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Details

Stereochemistry ACHIRAL
Molecular Formula C8H11NO
Molecular Weight 137.1793
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TYRAMINE

SMILES

c1cc(ccc1CCN)O

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

HIDE SMILES / InChI

Molecular Formula C8H11NO
Molecular Weight 137.1793
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.2 µM [EC50]
Target ID: Q9P1P5
Gene ID: 9287.0
Gene Symbol: TAAR2
Target Organism: Homo sapiens (Human)
0.52 nM [EC50]
Target ID: P31513
Gene ID: 2328.0
Gene Symbol: FMO3
Target Organism: Homo sapiens (Human)
Conditions
PubMed

PubMed

TitleDatePubMed
Association between monoamine oxidase A activity in human male skin fibroblasts and genotype of the MAOA promoter-associated variable number tandem repeat.
1999 Dec
Modulation of gastrin processing by vesicular monoamine transporter type 1 (VMAT1) in rat gastrin cells.
1999 Jun 1
Why do some dietary migraine patients claim they get headaches from placebos?
2000 May
Quantification of tumour vascularity in squamous cell carcinoma of the tongue using CARD amplification, a systematic sampling technique, and true colour image analysis.
2001
Synthesis of monensin derivatives and their effect on the activity of ricin A-chain immunotoxins.
2001
Phenolic constituents from the core of kenaf (Hibiscus cannabinus).
2001 Apr
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
Regulation of human monoamine oxidase B gene by Sp1 and Sp3.
2001 Apr
Involvement of noradrenaline transporters in S-nitrosocysteine-stimulated noradrenaline release from rat brain slices: existence of functional Na(+)-independent transporter activity.
2001 Apr
Effect of fluvastatin, an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase, on nitric oxide-induced hydroxyl radical generation in the rat heart.
2001 Apr 30
Cloning, sequence analysis, and characterization of the astA gene encoding an arylsulfate sulfotransferase from Citrobacter freundii.
2001 Aug
Functional expression of a locust tyramine receptor in murine erythroleukaemia cells.
2001 Dec
An in situ hybridization protocol to detect rare mRNA expressed in neural tissue using biotin-labelled oligonucleotide probes.
2001 Feb
Dopamine beta-hydroxylase inactivation generates a protein-bound quinone derivative.
2001 Feb 23
Evidence for receptor-mediated hepatic uptake of pullulan in rats.
2001 Feb 23
Effects of pH, temperature and NaCl concentration on the growth kinetics, proteolytic activity and biogenic amine production of Enterococcus faecalis.
2001 Feb 28
Purification and characterization of tyrosine decarboxylase of Lactobacillus brevis IOEB 9809 isolated from wine.
2001 Feb 5
Rasagiline [N-propargyl-1R(+)-aminoindan], a selective and potent inhibitor of mitochondrial monoamine oxidase B.
2001 Jan
Formation of nitric oxide from nitroxyl anion: role of quinones and ferricytochrome c.
2001 Jan
Dopamine induces ERK activation in renal epithelial cells through H2O2 produced by monoamine oxidase.
2001 Jan
Dorsomedial medulla is more susceptible than rostral ventrolateral medulla to hypoxic insult in cats.
2001 Jan
The antidepressant-sensitive dopamine transporter in Drosophila melanogaster: a primordial carrier for catecholamines.
2001 Jan
Sensitive nonradioactive detection of mRNA in tissue sections: novel application of the whole-mount in situ hybridization protocol.
2001 Jan
Catecholamine inotropes as growth factors for Staphylococcus epidermidis and other coagulase-negative staphylococci.
2001 Jan 15
Application of gradient-enhanced nuclear Overhauser effect spectroscopy GOESY) in the structure elucidation of plant secondary metabolites.
2001 Jan-Feb
Trace amines: identification of a family of mammalian G protein-coupled receptors.
2001 Jul 31
Detection of protein oxidation in endothelial cells by fluorescently labelled tyramine.
2001 Jul-Aug
Melanocyte-Directed enzyme prodrug therapy (MDEPT): development of second generation prodrugs for targeted treatment of malignant melanoma.
2001 Jun
Localization of single-copy T-DNA insertion in transgenic shallots (Allium cepa) by using ultra-sensitive FISH with tyramide signal amplification.
2001 Mar
L-Tyrosine beta-naphthylamide is a potent competitive inhibitor of tyramine N-(hydroxycinnamoyl)transferase in vitro.
2001 Mar
Neuroendocrine differentiation in bronchial carcinomas of classic squamous-cell type: an immunohistochemical study of 29 cases applying the tyramide signal amplification technique.
2001 Mar
Effectiveness of a Lactobacillus sakei starter culture in the reduction of biogenic amine accumulation as a function of the raw material quality.
2001 Mar
Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms.
2001 Mar
The pancreas-specific protein disulphide-isomerase PDIp interacts with a hydroxyaryl group in ligands.
2001 Mar 15
Phenolamine-dependent adenylyl cyclase activation in Drosophila Schneider 2 cells.
2001 Mar 15
Synthesis and characterization of immobilized dopamine beta-hydroxylase in membrane-bound and solubilized formats.
2001 Mar 28
Neonatal chemical sympathectomy attenuates fructose-induced hypertriglyceridemia and hypertension in rats.
2001 Mar 31
Cloning and sequencing of the astA gene encoding arylsulfate sulfotransferase from Salmonella typhimurium.
2001 May
Assessment of the serotonin and norepinephrine reuptake blocking properties of duloxetine in healthy subjects.
2001 May
Aqueous chromatography utilizing pH-/temperature-responsive polymer stationary phases to separate ionic bioactive compounds.
2001 May 1
Analysis of bacterial vaginosis-related amines in vaginal fluid by gas chromatography and mass spectrometry.
2001 Nov
A comparison of anti-biotin and biotinylated anti-avidin double-bridge and biotinylated tyramide immunohistochemical amplification.
2001 Nov 15
Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): insights into the mechanisms of substrate recognition.
2002 Apr
Enzymatic decarboxylation of tyrosine and phenylalanine to enhance volatility for high-precision isotopic analysis.
2002 Jan 15
Cytotoxic, antifouling bromotyramines: a synthetic study on simple marine natural products and Their analogues.
2002 Mar 11
Patents

