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T2879

Sigma-Aldrich

Tyramine hydrochloride

≥98%

Synonym(s):

4-(2-Aminoethyl)phenol hydrochloride, 4-Hydroxyphenethylamine hydrochloride, Tyrosamine hydrochloride

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About This Item

Linear Formula:
HOC6H4CH2CH2NH2 · HCl
CAS Number:
60-19-5
Molecular Weight:
173.64
Beilstein/REAXYS Number:
3627058
EC Number:
200-462-5
MDL number:
MFCD00012901
UNSPSC Code:
12352116
PubChem Substance ID:
24277896
NACRES:
NA.77

Quality Level

200

assay

≥98%

mp

271-274 °C (lit.)

solubility

H2O: soluble 50 mg/ml, clear, colorless to faintly yellow

SMILES string

Cl[H].NCCc1ccc(O)cc1

InChI

1S/C8H11NO.ClH/c9-6-5-7-1-3-8(10)4-2-7;/h1-4,10H,5-6,9H2;1H

InChI key

RNISDHSYKZAWOK-UHFFFAOYSA-N

Gene Information

human ... ADORA2A(135) , ADORA2B(136) , ADORA3(140)

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Application

Tyramine hydrochloride has been:
  • coinfused with adenosine in control subjects and patients in order to reduce leg blood flow by 50% without affecting arterial blood pressure
  • labelled with fluorescence dyes (Atto 488 and Atto 655) to serve as a substrate for peroxidase in immunofluorescence analysis
  • used in dimethylformamide, labelled with 5-(and-6)carboxyfluorescein, succinimidyl ester/biotin to serve as a substrate for peroxidase in tyramide signal amplification

Biochem/physiol Actions

Tyramine is a biogenic amine and a neuromodulator localized to the nervous system. Tyrosine decarboxylase catalysis the formation of tyramine from tyrosine. Tyramine is found to be associated with a number of psychiatric disorders. Tyramine ingestion depletes serotonin, epinephrine and norepinephrine reserves. This results in elevated biological events such as cardiovascular function, blood pressure, glucose production and overall metabolism. It also causes depression, migraine and insomnia. Tyramine is present is several food sources. The process of food fermentation and spoilage increases its tyramine content.
Can enter catecholaminergic terminals and be released as a false transmitter.

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Storage Class

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wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Immunostaining Enhancement
Immunohistochemistry: Basics and Methods, 47-59 (2009)
Two functional but noncomplementing Drosophila tyrosine decarboxylase genes distinct roles for neural tyramine and octopamine in female fertility
Cole Shannon H, et al.
Test, 280(15), 14948-14955 (2005)
Urocortin and corticotropin-releasing factor receptor 2 in human renal cell carcinoma: disruption of an endogenous inhibitor of angiogenesis and proliferation
Tezval Hossein, et al.
World Journal of Urology, 27(6), 825-825 (2009)
A trace amine, tyramine, functions as a neuromodulator in Drosophila melanogaster
Nagaya Y, et al.
Neuroscience Letters, 329(3), 324-328 (2002)
Pia Thaning et al.
Diabetes care, 34(5), 1186-1191 (2011-03-31)
Sympathetic vasoconstriction is blunted in contracting human skeletal muscles (functional sympatholysis). In young subjects, infusion of adenosine and ATP increases blood flow, and the latter compound also attenuates α-adrenergic vasoconstriction. In patients with type 2 diabetes and age-matched healthy subjects
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