Tyramine hydrochloride Chemical Properties

Melting point:

253-255 °C(lit.)

Boiling point:

269°C/760mmHg

storage temp. 

Store below +30°C.

solubility 

H2O: soluble50 mg/ml, clear, colorless to faintly yellow

form 

Crystalline Powder

color 

White to almost white

PH

<7 (H2O)

Sensitive 

Hygroscopic

Merck 

14,9835

BRN 

3627058

Stability:

Hygroscopic

LogP

0.722 (est)

CAS DataBase Reference

60-19-5(CAS DataBase Reference)

EPA Substance Registry System

Phenol, 4-(2-aminoethyl)-, hydrochloride (60-19-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

NL4375000

F 

3-8-10

TSCA 

Yes

HS Code 

29222900

MSDS

• Language:English Provider:4-Hydroxyphenethylamine hydrochloride
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Tyramine hydrochloride Usage And Synthesis

Chemical Properties

Off-White to Light Yellow Powder

Occurrence

Tyramine was originally a compound isolated from ergot alkaloids and decaying animal tissue. It has pharmacological effects such as increasing blood pressure and exciting the uterus.

Uses

Tyramine hydrochloride is a sympathomimetic, the hydrochloride salt of the naturally-occurring monoamine derived from the amino acid tyrosine. Tyramine acts as a catecholamine releasing agent but cannot cross the blood-brain barrier. Tyramine hydrochloride is an amino acid that helps regulate blood pressure. Tyramine hydrochloride occurs naturally in the body, and it's found in certain foods.

Application

Tyramine hydrochloride (T-HCl) is a kind of fluorogenic substrate of peroxidase. It is a naturally occurring monoamine derived from tyrosine. Tyramine Hydrochloride has been used:
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.
Neurotransmitter.

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.

Synthesis

Tyramine [2-(p-hydroxyphenyl) ethylamine], a significant metabolite of tyrosine, enzymatic synthesis of tyramine was established by two-step biocatalytic reaction. Firstly, l-tyrosine was prepared from raw pyruvate fermentation broth under the catalysis of TPL. Pyruvate fermentation broth was simply centrifuged, and then the supernatant was diluted and used as substrate to produce l-tyrosine. Secondly, l-tyrosine was collected as starting material to synthesize tyramine by immobilized TDC cells from Lactobacillus brevis. Pyridoxal phosphate was the common coenzyme for these two enzymes.

Purification Methods

Crystallise the hydrochloride from EtOH by addition of diethyl ether, or from conc HCl. [Beilstein 3 II 355.]

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