TYRAMINE

Investigational

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 Search

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

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	Condition	Potency
Trace amine-associated receptor 1 41 Target ID: CHEMBL5857 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325	Agonist 2456		0.200000000000000011 µM [EC50]
Trace amine-associated receptor 2 6 Target ID: Q9P1P5 Gene ID: 9287 Gene Symbol: TAAR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325	Agonist 2456		0.520000000000000018 nM [EC50]
Dimethylaniline monooxygenase [N-oxide-forming] 3 2 Target ID: P31513 Gene ID: 2328 Gene Symbol: FMO3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15922018	Substrate 609
Adrenergic receptor alpha 72 Target ID: CHEMBL2095203 Sources: Milne, G.W.A. (2017) Drugs: Synonyms and Properties, retrieved from: https://books.google.ru/books?id=RlM8DwAAQBAJ	Agonist 2456	Open-angle glaucoma Shock

Conditions

Condition	Modality	Targets	Highest Phase	Product
Open-angle glaucoma 50 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	Adrenergic receptor alpha	Not Provided 523
Shock 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16742159	Primary	Adrenergic receptor alpha	Not Provided 523

PubMed

Title	Date	PubMed
Mapping of the distribution of significant proteins and proteoglycans in small intestinal submucosa by fluorescence microscopy.	2001	11853391
Hydrogen peroxide supports hepatocyte P450 catalysed xenobiotic/drug metabolic activation to form cytotoxic reactive intermediates.	2001	11764944
Quantification of tumour vascularity in squamous cell carcinoma of the tongue using CARD amplification, a systematic sampling technique, and true colour image analysis.	2001	11564894
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
Following the trace of elusive amines.	2001 Aug 14	11504935
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
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	11733992
Biochemical and kinetic analysis of the RNase active sites of the integrase/tyrosine family site-specific DNA recombinases.	2001 Dec 7	11585826
Immunocytochemical localization of acyl-CoA oxidase in the rat central nervous system.	2001 Jan	11577243
Application of gradient-enhanced nuclear Overhauser effect spectroscopy GOESY) in the structure elucidation of plant secondary metabolites.	2001 Jan-Feb	11704958
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
Amino acid-decarboxylase activity of bacteria isolated from fermented pork sausages.	2001 Jun 15	11428577
Effect of P-glycoprotein modulators on the human extraneuronal monoamine transporter.	2001 Jun 22	11430910
[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
Apical dominance in Pssu-ipt-transformed tobacco.	2001 Nov	11684189
Analysis of bacterial vaginosis-related amines in vaginal fluid by gas chromatography and mass spectrometry.	2001 Nov	11682525
A comparison of anti-biotin and biotinylated anti-avidin double-bridge and biotinylated tyramide immunohistochemical amplification.	2001 Nov 15	11640956
Oxidation of phenethylamine derivatives by cytochrome P450 2D6: the issue of substrate protonation in binding and catalysis.	2001 Nov 27	11714275
YUA001, a novel aldose reductase inhibitor isolated from alkalophilic Corynebacterium sp. YUA25. II. Chemical modification and biological activity.	2001 Oct	11776438
Dual action of octopamine on glucose transport into adipocytes: inhibition via beta3-adrenoceptor activation and stimulation via oxidation by amine oxidases.	2001 Oct	11561068
Effect of tail suspension on haemodynamics in intact and sympathectomized rats.	2001 Sep	11606007
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
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	11848564
Prior exposure to lipopolysaccharide potentiates expression of plant defenses in response to bacteria.	2002 Feb	11846881
Effect of noradrenaline on retinal blood flow in healthy subjects.	2002 Feb	11825811
Iron (III) attenuates hydroxyl radical generation accompanying non-enzymatic oxidation of noradrenaline in the rat heart.	2002 Feb	11819034
Linezolid: its role in the treatment of gram-positive, drug-resistant bacterial infections.	2002 Feb 15	11871684
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	11754741
Enzymatic decarboxylation of tyrosine and phenylalanine to enhance volatility for high-precision isotopic analysis.	2002 Jan 15	11817371
Tumor necrosis factor expressed by primary hippocampal neurons and SH-SY5Y cells is regulated by alpha(2)-adrenergic receptor activation.	2002 Jan 15	11782970
On-line synthesis utilizing immobilized enzyme reactors based upon immobilized dopamine beta-hydroxylase.	2002 Jan 5	11820290
Distribution and development of dopamine- and octopamine-synthesizing neurons in the medicinal leech.	2002 Jan 7	11754166
A high-affinity octopamine transporter cloned from the central nervous system of cabbage looper Trichoplusia ni.	2002 Mar 1	11804806
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 `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

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Name

Type

Language

TYRAMINE

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)