Tyramine
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Basic Info
| Common Name | Tyramine(F05376) |
| 2D Structure | |
| Description | Tyramine is a monoamine compound derived from the amino acid tyrosine. 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, chocolate, alcoholic beverages, cheese, soy sauce, sauerkraut, and processed meat. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more. Tyramine acts as a neurotransmitter via a G protein-coupled receptor with high affinity for tyramine called TA1. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. An indirect sympathomimetic, Tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase so it prolongs the actions of adrenergic transmitters. It also provokes transmitter release from adrenergic terminals. |
| FRCD ID | F05376 |
| CAS Number | 51-67-2 |
| PubChem CID | 5610 |
| Formula | C8H11NO |
| IUPAC Name | 4-(2-aminoethyl)phenol |
| InChI Key | DZGWFCGJZKJUFP-UHFFFAOYSA-N |
| InChI | InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2 |
| Canonical SMILES | C1=CC(=CC=C1CCN)O |
| Isomeric SMILES | C1=CC(=CC=C1CCN)O |
| Wikipedia | Tyramine |
| Synonyms |
4-(2-Aminoethyl)phenol
tyramine
51-67-2
4-Hydroxyphenethylamine
p-Tyramine
2-(4-Hydroxyphenyl)ethylamine
Uteramine
Tyramin
Tyrosamine
Tocosine
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Phenethylamines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenethylamines |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as phenethylamines. These are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 137.182 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Complexity | 87.3 |
| Monoisotopic Mass | 137.084 |
| Exact Mass | 137.084 |
| XLogP | 1.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.5077 |
| Human Intestinal Absorption | HIA+ | 0.9865 |
| Caco-2 Permeability | Caco2+ | 0.6439 |
| P-glycoprotein Substrate | Non-substrate | 0.6248 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9787 |
| Non-inhibitor | 0.9246 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.6182 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5368 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8558 |
| CYP450 2D6 Substrate | Substrate | 0.5417 |
| CYP450 3A4 Substrate | Non-substrate | 0.7499 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9361 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9231 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9044 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8495 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7840 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.6004 |
| Non-inhibitor | 0.7751 | |
| AMES Toxicity | Non AMES toxic | 0.5395 |
| Carcinogens | Non-carcinogens | 0.7823 |
| Fish Toxicity | Low FHMT | 0.8113 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9480 |
| Honey Bee Toxicity | High HBT | 0.5302 |
| Biodegradation | Ready biodegradable | 0.5855 |
| Acute Oral Toxicity | II | 0.6377 |
| Carcinogenicity (Three-class) | Non-required | 0.7249 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.0573 | LogS |
| Caco-2 Permeability | 0.9409 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.3416 | LD50, mol/kg |
| Fish Toxicity | 2.4609 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.5791 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Detection of biogenic amines in pet food ingredients by RP-HPLC with automated dansyl chloride derivatisation. | J Sep Sci | 2018 Oct 14 | 30318732 |
| Safety Evaluations of <i>Bifidobacterium bifidum</i> BGN4 and <i>Bifidobacterium longum</i> BORI. | Int J Mol Sci | 2018 May 9 | 29747442 |
| Safety hazards in bacteriocinogenic Staphylococcus strains isolated from goat and sheep milk. | Microb Pathog | 2018 Mar | 29355699 |
| Mechanisms of the antilipolytic response of human adipocytes to tyramine, a trace amine present in food. | J Physiol Biochem | 2018 Jul 23 | 30039351 |
| Safety assessment and functional properties of four enterococci strains isolated from regional Argentinean cheese. | Int J Food Microbiol | 2018 Jul 20 | 29669304 |
| A study of the tyramine/glucose Maillard reaction: Variables, characterization, cytotoxicity and preliminary application. | Food Chem | 2018 Jan 15 | 28873582 |
| A colorimetric immunoassay based on glucose oxidase-induced AuNP aggregation for the detection of fumonisin B<sub>1</sub>. | Talanta | 2018 Aug 15 | 29784363 |
