60-19-5 Usage
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 60-19-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 0 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 60-19:
(4*6)+(3*0)+(2*1)+(1*9)=35
35 % 10 = 5
So 60-19-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2
60-19-5Relevant articles and documents
Catalytic Strategy for Regioselective Arylethylamine Synthesis
Boyington, Allyson J.,Seath, Ciaran P.,Zearfoss, Avery M.,Xu, Zihao,Jui, Nathan T.
supporting information, p. 4147 - 4153 (2019/03/07)
A mild, modular, and practical catalytic system for the synthesis of the highly privileged phenethylamine pharmacophore is reported. Using a unique combination of organic catalysts to promote the transfer of electrons and hydrogen atoms, this system performs direct hydroarylation of vinyl amine derivatives with a wide range of aryl halides (including aryl chlorides). This general and highly chemoselective protocol delivers a broad range of arylethylamine products with complete regiocontrol. The utility of this process is highlighted by its scalability and the modular synthesis of an array of bioactive small molecules.
Rapid Conventional and Microwave-Assisted Decarboxylation of L-Histidine and Other Amino Acids via Organocatalysis with R-Carvone under Superheated Conditions
Jackson, Douglas M.,Ashley, Robert L.,Brownfield, Callan B.,Morrison, Daniel R.,Morrison, Richard W.
, p. 2691 - 2700 (2015/12/18)
This article reports a new methodology taking advantage of superheated chemistry via either microwave or conventional heating for the facile decarboxylation of alpha amino acids using the recoverable organocatalyst, R-carvone. The decarboxylation of amino acids is an important synthetic route to biologically active amines, and traditional methods of amino acid decarboxylation are time consuming (taking up to several days in the case of L-histidine), are narrow in scope, and make use of toxic catalysts. Decarboxylations of amino acids including L-histidine occur in just minutes while replacing toxic catalysts with green catalyst, spearmint oil. Yields are comparable to or exceed previous methods and purification of product ammonium chloride salts is aided by an isomerization reaction of residual catalyst to phenolic carvacrol. The method has been shown to be effective for the decarboxylations of a range of natural, synthetic, and protected amino acids.
The first total synthesis of aplysamine 6, an inhibitor of isoprenylcysteine carboxy methyltransferase
Ullah, Nisar,Arafeh, Khaled M.
scheme or table, p. 158 - 160 (2009/04/14)
The first total synthesis of aplysamine 6, an inhibitor of isoprenylcysteine carboxy methyltransferase (Icmt), was accomplished in an overall high yielding reaction sequence.
