Tyramine

Base Information

• Chemical Name: Tyramine
• CAS No.: 51-67-2
• Molecular Formula: C8H11NO
• Molecular Weight: 137.181
• Hs Code.: 29214990
• European Community (EC) Number: 200-115-8
• NSC Number: 249188
• UNII: X8ZC7V0OX3
• DSSTox Substance ID: DTXSID2043874
• Nikkaji Number: J4.123H
• Wikipedia: Tyramine
• Wikidata: Q165930
• Pharos Ligand ID: QNJUTC9Y4RMH
• Metabolomics Workbench ID: 37197
• ChEMBL ID: CHEMBL11608
• Mol file: 51-67-2.mol

Synonyms:4 Hydroxyphenethylamine;4-(2-Aminoethyl)phenol;4-Hydroxyphenethylamine;p-Tyramine;para-Tyramine;Tyramine

Chemical Property of Tyramine

Chemical Property:

• Appearance/Colour: white to light beige solid
• Vapor Pressure: 0.000123mmHg at 25°C
• Melting Point: 155-163 °C
• Refractive Index: 1.5849 (estimate)
• Boiling Point: 325.2 °C at 760 mmHg
• PKA: 9.74(at 25℃)
• Flash Point: 119.2 °C
• PSA: 46.25000
• Density: 1.103 g/cm³
• LogP: 1.59370
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 1g/95mL (15 ºC)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 137.084063974
• Heavy Atom Count: 10
• Complexity: 87.3

Purity/Quality:

99%, ^*data from raw suppliers

p-Tyramine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCN)O
• Recent ClinicalTrials: A Study in Healthy People to Test How Combining BI 1467335 and Tyramine Affects Blood Pressure
• Description: A decarboxylation product of tyrosine found in various fermentation products, including cheeses and some wines. It causes sympathomimetic effects by acting as an indirect agonist, causing the release of endogenous catecholamines. Because it is metabolized principally by monoamine oxidase, patients taking monoamine oxidase inhibitors may have a hypertensive crisis if they ingest foods containing significant amounts of tyramine.
• Uses: adrenergic agonist, vasoconstrictor tyramine is uses as pharmaceutical intermediates. Clinical studies indicate that tyramine has skin-lightening capacities.

Technology Process of Tyramine

There total 69 articles about Tyramine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → tyrosamine (51-67-2)

Guidance literature:

With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase; In various solvent(s); at 30 ℃; for 48h;

Reference yield: 98.0%

N-acetyltyramine (1202-66-0) → tyrosamine (51-67-2)

Guidance literature:

With ammonium bromide; ethylenediamine; at 80 ℃; for 5h; Microwave irradiation; Inert atmosphere; neat (no solvent);

DOI:10.1002/anie.201202354

Reference yield: 87.0%

N-{2-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]ethyl}formamide (1521270-08-5) → tyrosamine (51-67-2)

Guidance literature:

With ethanol; sodium hydroxide; at 78 ℃; for 8h; Reagent/catalyst; Temperature;

DOI:10.2478/s11696-013-0449-y

upstream raw materials:

p-Aminophenethylamine

octopamine

4-cyanomethylphenol

N-<2-(4-hydroxyphenyl)ethyl>benzamide

Downstream raw materials:

N,N-dimethyltyramine

7-hydroxy-1,2,3,4-tetrahydroisoquinoline

6-(4-hydroxy-phenethylamino)-L-gulo-hexanepentol-(1.2.3.4.5)

p-hydroxyphenethyl alcohol

Refernces

• 1、 Zhang, Hongjuan,Lu, Yang,Wu, Siping,Wei, Yu,Liu, Qian,Liu, Junzhong,Jiao, Qingcai. "Two-step enzymatic synthesis of tyramine from raw pyruvate fermentation broth". . p. 38 - 44. Retrieved 2016.
• 2、 Leete et al.. "". . p. 749,754. Retrieved 1952.
• 3、 Chaiyosang, Boonyanoot,Kanokmedhakul, Kwanjai,Kanokmedhakul, Somdej,Laphookhieo, Surat,Phukhatmuen, Piyaporn,Pornpongrungrueng, Pimwadee,Somteds, Apisara,Yahuafai, Jantana. "Cytotoxic and α-glucosidase inhibitory metabolites from twigs and leaves of Phyllanthus mirabilis, a species endemic to limestone mountains". . . Retrieved 2021/12/01.
• 4、 Andexer, Jennifer N.,Cárdenas-Fernández, Max,Hailes, Helen C.,Méndez-Sánchez, Daniel,Richter, Michael,Roddan, Rebecca,Siegrist, Jutta,Subrizi, Fabiana,Thair, Benjamin,Wang, Yu,Ward, John M.. "Multienzyme One-Pot Cascades Incorporating Methyltransferases for the Strategic Diversification of Tetrahydroisoquinoline Alkaloids". supporting information. p. 18673 - 18679. Retrieved 2021/07/19.