U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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
Structure of TYRAMINE

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

HIDE SMILES / InChI

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.

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
Mapping of the distribution of significant proteins and proteoglycans in small intestinal submucosa by fluorescence microscopy.
2001
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 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
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
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
Biochemical and kinetic analysis of the RNase active sites of the integrase/tyrosine family site-specific DNA recombinases.
2001 Dec 7
Octopamine influences division of labor in honey bee colonies.
2001 Feb
Biogenic amines in vacuum-packaged and carbon dioxide-controlled atmosphere-packaged fresh pork stored at -1.50 degrees C.
2001 Feb
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
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
Effect of P-glycoprotein modulators on the human extraneuronal monoamine transporter.
2001 Jun 22
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
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
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
Linezolid, a novel oxazolidinone antibiotic: assessment of monoamine oxidase inhibition using pressor response to oral tyramine.
2001 May
The role of alpha(1)-adrenoceptors and 5-HT(1A) receptors in the control of the micturition reflex in male anaesthetized rats.
2001 May
Substituent-dependent, positive and negative modulation of Bombyx mori adenylate cyclase by synthetic octopamine/tyramine analogues.
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
[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
Oxidation of phenethylamine derivatives by cytochrome P450 2D6: the issue of substrate protonation in binding and catalysis.
2001 Nov 27
Molecular and pharmacological properties of insect biogenic amine receptors: lessons from Drosophila melanogaster and Apis mellifera.
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
Linezolid: its role in the treatment of gram-positive, drug-resistant bacterial infections.
2002 Feb 15
On-line synthesis utilizing immobilized enzyme reactors based upon immobilized dopamine beta-hydroxylase.
2002 Jan 5
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 Mon Mar 31 17:50:00 GMT 2025
Edited
by admin
on Mon Mar 31 17:50:00 GMT 2025
Record UNII
X8ZC7V0OX3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TYRAMINE
FHFI   HSDB   MI   VANDF   WHO-DD  
Systematic Name English
FEMA NO. 4215
Preferred Name English
RACTOPAMINE HYDROCHLORIDE SUSPENSION IMPURITY, TYRAMINE- [USP IMPURITY]
Common Name English
TYROSAMINE
Common Name English
TYRAMIN
Systematic Name English
NSC-249188
Code English
TOCOSINE
Common Name English
2-P-HYDROXYPHENYLETHYLAMINE
Common Name 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
Tyramine [WHO-DD]
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 Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
Code System Code Type Description
EVMPD
SUB15650MIG
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
CHEBI
15760
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
SMS_ID
100000077310
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
CAS
51-67-2
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
WIKIPEDIA
TYRAMINE
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
MERCK INDEX
m11286
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
200-115-8
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
RXCUI
10958
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY RxNorm
PUBCHEM
5610
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
CHEBI
327995
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
EPA CompTox
DTXSID2043874
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
NSC
249188
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
DRUG CENTRAL
2784
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
JECFA MONOGRAPH
1580
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
MESH
D014439
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
HSDB
2132
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
DAILYMED
X8ZC7V0OX3
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
FDA UNII
X8ZC7V0OX3
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
DRUG BANK
DB08841
Created by admin on Mon Mar 31 17:50:00 GMT 2025 , Edited by admin on Mon Mar 31 17:50:00 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
TRANSPORTER -> SUBSTRATE
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
PARENT -> METABOLITE
PARENT -> METABOLITE
METABOLITE -> PARENT
METABOLITE ACTIVE -> PARENT
MINOR
Related Record Type Details
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY