Hordenine

Hordenine (Item No. 21626) is a naturally occurring alkaloid found in a variety of plants, most commonly germinated barley (Hordeum species) from which the name is derived, and is structurally classified as a phenethylamine.^1,2 It is biosynthesized by the step-wise double methylation of tyramine (Item No. 18601).³ Hordenine binds to and activates the dopamine D₂ receptor (K_i = 13 µM) but antagonizes D₂ receptor β-arrestin recruitment.⁴ It inhibits tyrosinase activity and expression at concentrations ≥ 50 µM resulting in reduced melanin accumulation in human melanocytes.² Hordenine is present in significant amounts in beer and can be measured in serum in the free form, for up to 2 hours, and the glucuronidated form, for up to 6 hours, after beer consumption.⁵ This product is intended for research and forensic applications.

WARNING This product is not for human or veterinary use.

1. Liu, D.L., and Lovett, J.V. Biologically active secondary metabolites of barley. II. Phytotoxicity of barley allelochemicals. J. Chem. Ecol. 19(10), 2231-2244 (1993).

2. Kim, S.-C., Lee, J.-H., Kim, M.-H., et al. Hordenine, a single compound produced during barley germination, inhibits melanogenesis in human melanocytes. Food Chem. 141(1), 174-181 (2013).

3. Meyer, E. Separation of two distinct S-adenosylmethionine dependent N-methyltransferases involved in hordenine biosynthesis in Hordeum vulgare. Plant Cell Rep. 1(6), 236-239 (1982).

4. Sommer, T., Hübner, H., El Kerdawy, A., et al. Identification of the beer component hordenine as food-derived dopamine D₂ receptor agonist by virtual screening a 3D compound database. Sci. Rep. 7, 44201 (2017).

5. Steiner, I., Brauers, G., Temme, O., et al. A sensitive method for the determination of hordenine in human serum by ESI⁺ UPLC-MS/MS for forensic toxicological applications. Anal. Bioanal. Chem. 408(9), 2285-2292 (2016).