| Fe(III) conjugated fluorescent organic nanoparticles for ratiometric detection oftyramine in aqueous medium: A novel method to determine food quality. | Food Chem | 2018 Apr 15 | 29287351 |
| [Content and Origin of Nonvolatile Amines in Various Commercial Pickles]. | Shokuhin Eiseigaku Zasshi | 2018 | 29743466 |
| Safety assessment of commensal enterococci from dogs. | Folia Microbiol (Praha) | 2017 Nov | 28316009 |
| Analysis of antimicrobial and immunomodulatory substances produced byheterofermentative Lactobacillus reuteri. | Folia Microbiol (Praha) | 2017 Nov | 28401403 |
| Inactivation and changes in metabolic profile of selected foodborne bacteria by460 nm LED illumination. | Food Microbiol | 2017 May | 28040158 |
| The dietary biogenic amines tyramine and histamine show synergistic toxicity towards intestinal cells in culture. | Food Chem | 2017 Mar 1 | 27719906 |
| In vitro effects of sodium bicarbonate buffer on rumen fermentation, levels of lipopolysaccharide and biogenic amine, and composition of rumen microbiota. | J Sci Food Agric | 2017 Mar | 27339112 |
| Determination of biogenic amines in licorice (Glycyrrhiza glabra) by ion-pairextraction and liquid chromatography-tandem mass spectrometry. | J Sci Food Agric | 2017 Mar | 27381870 |
| Interactive effects of protein and carbohydrates on production of microbialmetabolites in the large intestine of growing pigs. | Arch Anim Nutr | 2017 Jun | 28429993 |
| Rapid discrimination of strain-dependent fermentation characteristics amongLactobacillus strains by NMR-based metabolomics of fermented vegetable juice. | PLoS One | 2017 Jul 31 | 28759594 |
| Identification and Quantification of Potential Anti-inflammatory Hydroxycinnamic Acid Amides from Wolfberry. | J Agric Food Chem | 2017 Jan 18 | 28008757 |
| Tyramine detection using PEDOT:PSS/AuNPs/1-methyl-4-mercaptopyridine modifiedscreen-printed carbon electrode with molecularly imprinted polymer solid phaseextraction. | Biosens Bioelectron | 2017 Jan 15 | 27543858 |
| Effect of a nano-silver coating on the quality of fresh turkey meat duringstorage after modified atmosphere or vacuum packaging. | Poult Sci | 2017 Feb 1 | 27647930 |
Targets
- General Function:
- Potassium channel regulator activity
- Specific Function:
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name:
- DRD2
- Uniprot ID:
- P14416
- Molecular Weight:
- 50618.91 Da
References
- Wilcox RE, Tseng T, Brusniak MY, Ginsburg B, Pearlman RS, Teeter M, DuRand C, Starr S, Neve KA: CoMFA-based prediction of agonist affinities at recombinant D1 vs D2 dopamine receptors. J Med Chem. 1998 Oct 22;41(22):4385-99. [9784114 ]
- General Function:
- G-protein coupled amine receptor activity
- Specific Function:
- Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
- Gene Name:
- DRD1
- Uniprot ID:
- P21728
- Molecular Weight:
- 49292.765 Da
References
- Wilcox RE, Tseng T, Brusniak MY, Ginsburg B, Pearlman RS, Teeter M, DuRand C, Starr S, Neve KA: CoMFA-based prediction of agonist affinities at recombinant D1 vs D2 dopamine receptors. J Med Chem. 1998 Oct 22;41(22):4385-99. [9784114 ]
- General Function:
- Signal transducer activity
- Specific Function:
- Guanine nucleotide-binding proteins (G proteins) are involved as modulators or transducers in various transmembrane signaling systems.
- Gene Name:
- GNA15
- Uniprot ID:
- P30679
- Molecular Weight:
- 43567.615 Da
References
- Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]
- General Function:
- Trace-amine receptor activity
- Specific Function:
- Receptor for trace amines, including beta-phenylethylamine (b-PEA), p-tyramine (p-TYR), octopamine and tryptamine, with highest affinity for b-PEA and p-TYR. Unresponsive to classical biogenic amines, such as epinephrine and histamine and only partially activated by dopamine and serotonine. Trace amines are biogenic amines present in very low levels in mammalian tissues. Although some trace amines have clearly defined roles as neurotransmitters in invertebrates, the extent to which they function as true neurotransmitters in vertebrates has remained speculative. Trace amines are likely to be involved in a variety of physiological functions that have yet to be fully understood. The signal transduced by this receptor is mediated by the G(s)-class of G-proteins which activate adenylate cyclase.
- Gene Name:
- TAAR1
- Uniprot ID:
- Q96RJ0
- Molecular Weight:
- 39091.34 Da
References
- Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]