TYRAMINE

Investigational

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325 | Milne, G.W.A. (2017) Drugs: Synonyms and Properties, retrieved from: https://books.google.ru/books?id=RlM8DwAAQBAJ | Grant, W.M & Schuman, J.S. (1993) TOXICOLOGY OF THE EYE, v.1, page 1481, retrieved from: https://books.google.ru/books?id=mDLYCQAAQBAJ | Vardanyan, R. & Hruby, V. (2006) Synthesis of Essential Drugs, page 155, retrieved from: https://books.google.ru/books?id=Jjc7KYWZdOYC

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Trace amine-associated receptor 1 48 Target ID: CHEMBL5857 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325	Agonist 2752	0.2 µM [EC50]
Trace amine-associated receptor 2 10 Target ID: Q9P1P5 Gene ID: 9287.0 Gene Symbol: TAAR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325	Agonist 2752	0.52 nM [EC50]
Dimethylaniline monooxygenase [N-oxide-forming] 3 2 Target ID: P31513 Gene ID: 2328.0 Gene Symbol: FMO3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15922018	Substrate 661
Adrenergic receptor alpha 65 Target ID: CHEMBL2095203 Sources: Milne, G.W.A. (2017) Drugs: Synonyms and Properties, retrieved from: https://books.google.ru/books?id=RlM8DwAAQBAJ	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Open-angle glaucoma 53 Sources: Grant, W.M & Schuman, J.S. (1993) Toxicology of the eye, v.1, page 1481, retrieved from: https://books.google.ru/books?id=mDLYCQAAQBAJ	Primary		Not Provided 511	Unknown Approved Use Unknown
Shock 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16742159	Primary		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Mapping of the distribution of significant proteins and proteoglycans in small intestinal submucosa by fluorescence microscopy.	2001	11853391
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	11299312
Regulation of human monoamine oxidase B gene by Sp1 and Sp3.	2001 Apr	11259630
Involvement of noradrenaline transporters in S-nitrosocysteine-stimulated noradrenaline release from rat brain slices: existence of functional Na(+)-independent transporter activity.	2001 Apr	11137627
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	11322694
Vascular and nociceptive effects of localized prolonged sympathetic blockade in human skin.	2001 Apr 12	11474550
Cloning, sequence analysis, and characterization of the astA gene encoding an arylsulfate sulfotransferase from Citrobacter freundii.	2001 Aug	11534764
Cloning, sequencing and mutagenesis of the genes for aromatic amine dehydrogenase from Alcaligenes faecalis and evolution of amine dehydrogenases.	2001 Aug	11495996
Functional expression of a locust tyramine receptor in murine erythroleukaemia cells.	2001 Dec	11903623
Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor.	2001 Dec	11723224
Biochemical and kinetic analysis of the RNase active sites of the integrase/tyrosine family site-specific DNA recombinases.	2001 Dec 7	11585826
Octopamine influences division of labor in honey bee colonies.	2001 Feb	11318378
Biogenic amines in vacuum-packaged and carbon dioxide-controlled atmosphere-packaged fresh pork stored at -1.50 degrees C.	2001 Feb	11271771
An in situ hybridization protocol to detect rare mRNA expressed in neural tissue using biotin-labelled oligonucleotide probes.	2001 Feb	11223418
Dopamine beta-hydroxylase inactivation generates a protein-bound quinone derivative.	2001 Feb 23	11226418
Evidence for receptor-mediated hepatic uptake of pullulan in rats.	2001 Feb 23	11182206
Nitric oxide induces hydroxyl radical generation in rat hearts via depolarization-induced nitric oxide synthase activation.	2001 Jul	11485040
Formation of biogenic amines in bulk-stored chilled hake (Merluccius merluccius L.) packed under atmospheres.	2001 Jul	11456190
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	11438620
Trace amines: identification of a family of mammalian G protein-coupled receptors.	2001 Jul 31	11459929
Quantitative determination of liriodenine and moupinamide in five species of Mollinedia by high performance liquid chromatography.	2001 Jul-Aug	11708299
