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	Potency
Trace amine-associated receptor 1 41 Target ID: CHEMBL5857 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325	Agonist 2451	0.2 µM [EC50]
Trace amine-associated receptor 2 6 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 2451	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 608
Adrenergic receptor alpha 71 Target ID: CHEMBL2095203 Sources: Milne, G.W.A. (2017) Drugs: Synonyms and Properties, retrieved from: https://books.google.ru/books?id=RlM8DwAAQBAJ	Agonist 2451

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		Not Provided 523	Unknown Approved Use Unknown
Shock 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16742159	Primary		Not Provided 523	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Association between monoamine oxidase A activity in human male skin fibroblasts and genotype of the MAOA promoter-associated variable number tandem repeat.	1999 Dec	10647887
Modulation of gastrin processing by vesicular monoamine transporter type 1 (VMAT1) in rat gastrin cells.	1999 Jun 1	10332097
Why do some dietary migraine patients claim they get headaches from placebos?	2000 May	10792367
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
Synthesis of monensin derivatives and their effect on the activity of ricin A-chain immunotoxins.	2001	11217376
Phenolic constituents from the core of kenaf (Hibiscus cannabinus).	2001 Apr	11314965
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 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	11335104
Cloning, sequence analysis, and characterization of the astA gene encoding an arylsulfate sulfotransferase from Citrobacter freundii.	2001 Aug	11534764
Functional expression of a locust tyramine receptor in murine erythroleukaemia cells.	2001 Dec	11903623
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
Effects of pH, temperature and NaCl concentration on the growth kinetics, proteolytic activity and biogenic amine production of Enterococcus faecalis.	2001 Feb 28	11252492
Purification and characterization of tyrosine decarboxylase of Lactobacillus brevis IOEB 9809 isolated from wine.	2001 Feb 5	11167003
Rasagiline [N-propargyl-1R(+)-aminoindan], a selective and potent inhibitor of mitochondrial monoamine oxidase B.	2001 Jan	11159700
Formation of nitric oxide from nitroxyl anion: role of quinones and ferricytochrome c.	2001 Jan	11156574
Dopamine induces ERK activation in renal epithelial cells through H2O2 produced by monoamine oxidase.	2001 Jan	11135060
Dorsomedial medulla is more susceptible than rostral ventrolateral medulla to hypoxic insult in cats.	2001 Jan	11133917
The antidepressant-sensitive dopamine transporter in Drosophila melanogaster: a primordial carrier for catecholamines.	2001 Jan	11125028
Sensitive nonradioactive detection of mRNA in tissue sections: novel application of the whole-mount in situ hybridization protocol.	2001 Jan	11118473
Catecholamine inotropes as growth factors for Staphylococcus epidermidis and other coagulase-negative staphylococci.	2001 Jan 15	11164302
Application of gradient-enhanced nuclear Overhauser effect spectroscopy GOESY) in the structure elucidation of plant secondary metabolites.	2001 Jan-Feb	11704958
Trace amines: identification of a family of mammalian G protein-coupled receptors.	2001 Jul 31	11459929
Detection of protein oxidation in endothelial cells by fluorescently labelled tyramine.	2001 Jul-Aug	11433184
Melanocyte-Directed enzyme prodrug therapy (MDEPT): development of second generation prodrugs for targeted treatment of malignant melanoma.	2001 Jun	11408174
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
Effectiveness of a Lactobacillus sakei starter culture in the reduction of biogenic amine accumulation as a function of the raw material quality.	2001 Mar	11252481
Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms.	2001 Mar	11181495
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
Neonatal chemical sympathectomy attenuates fructose-induced hypertriglyceridemia and hypertension in rats.	2001 Mar 31	11403517
Cloning and sequencing of the astA gene encoding arylsulfate sulfotransferase from Salmonella typhimurium.	2001 May	11379783
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
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
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
Enzymatic decarboxylation of tyrosine and phenylalanine to enhance volatility for high-precision isotopic analysis.	2002 Jan 15	11817371
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)