 | Meta-Tyrosine,1TMS,isomer #2 | C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=CC(O)=C1 | 1900.3 | Semi standard non polar | 33892256 | Meta-Tyrosine,1TMS,isomer #3 | C[Si](C)(C)N[C@@H](CC1=CC=CC(O)=C1)C(=O)O | 1960.8 | Semi standard non polar | 33892256 | Meta-Tyrosine,2TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=CC(O[Si](C)(C)C)=C1 | 1852.0 | Semi standard non polar | 33892256 | Meta-Tyrosine,2TMS,isomer #2 | C[Si](C)(C)N[C@@H](CC1=CC=CC(O[Si](C)(C)C)=C1)C(=O)O | 1935.6 | Semi standard non polar | 33892256 | Meta-Tyrosine,2TMS,isomer #3 | C[Si](C)(C)N[C@@H](CC1=CC=CC(O)=C1)C(=O)O[Si](C)(C)C | 1933.5 | Semi standard non polar | 33892256 | Meta-Tyrosine,2TMS,isomer #4 | C[Si](C)(C)N([C@@H](CC1=CC=CC(O)=C1)C(=O)O)[Si](C)(C)C | 2129.8 | Semi standard non polar | 33892256 | Meta-Tyrosine,3TMS,isomer #1 | C[Si](C)(C)N[C@@H](CC1=CC=CC(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C | 1886.5 | Semi standard non polar | 33892256 | Meta-Tyrosine,3TMS,isomer #1 | C[Si](C)(C)N[C@@H](CC1=CC=CC(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C | 1943.2 | Standard non polar | 33892256 | Meta-Tyrosine,3TMS,isomer #1 | C[Si](C)(C)N[C@@H](CC1=CC=CC(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C | 2083.5 | Standard polar | 33892256 | Meta-Tyrosine,3TMS,isomer #2 | C[Si](C)(C)OC1=CC=CC(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C1 | 2086.6 | Semi standard non polar | 33892256 | Meta-Tyrosine,3TMS,isomer #2 | C[Si](C)(C)OC1=CC=CC(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C1 | 1996.2 | Standard non polar | 33892256 | Meta-Tyrosine,3TMS,isomer #2 | C[Si](C)(C)OC1=CC=CC(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=C1 | 2213.7 | Standard polar | 33892256 | Meta-Tyrosine,3TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O)=C1)N([Si](C)(C)C)[Si](C)(C)C | 2086.5 | Semi standard non polar | 33892256 | Meta-Tyrosine,3TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O)=C1)N([Si](C)(C)C)[Si](C)(C)C | 2071.2 | Standard non polar | 33892256 | Meta-Tyrosine,3TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O)=C1)N([Si](C)(C)C)[Si](C)(C)C | 2190.8 | Standard polar | 33892256 | Meta-Tyrosine,4TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C | 2107.6 | Semi standard non polar | 33892256 | Meta-Tyrosine,4TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C | 2056.0 | Standard non polar | 33892256 | Meta-Tyrosine,4TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](CC1=CC=CC(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C | 2036.6 | Standard polar | 33892256 | Meta-Tyrosine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=CC(C[C@H](N)C(=O)O)=C1 | 2123.4 | Semi standard non polar | 33892256 | Meta-Tyrosine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=CC(O)=C1 | 2138.6 | Semi standard non polar | 33892256 | Meta-Tyrosine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC(O)=C1)C(=O)O | 2189.6 | Semi standard non polar | 33892256 | Meta-Tyrosine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1 | 2321.2 | Semi standard non polar | 33892256 | Meta-Tyrosine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O | 2424.6 | Semi standard non polar | 33892256 | Meta-Tyrosine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C | 2366.3 | Semi standard non polar | 33892256 | Meta-Tyrosine,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=CC(O)=C1)C(=O)O)[Si](C)(C)C(C)(C)C | 2525.4 | Semi standard non polar | 33892256 | Meta-Tyrosine,3TBDMS,isomer #1 | CC(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)C | 2581.1 | Semi standard non polar | 33892256 | Meta-Tyrosine,3TBDMS,isomer #1 | CC(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)C | 2558.7 | Standard non polar | 33892256 | Meta-Tyrosine,3TBDMS,isomer #1 | CC(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)C | 2460.9 | Standard polar | 33892256 | Meta-Tyrosine,3TBDMS,isomer #2 | CC(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)=C1 | 2792.2 | Semi standard non polar | 33892256 | Meta-Tyrosine,3TBDMS,isomer #2 | CC(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)=C1 | 2608.1 | Standard non polar | 33892256 | Meta-Tyrosine,3TBDMS,isomer #2 | CC(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)=C1 | 2517.6 | Standard polar | 33892256 | Meta-Tyrosine,3TBDMS,isomer #3 | CC(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)C | 2743.4 | Semi standard non polar | 33892256 | Meta-Tyrosine,3TBDMS,isomer #3 | CC(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)C | 2673.0 | Standard non polar | 33892256 | Meta-Tyrosine,3TBDMS,isomer #3 | CC(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)C | 2492.2 | Standard polar | 33892256 | Meta-Tyrosine,4TBDMS,isomer #1 | CC(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)C | 2985.9 | Semi standard non polar | 33892256 | Meta-Tyrosine,4TBDMS,isomer #1 | CC(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)C | 2812.1 | Standard non polar | 33892256 | Meta-Tyrosine,4TBDMS,isomer #1 | CC(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)C | 2471.6 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Meta-Tyrosine GC-MS (2 TMS) | splash10-0a4j-3940000000-1f2530cb7cb335d32e40 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Meta-Tyrosine GC-MS (3 TMS) | splash10-014i-1890000000-b3a4950b74f78e8b1f1d | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Meta-Tyrosine GC-MS (Non-derivatized) | splash10-0a4j-3940000000-1f2530cb7cb335d32e40 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Meta-Tyrosine GC-MS (Non-derivatized) | splash10-014i-1890000000-b3a4950b74f78e8b1f1d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Meta-Tyrosine GC-MS (Non-derivatized) - 70eV, Positive | splash10-000i-4900000000-591bb41c5e030f74ea66 | 2017-08-28 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Meta-Tyrosine GC-MS (2 TMS) - 70eV, Positive | splash10-0a4i-5490000000-42f7ab53cd22e78f0445 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Meta-Tyrosine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Meta-Tyrosine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meta-Tyrosine 10V, Positive-QTOF | splash10-0019-0900000000-b8767a6e66ce78d074fe | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meta-Tyrosine 20V, Positive-QTOF | splash10-000i-0900000000-1823a449a868e6cb15d9 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meta-Tyrosine 40V, Positive-QTOF | splash10-0aou-8900000000-41bb52abc360a513786f | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meta-Tyrosine 10V, Negative-QTOF | splash10-001i-0900000000-b18debca081bd463b44a | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meta-Tyrosine 20V, Negative-QTOF | splash10-001i-0900000000-8746c93314cbf487b162 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meta-Tyrosine 40V, Negative-QTOF | splash10-00di-7900000000-ff5570ce952504e52190 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meta-Tyrosine 10V, Negative-QTOF | splash10-001i-0900000000-d53e2fc548e85a34e354 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meta-Tyrosine 20V, Negative-QTOF | splash10-0a59-2900000000-40620082cf7f28183d99 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meta-Tyrosine 40V, Negative-QTOF | splash10-00di-9300000000-846198ac6486a67bd92e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meta-Tyrosine 10V, Positive-QTOF | splash10-000i-0900000000-95c143a50c7ec998d74f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meta-Tyrosine 20V, Positive-QTOF | splash10-014r-1900000000-287fa4087ac7b5d3057b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Meta-Tyrosine 40V, Positive-QTOF | splash10-014l-9800000000-d273f5699848ac90e15d | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Hermand E, Leonardelli J, Tramu G: [Hypothalamic mechanism of the antiovulatory action of sulpiride]. Encephale. 1975;1(4):375-82. [PubMed:767098 ]
- ANDEN NE: ON THE MECHANISM OF NORADRENALINE DEPLETION BY ALPHA-METHYL METATYROSINE AND METARAMINOL. Acta Pharmacol Toxicol (Copenh). 1964;21:260-71. [PubMed:14209617 ]
- 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 ]
- 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 ]
- 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 ]
- Blaschiko H, Longlands MG: Some observations on the bacterial decarboxylation of metatyrosine. Naunyn Schmiedebergs Arch Pharmacol. 1972;273(4):430-3. [PubMed:4262104 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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