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T90344

Sigma-Aldrich

Tyramine

≥98.0%

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Synonym(s):
2-(4-Hydroxyphenyl)ethylamine, 4-(2-Aminoethyl)phenol, 4-Hydroxyphenethylamine
Linear Formula:
HOC6H4CH2CH2NH2
CAS Number:
Molecular Weight:
137.18
Beilstein:
1099914
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥98.0%

bp

175-181 °C/8 mmHg (lit.)

mp

160-162 °C (lit.)

SMILES string

NCCc1ccc(O)cc1

InChI

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

InChI key

DZGWFCGJZKJUFP-UHFFFAOYSA-N

Gene Information

rat ... Drd2(24318)

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Related Categories

Application

  • Tyramine is extensively used in the preparation of a variety of hydrogels for biomedical applications.
  • It is used as a key precursor in the total synthesis of (−)-mesembrine and (−)-galanthamine.
  • It can also be used in the preparation of tyramine-functionalized graphene quantum dots (GQDs) as fluorescence reporters for optical sensing of metabolites.

Biochem/physiol Actions

Can enter catecholaminergic terminals and be released as a false transmitter.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Ultrasensitive profiling of metabolites using tyramine-functionalized graphene quantum dots.
Li N, et al.
ACS Nano, 10(3), 3622-3629 (2016)
Total Synthesis of (−)-Galanthamine by Remote Asymmetric Induction.
Kodama, Sumiaki et al.
Angewandte Chemie (International Edition in English), 43(20), 2659-2661 (2004)
Simona Distinto et al.
European journal of medicinal chemistry, 48, 284-295 (2012-01-10)
Monoamine oxidase B (MAO-B) is a promising target for the treatment of neurodegenerative disorders. We report the synthesis and the biological evaluation of halogenated derivatives of 1-aryliden-2-(4-phenylthiazol-2-yl)hydrazines. The fluorinated series shows interesting activity and great selectivity toward the human recombinant
In situ forming hydrogels based on tyramine conjugated 4-Arm-PPO-PEO via enzymatic oxidative reaction.
Park KM, et al.
Biomacromolecules, 11(3), 706-712 (2010)
Enzyme-mediated fast in situ formation of hydrogels from dextran-tyramine conjugates.
Jin R, et al.
Biomaterials, 28(18), 2791-2800 (2007)

Protocols

HPLC Analysis of Biogenic Amines on Ascentis® RP-Amide

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