Sample Use Guides

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 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 Sat Jun 26 13:47:40 UTC 2021
Edited
by admin
on Sat Jun 26 13:47:40 UTC 2021
Record UNII
X8ZC7V0OX3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TYRAMINE
FHFI   HSDB   MI   VANDF   WHO-DD  
Systematic Name English
TYROSAMINE
Common Name English
TYRAMIN
Systematic Name English
NSC-249188
Code English
RACTOPAMINE HYDROCHLORIDE SUSPENSION IMPURITY, TYRAMINE- [USP]
Common Name English
TOCOSINE
Common Name English
2-P-HYDROXYPHENYLETHYLAMINE
Common Name English
TYRAMINE [WHO-DD]
Common Name English
FEMA NO. 4215
Code English
TYRAMINE [FHFI]
Common Name English
4-HYDROXYPHENETHYLAMINE
Systematic Name English
TYRAMINE [MI]
Common Name English
UTERAMINE
Common Name English
TYRAMINE [VANDF]
Common Name English
TYRAMINE [HSDB]
Common Name English
4-(2-AMINOETHYL)PHENOL
Systematic Name English
SYSTOGENE
Common Name English
Classification Tree Code System Code
DSLD 3158 (Number of products:17)
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
Code System Code Type Description
EVMPD
SUB15650MIG
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
PRIMARY
CAS
51-67-2
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
PRIMARY
WIKIPEDIA
TYRAMINE
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
PRIMARY
MERCK INDEX
M11286
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
200-115-8
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
PRIMARY
RXCUI
10958
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
PRIMARY RxNorm
PUBCHEM
5610
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
PRIMARY
EPA CompTox
51-67-2
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
PRIMARY
DRUG CENTRAL
2784
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
PRIMARY
MESH
D014439
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
PRIMARY
HSDB
2132
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
PRIMARY
FDA UNII
X8ZC7V0OX3
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
PRIMARY
DRUG BANK
DB08841
Created by admin on Sat Jun 26 13:47:41 UTC 2021 , Edited by admin on Sat Jun 26 13:47:41 UTC 2021
PRIMARY
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