Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:34 UTC |
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Update date | 2020-09-17 15:42:26 UTC |
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Primary ID | FDB000433 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Tyramine |
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Description | Tyramine is a monoamine compound derived from the amino acid tyrosine. It is a very strong basic compound (based on its pKa). Tyramine is metabolized by the enzyme monoamine oxidase. In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. Foods containing considerable amounts of tyramine include fish (herring), chocolate, alcoholic beverages, cheese, yogurt, soy sauce, sauerkraut, and processed meat. Tyramine in the blood or urine is often considered as a biomarker for the consumption of cheese. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more and induce migraine headaches (PMID: 27424325). The tyramine connection to hypertensive episodes was discovered by a British pharmacist whose wife was taking an monoamine oxidase inhibitors (MAOI). He noticed that every time they had a meal with cheese, she would get a severe headache (PMID: 19742203). Tyramine acts as a neurotransmitter via a G protein-coupled receptor called TA1, which has a high affinity for tyramine. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. As an indirect sympathomimetic compound, tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase, so it prolongs the actions of adrenergic transmitters. Tyramine also provokes transmitter release from adrenergic terminals. |
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CAS Number | 51-67-2 |
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Structure | |
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Synonyms | Synonym | Source |
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2-(p-Hydroxyphenyl)ethylamine | ChEBI | 4-Hydroxy-beta-phenylethylamine | ChEBI | 4-Hydroxyphenethylamine | ChEBI | 4-Hydroxyphenylethylamine | ChEBI | beta-(4-Hydroxyphenyl)ethylamine | ChEBI | p-(2-Aminoethyl)phenol | ChEBI | p-Hydroxyphenethylamine | ChEBI | p-Hydroxyphenylethylamine | ChEBI | p-Tyramine | ChEBI | Tyramin | ChEBI | 4-Hydroxy-b-phenylethylamine | Generator | 4-Hydroxy-β-phenylethylamine | Generator | b-(4-Hydroxyphenyl)ethylamine | Generator | Β-(4-hydroxyphenyl)ethylamine | Generator | 2-(4'-Hydroxyphenyl)ethylamine | HMDB | 2-(4-Hydroxyphenyl)ethylamine | HMDB | 4-(2-Aminoethyl)-phenol | HMDB | 4-(2-Aminoethyl)-phenol(thyramin) | HMDB | 4-(2-Aminoethyl)phenol | HMDB | 4-Hydroxy-benzeneethanamine | HMDB | a-(4-Hydroxyphenyl)-b-aminoethane | HMDB | alpha-(4-Hydroxyphenyl)-beta-aminoethane | HMDB | p-(2-Aminoethyl)-phenol | HMDB | p-beta-Aminoethylphenol | HMDB | p-Hydroxy-b-phenethylamine | HMDB | p-Hydroxy-b-phenylethylamine | HMDB | p-Hydroxy-beta-phenethylamine | HMDB | p-Hydroxy-beta-phenylethylamine | HMDB | Systogene | HMDB | Tenosin-wirkstoff | HMDB | Tocosine | HMDB | Tyramine base | HMDB | Tyrosamine | HMDB | Uteramine | HMDB | Para-tyramine | HMDB | 4 Hydroxyphenethylamine | HMDB | 2-(4-Hydroxyphenyl)ethanamine | HMDB | 2-(4’-hydroxyphenyl)ethylamine | HMDB | p-Hydroxy-β-phenylethylamine | HMDB | p-Β-aminoethylphenol | HMDB | Α-(4-hydroxyphenyl)-β-aminoethane | HMDB | 4- (2-Aminoethyl)-phenol | HMDB | 4-(2-Aminoethyl)phenol, 9CI | db_source | 4-hydroxy-Benzeneethanamine | biospider | AEF | biospider | Alpha.-(4-hydroxyphenyl)-beta-aminoethane | HMDB | Beta-hydroxyphenylethylamine | biospider | L-tyramine | biospider | p-(2-aminoethyl)-Phenol | biospider | P-beta-aminoethylphenol | biospider | P-hydroxy-b-phenethylamine | biospider | P-hydroxy-b-phenylethylamine | biospider | P-hydroxy-beta-phenethylamine | biospider | P-hydroxy-beta-phenylethylamine | biospider | P-hydroxyphenethylamine | biospider | P-hydroxyphenylethylamine | biospider | P-tyramine | biospider | Tyramine | db_source | β-(4-hydroxyphenyl)ethylamine | Generator |
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Predicted Properties | |
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Chemical Formula | C8H11NO |
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IUPAC name | 4-(2-aminoethyl)phenol |
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InChI Identifier | InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2 |
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InChI Key | DZGWFCGJZKJUFP-UHFFFAOYSA-N |
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Isomeric SMILES | NCCC1=CC=C(O)C=C1 |
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Average Molecular Weight | 137.179 |
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Monoisotopic Molecular Weight | 137.084063979 |
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Classification |
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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
- 2-arylethylamine
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Phenol
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- 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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Ontology | No ontology term |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 70.04%; H 8.08%; N 10.21%; O 11.66% | DFC |
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Melting Point | Mp 164-164.5° (161°) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 10.4 mg/mL at 15 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | Not Available | |
