Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H11NO |
Molecular Weight | 137.179 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCC1=CC=C(O)C=C1
InChI
InChIKey=DZGWFCGJZKJUFP-UHFFFAOYSA-N
InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
Molecular Formula | C8H11NO |
Molecular Weight | 137.179 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Tyramine is a naturally occurring monoamine compound and trace amine derived from the amino acid tyrosine. Tyramine occurs widely in plants and animals, and is metabolized by the enzyme monoamine oxidase. Tyramine is an alpha-adrenergic agonist. Hypertension can occur, from ingestion of tyramine-rich foods in conjunction with monoamine oxidase inhibitors. The possibility that tyramine acts directly as a neurotransmitter was revealed by the discovery of a G protein-coupled receptor with high affinity for tyramine, called TAAR. It exhibits sympathomimetic effects by causing the release of endogenic norepinephrine. It has been used in mydriatic eyedrops. This has been said to reduce the intraocular pressure in rabbits and in some patients with open-angle glaucoma.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5857 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325 |
0.2 µM [EC50] | ||
Target ID: Q9P1P5 Gene ID: 9287.0 Gene Symbol: TAAR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325 |
0.52 nM [EC50] | ||
Target ID: P31513 Gene ID: 2328.0 Gene Symbol: FMO3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15922018 |
|||
Target ID: CHEMBL2095203 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/16742159 |
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Mapping of the distribution of significant proteins and proteoglycans in small intestinal submucosa by fluorescence microscopy. | 2001 |
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Mechanisms of inverse agonism of antipsychotic drugs at the D(2) dopamine receptor: use of a mutant D(2) dopamine receptor that adopts the activated conformation. | 2001 Apr |
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Regulation of human monoamine oxidase B gene by Sp1 and Sp3. | 2001 Apr |
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Involvement of noradrenaline transporters in S-nitrosocysteine-stimulated noradrenaline release from rat brain slices: existence of functional Na(+)-independent transporter activity. | 2001 Apr |
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Effect of the interaction between a low tyramine-producing Lactobacillus and proteolytic staphylococci on biogenic amine production during ripening and storage of dry sausages. | 2001 Apr 11 |
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Vascular and nociceptive effects of localized prolonged sympathetic blockade in human skin. | 2001 Apr 12 |
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Cloning, sequence analysis, and characterization of the astA gene encoding an arylsulfate sulfotransferase from Citrobacter freundii. | 2001 Aug |
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Cloning, sequencing and mutagenesis of the genes for aromatic amine dehydrogenase from Alcaligenes faecalis and evolution of amine dehydrogenases. | 2001 Aug |
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Functional expression of a locust tyramine receptor in murine erythroleukaemia cells. | 2001 Dec |
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Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor. | 2001 Dec |
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Biochemical and kinetic analysis of the RNase active sites of the integrase/tyrosine family site-specific DNA recombinases. | 2001 Dec 7 |
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Octopamine influences division of labor in honey bee colonies. | 2001 Feb |
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Biogenic amines in vacuum-packaged and carbon dioxide-controlled atmosphere-packaged fresh pork stored at -1.50 degrees C. | 2001 Feb |
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An in situ hybridization protocol to detect rare mRNA expressed in neural tissue using biotin-labelled oligonucleotide probes. | 2001 Feb |
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Dopamine beta-hydroxylase inactivation generates a protein-bound quinone derivative. | 2001 Feb 23 |
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Evidence for receptor-mediated hepatic uptake of pullulan in rats. | 2001 Feb 23 |
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Nitric oxide induces hydroxyl radical generation in rat hearts via depolarization-induced nitric oxide synthase activation. | 2001 Jul |
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Formation of biogenic amines in bulk-stored chilled hake (Merluccius merluccius L.) packed under atmospheres. | 2001 Jul |
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Reappearance of cardiac presynaptic sympathetic nerve terminals in the transplanted heart: correlation between PET using (11)C-hydroxyephedrine and invasively measured norepinephrine release. | 2001 Jul |
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Trace amines: identification of a family of mammalian G protein-coupled receptors. | 2001 Jul 31 |
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Quantitative determination of liriodenine and moupinamide in five species of Mollinedia by high performance liquid chromatography. | 2001 Jul-Aug |
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[The content of biogenic amines in canned fish from the Turkish market]. | 2001 Jul-Aug |
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Detection of protein oxidation in endothelial cells by fluorescently labelled tyramine. | 2001 Jul-Aug |
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Immunocytochemical distribution of nitric oxide synthase in the human corpus cavernosum: an electron microscopical study using the tyramide signal amplification technique. | 2001 Jun |
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Familial orthostatic tachycardia due to norepinephrine transporter deficiency. | 2001 Jun |
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Effect of P-glycoprotein modulators on the human extraneuronal monoamine transporter. | 2001 Jun 22 |
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Localization of single-copy T-DNA insertion in transgenic shallots (Allium cepa) by using ultra-sensitive FISH with tyramide signal amplification. | 2001 Mar |
