HORDENINE

OTHER NAME(S):

Anhaline, Hordenina, Hordénine, N,N-dimethyltyramine, Peyocactin.<br/><br/>

Overview

Overview Information

Hordenine is a chemical naturally found in barley (Hordeum vulgare). 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. It can also be found in algae, cacti, and some grass species.

People take hordenine by mouth for improving athletic performance and weight loss.

How does it work?

Hordenine is similar in chemical structure to stimulants found in bitter orange. Some research shows that it might stimulate the central nervous system, and increase heart rate, blood pressure, and breathing rate. These effects seem to be short-lived and require high doses.

Uses

Uses & Effectiveness?

Insufficient Evidence for

  • Athletic performance.
  • Weight loss.
More evidence is needed to rate hordenine for these uses.

Side Effects

Side Effects & Safety

Hordenine is POSSIBLY UNSAFE when taken by mouth. Hordenine is similar in structure to stimulants found in bitter orange. In theory, hordenine might have similar stimulant effects and side effects such as rapid heart rate and high blood pressure.

Special Precautions & Warnings:

Pregnancy and breast-feeding: There is not enough reliable information about the safety of taking hordenine if you are pregnant or breast feeding. Stay on the safe side and avoid use.

High blood pressure: Hordenine is similar to stimulants found in bitter orange. In theory, taking hordenine might make high blood pressure worse.

Kidney stones: Taking hordenine might increase the risk for kidney stones.

Surgery: Hordenine might interfere with surgery by increasing blood pressure and heart rate. Stop taking hordenine at least 2 weeks before surgery.

Interactions

Interactions?

We currently have no information for HORDENINE Interactions.

Dosing

Dosing

The appropriate dose of hordenine depends on several factors such as the user's age, health, and several other conditions. At this time there is not enough scientific information to determine an appropriate range of doses for hordenine (in children/in adults). Keep in mind that natural products are not always necessarily safe and dosages can be important. Be sure to follow relevant directions on product labels and consult your pharmacist or physician or other healthcare professional before using.

View References

REFERENCES:

