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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. It is biosynthesized by the step-wise double methylation of tyramine (Item No. 18601). Hordenine binds to and activates the dopamine D₂ receptor (K_i = 13 μM) but antagonizes D₂ receptor β-arrestin recruitment. It inhibits tyrosinase activity and expression at concentrations ≥ 50 μM resulting in reduced melanin accumulation in human melanocytes. 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. This product is intended for research and forensic applications.

Light yellow solid

A phenethylamine alkaloid with antibacterial and antibiotic properties found mainly in plants from the cactaceae family. It showed effects similar to Cytosine (C998950) and acted as a depressant on the central nervous system (CNS) during animal testing.

ChEBI: Hordenine is a phenethylamine alkaloid. It has a role as a human metabolite and a mouse metabolite.

Hordenine is an alkaloid found in plants, e.g. the roots of germinating barley and marine algae. It is a metabolite in tyrosine metabolism, biosynthesized from tyramine by two subsequent N-methylations, it is metabolized by monoamine oxidase. Hordenine is a sympathomimetic and its pharmacological actions are of interest, as it is occasionally found in post race urine samples. Hordenine inhibits melanogenesis by suppression of cyclic adenosine monophosphate (cAMP) production. cAMP is involved in the expression of melanogenesis-related proteins. Hordenine may be used in the inhibition of hyperpigmentation. It is present in barley roots from the first day of seed germination, but is not present in seeds.

Crystallise Hordenine from EtOH or H2O and sublime it at 105o/5mm. The 4,4’-dichlorodiphenyl disulfimide salt has m 145-146o (from Me2CO/H2O) [Runge et al. Chem Ber 88 50 1955]. [Beilstein 13 H 626, 13 I 236, 13 II 356, 13 III 1640, 13 IV 1790.]

[1] D L LIU  J V L. Biologically active secondary metabolites of barley. II. Phytotoxicity of barley allelochemicals.[J]. Journal of Chemical Ecology, 1993, 19 10: 2231-2244. DOI: 10.1007/bf00979660
[2] SANG-CHEOL KIM . Hordenine, a single compound produced during barley germination, inhibits melanogenesis in human melanocytes[J]. Food Chemistry, 2013, 141 1: Pages 174-181. DOI: 10.1016/j.foodchem.2013.03.017
[3] MEYER E. Separation of two distinct S-adenosylmethionine dependent N-methyltransferases involved in hordenine biosynthesis in Hordeum vulgare.[J]. Plant Cell Reports, 1982, 1 6: 236-239. DOI: 10.1007/bf00272627
[4] THOMAS SOMMER. Identification of the Beer Component Hordenine as Food-Derived Dopamine D2 Receptor Agonist by Virtual Screening a 3D Compound Database.[J]. ACS Applied Electronic Materials, 2017: 44201. DOI: 10.1038/srep44201
[5] IRINA STEINER. A sensitive method for the determination of hordenine in human serum by ESI+ UPLC-MS/MS for forensic toxicological applications[J]. Analytical and Bioanalytical Chemistry, 2016, 408 9: 2285-2292. DOI: 10.1007/s00216-016-9324-3