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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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 47	Agonist 2,678	0.2 µM [EC50]
Trace amine-associated receptor 2 10	Agonist 2,678	0.52 nM [EC50]
Dimethylaniline monooxygenase [N-oxide-forming] 3 2	Substrate 661
Adrenergic receptor alpha 64	Agonist 2,678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Open-angle glaucoma 51	Primary		Not Provided 504	Unknown
Shock 9	Primary		Not Provided 504	Unknown

PubMed

Show entries

Title	Date	PubMed
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
Regulation of human monoamine oxidase B gene by Sp1 and Sp3.	2001 Apr	11259630
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
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

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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.