T90344

Sigma-Aldrich

Tyramine

≥98.0%

Synonym(s):
2-(4-Hydroxyphenyl)ethylamine, 4-Hydroxyphenethylamine, 4-(2-Aminoethyl)phenol
Linear Formula:
HOC6H4CH2CH2NH2
CAS Number:
Molecular Weight:
137.18
Beilstein/REAXYS Number:
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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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.

Packaging

5, 25 g in glass bottle

Biochem/physiol Actions

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

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T90344.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

hazcat

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

Target Organs

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Enzyme-mediated fast in situ formation of hydrogels from dextran-tyramine conjugates.
Jin R, et al.
Biomaterials, 28(18), 2791-2800 (2007)
Desymmetrization of cyclohexadienones via cinchonine derived thiourea-catalyzed enantioselective aza-Michael reaction and total synthesis of (−)-Mesembrine
Gu Q and You S-L
Chemical Science, 2(8), 1519-1522 (2011)
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)
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...
Ultrasensitive profiling of metabolites using tyramine-functionalized graphene quantum dots.
Li N, et al.
ACS Nano, 10(3), 3622-3629 (2016)
Protocols
HPLC Analysis of Biogenic Amines on Ascentis<sup>®</sup> RP-Amide
Read More

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