[The content of biogenic amines in canned fish from the Turkish market].	2001 Jul-Aug	11505795
Detection of protein oxidation in endothelial cells by fluorescently labelled tyramine.	2001 Jul-Aug	11433184
Immunocytochemical distribution of nitric oxide synthase in the human corpus cavernosum: an electron microscopical study using the tyramide signal amplification technique.	2001 Jun	11482440
Familial orthostatic tachycardia due to norepinephrine transporter deficiency.	2001 Jun	11458707
Effect of P-glycoprotein modulators on the human extraneuronal monoamine transporter.	2001 Jun 22	11430910
Localization of single-copy T-DNA insertion in transgenic shallots (Allium cepa) by using ultra-sensitive FISH with tyramide signal amplification.	2001 Mar	11319036
L-Tyrosine beta-naphthylamide is a potent competitive inhibitor of tyramine N-(hydroxycinnamoyl)transferase in vitro.	2001 Mar	11281128
Neuroendocrine differentiation in bronchial carcinomas of classic squamous-cell type: an immunohistochemical study of 29 cases applying the tyramide signal amplification technique.	2001 Mar	11277422
The pancreas-specific protein disulphide-isomerase PDIp interacts with a hydroxyaryl group in ligands.	2001 Mar 15	11237859
Phenolamine-dependent adenylyl cyclase activation in Drosophila Schneider 2 cells.	2001 Mar 15	11222942
Synthesis and characterization of immobilized dopamine beta-hydroxylase in membrane-bound and solubilized formats.	2001 Mar 28	11282402
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	11377178
Linezolid, a novel oxazolidinone antibiotic: assessment of monoamine oxidase inhibition using pressor response to oral tyramine.	2001 May	11361052
The role of alpha(1)-adrenoceptors and 5-HT(1A) receptors in the control of the micturition reflex in male anaesthetized rats.	2001 May	11325795
Substituent-dependent, positive and negative modulation of Bombyx mori adenylate cyclase by synthetic octopamine/tyramine analogues.	2001 May	11317330
Assessment of the serotonin and norepinephrine reuptake blocking properties of duloxetine in healthy subjects.	2001 May	11282251
Aqueous chromatography utilizing pH-/temperature-responsive polymer stationary phases to separate ionic bioactive compounds.	2001 May 1	11354486
[Comparative study of catalytic properties of the liver monoamine oxidase from the squid Todarodes pacificus and the Wistar rat].	2001 May-Jun	11605436
[New development of hair examination! The searching of hair for the terminal residual substance of pleasant sensation].	2001 Nov	11905040
Oxidation of phenethylamine derivatives by cytochrome P450 2D6: the issue of substrate protonation in binding and catalysis.	2001 Nov 27	11714275
Molecular and pharmacological properties of insect biogenic amine receptors: lessons from Drosophila melanogaster and Apis mellifera.	2001 Sep	11519073
Evidence for proteolytic activity and biogenic amines production in Lactobacillus curvatus and L. homohiochii.	2001 Sep 1	11529444
Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): insights into the mechanisms of substrate recognition.	2002 Apr	11901210
Applications of enzymatic amplification staining in immunophenotyping hematopoietic cells.	2002 Apr 1	11897560
Modification of capillary electrophoresis capillaries by poly(hydroxyethyl methacrylate), poly(diethylene glycol monomethacrylate) and poly(triethylene glycol monomethacrylate).	2002 Feb	11870760
Lignanamides and nonalkaloidal components of Hyoscyamus niger seeds.	2002 Feb	11858758
Linezolid: its role in the treatment of gram-positive, drug-resistant bacterial infections.	2002 Feb 15	11871684
On-line synthesis utilizing immobilized enzyme reactors based upon immobilized dopamine beta-hydroxylase.	2002 Jan 5	11820290
Cytotoxic, antifouling bromotyramines: a synthetic study on simple marine natural products and Their analogues.	2002 Mar 11	11859011

Patents

Sample Use Guides

In Vivo Use Guide

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

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

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Name

Type

Language

TYRAMINE

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)