Hordenine

OTHER NAME(S): 4-[2-(Dimethylamino)Ethyl]Phenol, 4-hydroxy-N,N-dimethylphenethylamine, Anhaline, Eremursine, P-Hydroxy-N,N-Dimethylphenethylamine, Peyocactin, Peyocactine, N,N-dimethyltyramine, Hordenine HCl, Hordenina, Hordénine

Overview

Hordenine is a chemical naturally found in barley (Hordeum vulgare). It can also be found in algae, cacti, and some grass species. It is similar in chemical structure to stimulants found in bitter orange. Hordenine is included in many dietary supplements used for athletic performance and weight loss.

People take hordenine by mouth for obesity and improving athletic performance, but there is no good scientific evidence to support these uses.

References
  1. Singh AK, Granley K, Misrha U, et al. Screening and confirmation of drugs in urine: interference of hordenine with the immunoassays and thin layer chromatography methods. Forensic Sci Int 1992;54:9-22.
  2. Hapke HJ, Strathmann W. [Pharmacological effects of hordenine]. Dtsch Tierarztl Wochenschr 1995;102:228-32..
  3. Mann JD, Steinhart CE, Mudd SH. Alkaloids and plant metabolism: V. The distribution and formation of tyramine methylpherase during germination of barley. J Biol Chem 1963;238:676-81.
  4. Barwell CJ, Blunden G. Hordenine from the red alga Gigartina stellata. J Nat Prod 1981;44(4):500-2.
  5. Barwell CJ, Basma AN, Lafi MA, Leake LD. Deamination of hordenine by monoamine oxidase and its action on vasa deferentia of the rat. J Pharm Pharmacol 1989;41(6):421-3.
  6. Frank M, Weckman TJ, Wood T, et al. Hordenine: pharmacology, pharmacokinetics and behavioural effects in the horse. Equine Vet J 1990;22(6):437-41.
  7. Lovett JV, Hoult AH, Christen O. Biologically active secondary metabolites of barley. IV. Hordenine production by different barley lines. J Chem Ecol 1994;20(8):1945-54.
  8. Yokoo Y, Kohda H, Kusumoto A, et al. Isolation from beer and structural determination of a potent stimulant of gastrin release. Alcohol Alcohol 1999;34(2):161-8.
  9. Nelson BC, Putzbach K, Sharpless KE, Sander LC. Mass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium). J Agric Food Chem 2007;55(24):9769-75.
  10. Beury-Cirou A, Tannieres M, Minard C, et al. At a supra-physiological concentration, human sexual hormones act as quorum-sensing inhibitors. PLoS One 2013;8(12):e83564.
  11. Kim SC, Lee JH, Kim MH, et al. Hordenine, a single compound produced during barley germination, inhibits melanogenesis in human melanocytes. Food Chem 2013;141(1):174-81.
  12. Heffter A. Uber Pellote. Ein Beitrag zur pharmakologischen Kenntnis der Cacteen. (Naunyn-Schmiedeberg's). Arch Exp Path Pharm 1894;34:65-86.
  13. Hoult AH, Lovett JV. Biologically active secondary metabolites of barley. III. A method for identification and quantification of hordenine and gramine in barley by high-performance liquid chromatography. J Chem Ecol 1993;19(10):2245-54.
  14. Goelz MF, Rothenbacher H, Wiggins JP, et al. Some hematological and histopathological effects of the alkaloids gramine and hordenine on meadow voles (Microtus pennsylvanicus). Toxicology 1980;18(2):125-31.
  15. Dietary Ingredient - Hordenine. Dietary Supplement Label Database. National Institutes of Health Web site. Available at: https://www.dsld.nlm.nih.gov/dsld/rptIngredient.jsp?db=adsld&item=HORDENINE. Accessed November 18, 2015.
  16. Daly JW, Creveling CR, Witkop B. The chemorelease of norepinephrine from mouse hearts. Structure-activity relationships. I. Sympathomimetic and related amines. J Med Chem 1966;9(3):273-80.
  17. Liu Y, Santillo MF. Cytochrome P450 2D6 and 3A4 enzyme inhibition by amine stimulants in dietary supplements. Drug Test Anal. 2016;8(3-4):307-10.
  18. Gonzalez Viejo C, Villarreal-Lara R, Torrico DD, et al. Beer and consumer response using biometrics: associations assessment of beer compounds and elicited emotions. Foods. 2020;9(6):E821.
  19. Sommer T, Göen T, Budnik N, Pischetsrieder M. Absorption, biokinetics, and metabolism of the dopamine D2 receptor agonist hordenine (N,N-dimethyltyramine) after beer consumption in humans. J Agric Food Chem. 2020;68(7):1998-2006.
  20. Sobiech M, Giebultowicz J, Lulinski P. Application of magnetic core-shell imprinted nanoconjugates for the analysis of hordenine in human plasma - preliminary data on pharmacokinetic study after oral administration. J Agric Food Chem. 2020 Dec 9;68(49):14502-12.