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L-Tyrosine beta-naphthylamide is a potent competitive inhibitor of tyramine N-(hydroxycinnamoyl)transferase in vitro. | 2001 Mar |
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Neuroendocrine differentiation in bronchial carcinomas of classic squamous-cell type: an immunohistochemical study of 29 cases applying the tyramide signal amplification technique. | 2001 Mar |
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The pancreas-specific protein disulphide-isomerase PDIp interacts with a hydroxyaryl group in ligands. | 2001 Mar 15 |
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Phenolamine-dependent adenylyl cyclase activation in Drosophila Schneider 2 cells. | 2001 Mar 15 |
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Synthesis and characterization of immobilized dopamine beta-hydroxylase in membrane-bound and solubilized formats. | 2001 Mar 28 |
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Structure-activity studies leading to (-)1-(benzofuran-2-yl)-2-propylaminopentane, ((-)BPAP), a highly potent, selective enhancer of the impulse propagation mediated release of catecholamines and serotonin in the brain. | 2001 May |
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Linezolid, a novel oxazolidinone antibiotic: assessment of monoamine oxidase inhibition using pressor response to oral tyramine. | 2001 May |
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The role of alpha(1)-adrenoceptors and 5-HT(1A) receptors in the control of the micturition reflex in male anaesthetized rats. | 2001 May |
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Substituent-dependent, positive and negative modulation of Bombyx mori adenylate cyclase by synthetic octopamine/tyramine analogues. | 2001 May |
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Assessment of the serotonin and norepinephrine reuptake blocking properties of duloxetine in healthy subjects. | 2001 May |
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Aqueous chromatography utilizing pH-/temperature-responsive polymer stationary phases to separate ionic bioactive compounds. | 2001 May 1 |
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[Comparative study of catalytic properties of the liver monoamine oxidase from the squid Todarodes pacificus and the Wistar rat]. | 2001 May-Jun |
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[New development of hair examination! The searching of hair for the terminal residual substance of pleasant sensation]. | 2001 Nov |
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Oxidation of phenethylamine derivatives by cytochrome P450 2D6: the issue of substrate protonation in binding and catalysis. | 2001 Nov 27 |
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Molecular and pharmacological properties of insect biogenic amine receptors: lessons from Drosophila melanogaster and Apis mellifera. | 2001 Sep |
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Evidence for proteolytic activity and biogenic amines production in Lactobacillus curvatus and L. homohiochii. | 2001 Sep 1 |
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Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): insights into the mechanisms of substrate recognition. | 2002 Apr |
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Applications of enzymatic amplification staining in immunophenotyping hematopoietic cells. | 2002 Apr 1 |
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Modification of capillary electrophoresis capillaries by poly(hydroxyethyl methacrylate), poly(diethylene glycol monomethacrylate) and poly(triethylene glycol monomethacrylate). | 2002 Feb |
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Lignanamides and nonalkaloidal components of Hyoscyamus niger seeds. | 2002 Feb |
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Linezolid: its role in the treatment of gram-positive, drug-resistant bacterial infections. | 2002 Feb 15 |
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On-line synthesis utilizing immobilized enzyme reactors based upon immobilized dopamine beta-hydroxylase. | 2002 Jan 5 |
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Cytotoxic, antifouling bromotyramines: a synthetic study on simple marine natural products and Their analogues. | 2002 Mar 11 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7356898
1.25 ug, 4.75 ug, 12.5 ug, 47.5 ug, 125 ug, and 475 ug twice weekly with a minimum of 48 h between doses. The six doses were given in ascending order.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12438548
In rat cardiomyocytes, 0.3 mM tyramine activated 2-deoxyglucose uptake to around 40% of the maximal insulin effect and benzylamine had no effect. Concentration-dependent studies showed that the EC50 of tyramine in activating hexose uptake was 10 uM in cardiomyocytes, whereas in the presence of vanadate, the EC50 of tyramine was 117 uM in adipocytes.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:50:00 GMT 2025
by
admin
on
Mon Mar 31 17:50:00 GMT 2025
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Record UNII |
X8ZC7V0OX3
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Record Status |
Validated (UNII)
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Record Version |
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3158 (Number of products:17)
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SUB15650MIG
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TYRAMINE
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m11286
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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TRANSPORTER -> SUBSTRATE |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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Related Record | Type | Details | ||
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PARENT -> METABOLITE |
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PARENT -> METABOLITE |
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METABOLITE -> PARENT |
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METABOLITE ACTIVE -> PARENT |
MINOR
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PARENT -> IMPURITY |
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ACTIVE MOIETY |
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