  • 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. View abstract.
  • Barwell CJ, Blunden G. Hordenine from the red alga Gigartina stellata. J Nat Prod 1981;44(4):500-2.
  • Batista LM, Almeida RN, da-Cunha EVL, da-Sila MS, Barbosa-Filho JM. Isolation and identification of putative hallucinogenic constituents from the roots of Mimosa ophthalmocentra. Pharm Biol 1999;37(1):50-3.
  • Batista LM, Almeida RN. Central effects of the constituents of Mimosa opthalmocentra Mart. Ex Benth. Acta Farm Bonaerense 1997;16(2):83-6.
  • Berkov S, Pavlov A, Georgiev V, et al. Changes in apolar metabolites during in vitro organogenesis of Pancratium maritimum. Plant Physiol Biochem 2010;48(10-11):827-35. View abstract.
  • 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. View abstract.
  • Bourke CA, Carrigan MJ, Dixon RJ. Experimental evidence that tryptamine alkaloids do not cause Phalaris aquatic sudden death syndrome in sheep. Aust Vet J 1988;65(7):218-20. View abstract,
  • Brady LR, Tyler VE. Biosynthesis of Hordenine in Tissue Homogenates of Panicum miliaceum L. Plant Physiol 1958;33(5):334-8. View abstract.
  • Braga DL, McLaughlin JL. Cactus alkaloids. V. Isolation of hordenine and N-methyltyramine from Ariocarpus retusus. Planta Med 1969;17(1):87-94. View abstract.
  • 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. View abstract.
  • Dietary Ingredient - Hordenine. Dietary Supplement Label Database. National Institutes of Health Web site. Available at: http://www.dsld.nlm.nih.gov/dsld/rptIngredient.jsp?db=adsld&item=HORDENINE. Accessed November 18, 2015.
  • El-Shazly AM, Dora G, Wink M. Alkaloids of Haloxylon salicornicum (Moq.) Bunge ex Boiss. (Chenopodiaceae). Pharmazie 2005;60(12):949-52. View abstract.
  • 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. View abstract.
  • 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. View abstract.
  • Guven KC, Bora A, Sunam G. Hordenine from the alga Phyllophora nervosa. Phytochemistry 1970;9:1893.
  • Hapke HJ, Strathmann W. [Pharmacological effects of hordenine]. Dtsch Tierarztl Wochenschr 1995;102:228-32.. View abstract.
  • Heffter A. Uber Pellote. Ein Beitrag zur pharmakologischen Kenntnis der Cacteen. (Naunyn-Schmiedeberg's). Arch Exp Path Pharm 1894;34:65-86.
  • 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. View abstract.
  • Kawauchi H, Sasaki T. Isolation and identification of hordenine, p-(2-dimethylamino)ethylphenol from Ahnfeltia paradoxa. Bull Jap Soc Sci Fish 1978;44:135-7.
  • Keller WJ. Hordenine from Stapelia gigantea. J Nat Prod 1981;44(3):366-67.
  • 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. View abstract.
  • 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. View abstract.
  • 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.
  • 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. View abstract.
  • Palmer DJ, Sullivan T, Gold MS, Prescott SL, Heddle R, Gibson RA, Makrides M. Randomized controlled trial of fish oil supplementation in pregnancy on childhood allergies. Allergy 2013;68(11):1370-6. View abstract.
  • Percot A, Yalcin A, Erdugan H, Guven KC. Hordenine amount in Phyllophora nervosa (D.C.Grev) (Marine Alga) collected from Sile (the Black Sea) and Dardanelles. Acta Pharm Sci 2007;49:127-32.
  • Pinto Nde C, Duque AP, Pacheco NR, et al. Pereskia aculeate: A plant food with antinociceptive activity. Pharm Biol 2015;53(12):1780-5. View abstract.
  • Ranieri RL, McLaughlin JL. Cactus alkaloids. XXXI. beta-Phenethylamines and tetrahydroisoquinolines from the Mexican cactus dolichothele uberiformis. Lloydia 1977;40(2):173-7. View abstract.
  • Rao GS. Identity of peyocactin, an antibiotic from peyote (Lophophora williamsii), and hordenine. J Pharm Pharmacol 1970;22(7):544-5. View abstract.
  • Shabana M, Gonaid M, Salama MM, Abdel-Sattar E. Phenylalkylamine alkaloids from Stapelia hirsuta L. Nat Prod Res 2006;20(8):710-4. View abstract.
  • 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. View abstract.
  • Unver N, Kaya GI, Werner C, et al. Galanthindole: a new indole alkaloid from Galanthus plicatus ssp. byzantinus. Planta Med 2003;69(9):869-71. View abstract.
  • Wheaton TA, Stewart I. The distribution of tyramine, N-methyltyramine, hordenine, octopamine, and synephrine in higher plants. Lloydia 1970;33(2):244-54. View abstract.
  • Yalcin A, Percot A, Erdugan H, et al. Hordenine in the marine alga, Gelidium crinale (Hare ex Turner) Gaillon. Acta Pharm Sci 2007;49:213-8.
  • 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. View abstract.
  • 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. View abstract.
  • Barwell CJ, Blunden G. Hordenine from the red alga Gigartina stellata. J Nat Prod 1981;44(4):500-2.
  • Batista LM, Almeida RN, da-Cunha EVL, da-Sila MS, Barbosa-Filho JM. Isolation and identification of putative hallucinogenic constituents from the roots of Mimosa ophthalmocentra. Pharm Biol 1999;37(1):50-3.
  • Batista LM, Almeida RN. Central effects of the constituents of Mimosa opthalmocentra Mart. Ex Benth. Acta Farm Bonaerense 1997;16(2):83-6.
