Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2006-08-13 02:17:17 UTC |
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Update Date | 2023-02-21 17:16:45 UTC |
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HMDB ID | HMDB0003633 |
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Secondary Accession Numbers | - HMDB0060283
- HMDB0060284
- HMDB03633
- HMDB60283
- HMDB60284
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Metabolite Identification |
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Common Name | N-Methyltyramine |
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Description | N-methyltyramine (NMT) is a phenolic amine. NMT is a potent stimulant of gastrin release present in alcoholic beverages produced by alcoholic fermentation, but not by distillation (i.e.: beer.). NMT is well absorbed in the small intestine, especially in the duodenum and jejunum. NMT is metabolized in the liver (the site of first-pass metabolism), but not in the small-intestinal mucosa. NMT is occasionally present in the stools of children and infants. Satisfactory results have been obtained in treating infective shock with injection of natural Fructus Aurantii immaturus (nat-FAI); the anti-shock effective compositions in FAI have been proved to be synephrine and NMT. (PMID: 10772638 , 2570680 ). |
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Structure | InChI=1S/C9H13NO/c1-10-7-6-8-2-4-9(11)5-3-8/h2-5,10-11H,6-7H2,1H3 |
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Synonyms | Value | Source |
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4-Hydroxy-N-methylphenethylamine | ChEBI | Methyl-4-tyramine | ChEBI | p-(2-Methylaminoethyl)phenol | ChEBI | 4-(2-(Methylamino)ethyl)-phenol | HMDB | 4-(2-Methylaminoethyl)phenol | HMDB | 4-[2-(Methylamino)ethyl]-phenol | HMDB | 4-[2-(Methylamino)ethyl]phenol | HMDB | Methyl tyramine | HMDB | N-Methyl-p-tyramine | HMDB | N-Methyltyraminium | HMDB | NMT | HMDB | p-(2-(Methylamino)ethyl)phenol | HMDB | p-[2-(Methylamino)ethyl]-phenol | HMDB | {p-[2-(methylamino)ethyl]phenol} | HMDB | N-Methyltyrosamine | HMDB | Methyl-4-tyramine hydrochloride | HMDB | Methyl-4-tyramine hydrobromide | HMDB |
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Chemical Formula | C9H13NO |
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Average Molecular Weight | 151.2056 |
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Monoisotopic Molecular Weight | 151.099714043 |
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IUPAC Name | 4-[2-(methylamino)ethyl]phenol |
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Traditional Name | N-methyltyramine |
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CAS Registry Number | 370-98-9 |
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SMILES | CNCCC1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C9H13NO/c1-10-7-6-8-2-4-9(11)5-3-8/h2-5,10-11H,6-7H2,1H3 |
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InChI Key | AXVZFRBSCNEKPQ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Phenethylamines |
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Direct Parent | Phenethylamines |
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Alternative Parents | |
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Substituents | - Phenethylamine
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Phenol
- Secondary amine
- Secondary aliphatic amine
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- 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 | |
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Process | Not Available |
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Role | |
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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 | 1.455 | 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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N-Methyltyramine,1TMS,isomer #1 | CNCCC1=CC=C(O[Si](C)(C)C)C=C1 | 1473.5 | Semi standard non polar | 33892256 | N-Methyltyramine,1TMS,isomer #2 | CN(CCC1=CC=C(O)C=C1)[Si](C)(C)C | 1666.6 | Semi standard non polar | 33892256 | N-Methyltyramine,2TMS,isomer #1 | CN(CCC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C | 1702.1 | Semi standard non polar | 33892256 | N-Methyltyramine,2TMS,isomer #1 | CN(CCC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C | 1693.0 | Standard non polar | 33892256 | N-Methyltyramine,2TMS,isomer #1 | CN(CCC1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C | 1749.5 | Standard polar | 33892256 | N-Methyltyramine,1TBDMS,isomer #1 | CNCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 | 1714.0 | Semi standard non polar | 33892256 | N-Methyltyramine,1TBDMS,isomer #2 | CN(CCC1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C | 1881.3 | Semi standard non polar | 33892256 | N-Methyltyramine,2TBDMS,isomer #1 | CN(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C | 2183.1 | Semi standard non polar | 33892256 | N-Methyltyramine,2TBDMS,isomer #1 | CN(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C | 2172.1 | Standard non polar | 33892256 | N-Methyltyramine,2TBDMS,isomer #1 | CN(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C | 2040.8 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - N-Methyltyramine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9200000000-14293e75666be4e27019 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Methyltyramine GC-MS (1 TMS) - 70eV, Positive | splash10-00xr-7920000000-4709651ba3c22c23b463 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Methyltyramine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0006-9000000000-89ff5a43bc3e7737bcb6 | 2015-03-01 | Not Available | 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 - N-Methyltyramine 10V, Positive-QTOF | splash10-0uk9-0900000000-0f335d13104342fdeed5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Methyltyramine 20V, Positive-QTOF | splash10-0fk9-2900000000-037595c7cc0c504058c6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Methyltyramine 40V, Positive-QTOF | splash10-0kk9-9500000000-376efc98f806aac30929 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Methyltyramine 10V, Negative-QTOF | splash10-0udi-0900000000-27ea78b166d8b3172ce1 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Methyltyramine 20V, Negative-QTOF | splash10-0udi-1900000000-fb693eca1267a0ba9685 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Methyltyramine 40V, Negative-QTOF | splash10-05al-6900000000-6d964137e90c9e3293d1 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Methyltyramine 10V, Positive-QTOF | splash10-00di-1900000000-6ac9e0419aa31060260b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Methyltyramine 20V, Positive-QTOF | splash10-00dl-7900000000-7fd4cbc25b6ff2a2bf1e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Methyltyramine 40V, Positive-QTOF | splash10-004l-9100000000-7021336d37b527e2e5fd | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Methyltyramine 10V, Negative-QTOF | splash10-0udi-0900000000-1c71ef4ed8c1b09fb863 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Methyltyramine 20V, Negative-QTOF | splash10-0udi-0900000000-4f21e6ca90b01b880bf4 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Methyltyramine 40V, Negative-QTOF | splash10-00kf-9600000000-4a0119f5c8223bec2ae4 | 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 (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+) | 2022-02-11 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-) | 2022-02-11 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB000435 |
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KNApSAcK ID | C00027432 |
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Chemspider ID | 9345 |
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KEGG Compound ID | C02442 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | N-Methyltyramine |
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METLIN ID | Not Available |
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PubChem Compound | 9727 |
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PDB ID | Not Available |
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ChEBI ID | 17458 |
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Food Biomarker Ontology | Not Available |
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VMH ID | C02442 |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
- Kimura T, Iwasaki N, Yokoe JI, Haruta S, Yokoo Y, Ogawara KI, Higaki K: Analysis and prediction of absorption profile including hepatic first-pass metabolism of N-methyltyramine, a potent stimulant of gastrin release present in beer, after oral ingestion in rats by gastrointestinal-transit-absorption model. Drug Metab Dispos. 2000 May;28(5):577-81. [PubMed:10772638 ]
- Zhao XW, Li JX, Zhu ZR, Sun DQ, Liu SC: Anti-shock effects of synthetic effective compositions of fructus aurantii immaturus. Experimental study and clinical observation. Chin Med J (Engl). 1989 Feb;102(2):91-3. [PubMed:2570680 ]
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