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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
0.200000000000000011 µM [EC50]
Target ID: Q9P1P5
Gene ID: 9287
Gene Symbol: TAAR2
Target Organism: Homo sapiens (Human)
0.520000000000000018 nM [EC50]
Target ID: P31513
Gene ID: 2328
Gene Symbol: FMO3
Target Organism: Homo sapiens (Human)
Conditions
PubMed

PubMed

TitleDatePubMed
Mapping of the distribution of significant proteins and proteoglycans in small intestinal submucosa by fluorescence microscopy.
2001
Hydrogen peroxide supports hepatocyte P450 catalysed xenobiotic/drug metabolic activation to form cytotoxic reactive intermediates.
2001
Quantification of tumour vascularity in squamous cell carcinoma of the tongue using CARD amplification, a systematic sampling technique, and true colour image analysis.
2001
Vascular and nociceptive effects of localized prolonged sympathetic blockade in human skin.
2001 Apr 12
Cloning, sequence analysis, and characterization of the astA gene encoding an arylsulfate sulfotransferase from Citrobacter freundii.
2001 Aug
Cloning, sequencing and mutagenesis of the genes for aromatic amine dehydrogenase from Alcaligenes faecalis and evolution of amine dehydrogenases.
2001 Aug
Following the trace of elusive amines.
2001 Aug 14
Functional expression of a locust tyramine receptor in murine erythroleukaemia cells.
2001 Dec
Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor.
2001 Dec
DNA recombination and RNA cleavage activities of the Flp protein: roles of two histidine residues in the orientation and activation of the nucleophile for strand cleavage.
2001 Dec 7
Biochemical and kinetic analysis of the RNase active sites of the integrase/tyrosine family site-specific DNA recombinases.
2001 Dec 7
Immunocytochemical localization of acyl-CoA oxidase in the rat central nervous system.
2001 Jan
Application of gradient-enhanced nuclear Overhauser effect spectroscopy GOESY) in the structure elucidation of plant secondary metabolites.
2001 Jan-Feb
Nitric oxide induces hydroxyl radical generation in rat hearts via depolarization-induced nitric oxide synthase activation.
2001 Jul
Formation of biogenic amines in bulk-stored chilled hake (Merluccius merluccius L.) packed under atmospheres.
2001 Jul
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
Trace amines: identification of a family of mammalian G protein-coupled receptors.
2001 Jul 31
Quantitative determination of liriodenine and moupinamide in five species of Mollinedia by high performance liquid chromatography.
2001 Jul-Aug
[The content of biogenic amines in canned fish from the Turkish market].
2001 Jul-Aug
Detection of protein oxidation in endothelial cells by fluorescently labelled tyramine.
2001 Jul-Aug
Immunocytochemical distribution of nitric oxide synthase in the human corpus cavernosum: an electron microscopical study using the tyramide signal amplification technique.
2001 Jun
Familial orthostatic tachycardia due to norepinephrine transporter deficiency.
2001 Jun
Amino acid-decarboxylase activity of bacteria isolated from fermented pork sausages.
2001 Jun 15
Effect of P-glycoprotein modulators on the human extraneuronal monoamine transporter.
2001 Jun 22
[Comparative study of catalytic properties of the liver monoamine oxidase from the squid Todarodes pacificus and the Wistar rat].
2001 May-Jun
[New development of hair examination! The searching of hair for the terminal residual substance of pleasant sensation].
2001 Nov
Apical dominance in Pssu-ipt-transformed tobacco.
2001 Nov
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
Oxidation of phenethylamine derivatives by cytochrome P450 2D6: the issue of substrate protonation in binding and catalysis.
2001 Nov 27
YUA001, a novel aldose reductase inhibitor isolated from alkalophilic Corynebacterium sp. YUA25. II. Chemical modification and biological activity.
2001 Oct
Dual action of octopamine on glucose transport into adipocytes: inhibition via beta3-adrenoceptor activation and stimulation via oxidation by amine oxidases.
2001 Oct
Effect of tail suspension on haemodynamics in intact and sympathectomized rats.
2001 Sep
Evidence for proteolytic activity and biogenic amines production in Lactobacillus curvatus and L. homohiochii.
2001 Sep 1
Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): insights into the mechanisms of substrate recognition.
2002 Apr
Applications of enzymatic amplification staining in immunophenotyping hematopoietic cells.
2002 Apr 1
Modification of capillary electrophoresis capillaries by poly(hydroxyethyl methacrylate), poly(diethylene glycol monomethacrylate) and poly(triethylene glycol monomethacrylate).
2002 Feb
Lignanamides and nonalkaloidal components of Hyoscyamus niger seeds.
2002 Feb
Growth of Carnobacterium divergens V41 and production of biogenic amines and divercin V41 in sterile cold-smoked salmon extract at varying temperatures, NaCl levels, and glucose concentrations.
2002 Feb
Prior exposure to lipopolysaccharide potentiates expression of plant defenses in response to bacteria.
2002 Feb
Effect of noradrenaline on retinal blood flow in healthy subjects.
2002 Feb
Iron (III) attenuates hydroxyl radical generation accompanying non-enzymatic oxidation of noradrenaline in the rat heart.
2002 Feb
Linezolid: its role in the treatment of gram-positive, drug-resistant bacterial infections.
2002 Feb 15
Tyrosine residues near the FAD binding site are critical for FAD binding and for the maintenance of the stable and active conformation of rat monoamine oxidase A.
2002 Jan
Enzymatic decarboxylation of tyrosine and phenylalanine to enhance volatility for high-precision isotopic analysis.
2002 Jan 15
Tumor necrosis factor expressed by primary hippocampal neurons and SH-SY5Y cells is regulated by alpha(2)-adrenergic receptor activation.
2002 Jan 15
On-line synthesis utilizing immobilized enzyme reactors based upon immobilized dopamine beta-hydroxylase.
2002 Jan 5
Distribution and development of dopamine- and octopamine-synthesizing neurons in the medicinal leech.
2002 Jan 7
A high-affinity octopamine transporter cloned from the central nervous system of cabbage looper Trichoplusia ni.
2002 Mar 1
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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