  • Berkov S, Pavlov A, Georgiev V, et al. Changes in apolar metabolites during in vitro organogenesis of Pancratium maritimum. Plant Physiol Biochem 2010;48(10-11):827-35. View abstract.
  • 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. View abstract.
  • Bourke CA, Carrigan MJ, Dixon RJ. Experimental evidence that tryptamine alkaloids do not cause Phalaris aquatic sudden death syndrome in sheep. Aust Vet J 1988;65(7):218-20. View abstract,
  • Brady LR, Tyler VE. Biosynthesis of Hordenine in Tissue Homogenates of Panicum miliaceum L. Plant Physiol 1958;33(5):334-8. View abstract.
  • Braga DL, McLaughlin JL. Cactus alkaloids. V. Isolation of hordenine and N-methyltyramine from Ariocarpus retusus. Planta Med 1969;17(1):87-94. View abstract.
  • 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. View abstract.
  • Dietary Ingredient - Hordenine. Dietary Supplement Label Database. National Institutes of Health Web site. Available at: http://www.dsld.nlm.nih.gov/dsld/rptIngredient.jsp?db=adsld&item=HORDENINE. Accessed November 18, 2015.
  • El-Shazly AM, Dora G, Wink M. Alkaloids of Haloxylon salicornicum (Moq.) Bunge ex Boiss. (Chenopodiaceae). Pharmazie 2005;60(12):949-52. View abstract.
  • 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. View abstract.
  • Fritz H, Kennedy D, Fergusson D, et al. Selenium and lung cancer: A systematic review and meta-analysis. PLoS One 2011;6(11):e26259. View abstract.
  • 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. View abstract.
  • Guven KC, Bora A, Sunam G. Hordenine from the alga Phyllophora nervosa. Phytochemistry 1970;9:1893.
  • Hapke HJ, Strathmann W. [Pharmacological effects of hordenine]. Dtsch Tierarztl Wochenschr 1995;102:228-32.. View abstract.
  • Heffter A. Uber Pellote. Ein Beitrag zur pharmakologischen Kenntnis der Cacteen. (Naunyn-Schmiedeberg's). Arch Exp Path Pharm 1894;34:65-86.
  • 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. View abstract.
  • Kawauchi H, Sasaki T. Isolation and identification of hordenine, p-(2-dimethylamino)ethylphenol from Ahnfeltia paradoxa. Bull Jap Soc Sci Fish 1978;44:135-7.
  • Keller WJ. Hordenine from Stapelia gigantea. J Nat Prod 1981;44(3):366-67.
  • 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. View abstract.
  • 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. View abstract.
  • 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. View abstract.
  • 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.
  • 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. View abstract.
  • Palmer DJ, Sullivan T, Gold MS, Prescott SL, Heddle R, Gibson RA, Makrides M. Randomized controlled trial of fish oil supplementation in pregnancy on childhood allergies. Allergy 2013;68(11):1370-6. View abstract.
  • Percot A, Yalcin A, Erdugan H, Guven KC. Hordenine amount in Phyllophora nervosa (D.C.Grev) (Marine Alga) collected from Sile (the Black Sea) and Dardanelles. Acta Pharm Sci 2007;49:127-32.
  • Pinto Nde C, Duque AP, Pacheco NR, et al. Pereskia aculeate: A plant food with antinociceptive activity. Pharm Biol 2015;53(12):1780-5. View abstract.
  • Ranieri RL, McLaughlin JL. Cactus alkaloids. XXXI. beta-Phenethylamines and tetrahydroisoquinolines from the Mexican cactus dolichothele uberiformis. Lloydia 1977;40(2):173-7. View abstract.
  • Rao GS. Identity of peyocactin, an antibiotic from peyote (Lophophora williamsii), and hordenine. J Pharm Pharmacol 1970;22(7):544-5. View abstract.
  • Shabana M, Gonaid M, Salama MM, Abdel-Sattar E. Phenylalkylamine alkaloids from Stapelia hirsuta L. Nat Prod Res 2006;20(8):710-4. View abstract.
  • 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. View abstract.
  • Unver N, Kaya GI, Werner C, et al. Galanthindole: a new indole alkaloid from Galanthus plicatus ssp. byzantinus. Planta Med 2003;69(9):869-71. View abstract.
  • Wheaton TA, Stewart I. The distribution of tyramine, N-methyltyramine, hordenine, octopamine, and synephrine in higher plants. Lloydia 1970;33(2):244-54. View abstract.
  • Yalcin A, Percot A, Erdugan H, et al. Hordenine in the marine alga, Gelidium crinale (Hare ex Turner) Gaillon. Acta Pharm Sci 2007;49:213-8.
  • 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. View abstract.

More Resources for HORDENINE

CONDITIONS OF USE AND IMPORTANT INFORMATION: This information is meant to supplement, not replace advice from your doctor or healthcare provider and is not meant to cover all possible uses, precautions, interactions or adverse effects. This information may not fit your specific health circumstances. Never delay or disregard seeking professional medical advice from your doctor or other qualified health care provider because of something you have read on WebMD. You should always speak with your doctor or health care professional before you start, stop, or change any prescribed part of your health care plan or treatment and to determine what course of therapy is right for you.

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