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Experimental pKa | pKa2 10.9 (25°) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-053r-9500000000-6deb2b5d214f768ca448 | 2014-09-20 | View Spectrum | GC-MS | Tyramine, 3 TMS, GC-MS Spectrum | splash10-00di-2900000000-273503edc6a220e152b6 | Spectrum | GC-MS | Tyramine, non-derivatized, GC-MS Spectrum | splash10-00di-2900000000-80980d19fa83d4b86f91 | Spectrum | GC-MS | Tyramine, 3 TMS, GC-MS Spectrum | splash10-00di-9700000000-78d2ae48da1eee18358e | Spectrum | GC-MS | Tyramine, non-derivatized, GC-MS Spectrum | splash10-001i-9200000000-50c21473a7d48011358c | Spectrum | GC-MS | Tyramine, non-derivatized, GC-MS Spectrum | splash10-00di-1900000000-9b1000a8978b57919c35 | Spectrum | GC-MS | Tyramine, non-derivatized, GC-MS Spectrum | splash10-00di-2900000000-273503edc6a220e152b6 | Spectrum | GC-MS | Tyramine, non-derivatized, GC-MS Spectrum | splash10-00di-2900000000-80980d19fa83d4b86f91 | Spectrum | GC-MS | Tyramine, non-derivatized, GC-MS Spectrum | splash10-00di-9700000000-78d2ae48da1eee18358e | Spectrum | GC-MS | Tyramine, non-derivatized, GC-MS Spectrum | splash10-00di-2900000000-69892c95ab2778a208b3 | Spectrum | Predicted GC-MS | Tyramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001i-9600000000-1d5276a762318a00832d | Spectrum | Predicted GC-MS | Tyramine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fk9-7900000000-8f3b164f36bc5a4df4d7 | Spectrum | Predicted GC-MS | Tyramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tyramine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tyramine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Tyramine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - , negative | splash10-000i-0900000000-066947a256844eb6cbdc | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-000i-0900000000-4b0f190d7304f2cec82d | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-2feedb2abf4fe5413452 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-052r-0900000000-e67940e0a4f0f1b565c4 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00lr-9400000000-47a2e802a22167ed8a63 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00di-0900000000-3229081a448a277191a2 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004l-9300000000-e2fc12d41e4c40a9a296 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-004i-9000000000-92f0b12d0a64443cede8 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (Unknown) , Positive | splash10-001i-9200000000-50c21473a7d48011358c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-0900000000-d7e9a8705227b4504c5c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0006-9000000000-3f02b334907c40a8315c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-0900000000-e98b3afc6fad78d45d38 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-001i-0900000000-54239e66d89de3096ca8 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0079-0902000000-f09759fc06ef461f3aa5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0006-9000000000-9ffe6ee0ce68182216f7 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-0900000000-020a5decfb44fc4f97df | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-004i-0930000000-32ccc375e75dbab3195c | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-00di-0900000000-51c6cc08017f1672b791 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-00di-1900000000-55c25dd64462c06c5316 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-0f96-9500000000-83a70aec6da00b51a6df | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-004i-9100000000-5f044e831c0d2db255fa | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-004i-9000000000-99edae3913507430bf9f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-00di-4900000000-8944003750ac547c2024 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-0900000000-00e85becc8cfc59bdb10 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-0900000000-58e8539844dcdbc977cc | 2017-09-14 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 5408 |
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ChEMBL ID | CHEMBL11608 |
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KEGG Compound ID | C00483 |
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Pubchem Compound ID | 5610 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15760 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00306 |
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CRC / DFC (Dictionary of Food Compounds) ID | BCB62-V:BCB62-V |
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EAFUS ID | 3788 |
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Dr. Duke ID | TYRAMINE |
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BIGG ID | 35110 |
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KNApSAcK ID | C00001435 |
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HET ID | AEF |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1051461 |
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SuperScent ID | Not Available |
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Wikipedia ID | Tyramine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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adrenergic | 37962 | Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter. | DUKE | anti aggregant | | | DUKE | cardiovascular | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | hypertensive | | | DUKE | insectifuge | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | DUKE | neurotoxic | 50910 | A poison that interferes with the functions of the nervous system. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | sympathomimetic | 35524 | A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. | DUKE | vasoconstrictor | 50514 | Drug used to cause constriction of the blood vessels. | DUKE | vasopressor | | | DUKE | anti cholinesterase | 37733 | An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8). | CHEBI | neurotransmitter | 25512 | An endogenous compound that is used to transmit information across the synapse between a neuron and another cell. | CHEBI |
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Enzymes | Name | Gene Name | UniProt ID |
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Aromatic-L-amino-acid decarboxylase | DDC | P20711 | Alpha-2A adrenergic receptor | ADRA2A | P08913 | Alpha-2B adrenergic receptor | ADRA2B | P18089 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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mild |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| meaty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| dirty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| cooked |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| phenolic |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| rubbery |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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