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Hordenine

Hordenine (N,N-dimethyltyramine) is an adrenergic-like compound found in a variety of foods investigated for its fat-burning effects. May be a noradrenaline reuptake inhibitor.

Our evidence-based analysis on hordenine features 18 unique references to scientific papers.

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Summary of Hordenine

Primary Information, Benefits, Effects, and Important Facts

Hordenine is a molecule found in a variety of plants alongside other adrenergic amines such as tyramine or synephrine, and has been linked to having adrenergic effects after intravenous administration. Practically, Hordenine is very underresearched and comparative analysis' between other stimulants cannot be conducted right now.

Technically Hordenine can be used as a stimulant and fat burner due to its associated with tyramine and noradrenaline, but not enough evidence exists currently to support its usage as nutritional supplementation.

Hordenine is on the FDA's Dietary Supplement Ingredient Advisory List as of April, 2019. These are ingredients that do not appear to be lawful ingredients in dietary supplements. The list is subject to change (check the provided link for current status).

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Things To Know & Note

Is a Form Of

Primary Function:

Also Known As

N, N-dimethyltyramine

Do Not Confuse With

Tyramine, Candicine, L-Tyrosine

  • Most likely stimulatory following high dose oral consumption

How to Take Hordenine

Recommended dosage, active amounts, other details

There is currently insufficient evidence to recommend an oral dose of hordenine supplementation for human consumption.

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Scientific Research on Hordenine

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Hordenine (N,N-dimethyltyramine) is a protoalkaloid related to tyramine (known as 4-hydroxyphenethylamine and derived from L-Tyrosine) that came to light after it appeared in the serum or horses fed sprouted barley (containing Hordenine) and indirectly acted as an adrenergic drug,[1] although the doses found in their feed did not mimick the clear stimulant effects following injections.[2] Other related structures include N-methyltyramine (a lone methyl group on the nitrogen atom) and Candicine, with three methyl groups on the nitrogen atom.

Hordenine can be found as a component of:

  • Bitter Orange[3][4][5]

  • Barley, sprouted barley, and malt[6][7]

  • The Galanthus genera of plants[8][9]

  • The Ariocarpus (Cactus) genera of plants[10][11]

  • Senecio scandens[12]

  • Pancratium maritimum[13]

  • Polyalthia longifolia[14]

Hordenine is one of the many biogenic amines in bitter orange that have since become dietary supplements, including synephrine and octopamine.

Hordenine is subject to metabolism (deamination) via Monoamine Oxidase subset B (MAOB) with minimal metabolism by the MAO-A subset.[15] This selective metabolism by MAO-B rather than MAO-A lessens the possible risk that is seem with the related structure Tyramine and Monoamine Oxidase inhibitors (known as the cheese effect, which leads to hypertensive crisises) which is more MAO-A dependent.[16]

Hordenine has been found to interact with Morphine testing drug kits, which extended to oxymorphone, hydromorphone and apomorphine with less reactivity to tests for etorphine- and buprenorphine; the authors suggested that high dose Hordenine can cause a false positive for Morphine and related structures.[17]

One study in isolated rat vas deferas muscles noted that Hordenine was able to augment adrenaline-induced contractions without inherently inducing contractions, suggesting it worked via acting as a noradrenaline reuptake inhibitor.[15][18] This may be related to the clear adrenaline-like effects found after injections of 2mg/kg into horses (to reach serum levels of 1mcg/mL) which include a doubling of heart rate and induction of respiratory rate.[2]

References

  1. ^ Hapke HJ, Strathmann W. Pharmacological effects of hordenine. Dtsch Tierarztl Wochenschr. (1995)
  2. ^ a b Frank M, et al. Hordenine: pharmacology, pharmacokinetics and behavioural effects in the horse. Equine Vet J. (1990)
  3. ^ Sander LC, et al. Certification of standard reference materials containing bitter orange. Anal Bioanal Chem. (2008)
  4. ^ Nelson BC, et al. Mass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium). J Agric Food Chem. (2007)
  5. ^ Pellati F, Benvenuti S. Chromatographic and electrophoretic methods for the analysis of phenethylamine {corrected} alkaloids in Citrus aurantium. J Chromatogr A. (2007)
  6. ^ Mangino MM, Scanlan RA. Rapid formation of N-nitrosodimethylamine from gramine, a naturally occurring precursor in barley malt. IARC Sci Publ. (1984)
  7. ^ Wainwright T, Slack PT, Long DE. N-nitrosodimethylamine precursors in malt. IARC Sci Publ. (1982)
  8. ^ Berkov S, et al. Alkaloid diversity in Galanthus elwesii and Galanthus nivalis. Chem Biodivers. (2011)
  9. ^ Berkov S, et al. Revised NMR data for incartine: an alkaloid from Galanthus elwesii. Molecules. (2007)
  10. ^ Wheaton TA, Stewart I. The distribution of tyramine, N-methyltyramine, hordenine, octopamine, and synephrine in higher plants. Lloydia. (1970)
  11. ^ McLaughlin JL. Cactus alkaloids. VI. Identification of hordenine and N--methyltyramine in Ariocarpus fissuratus varieties fissuratus and lloydii. Lloydia. (1969)
  12. ^ Tan D, et al. Alkaloids from Senecio scandens. Zhongguo Zhong Yao Za Zhi. (2010)
  13. ^ Berkov S, et al. Changes in apolar metabolites during in vitro organogenesis of Pancratium maritimum. Plant Physiol Biochem. (2010)
  14. ^ Sashidhara KV, Singh SP, Shukla PK. Antimicrobial evaluation of clerodane diterpenes from Polyalthia longifolia var. pendula. Nat Prod Commun. (2009)
  15. ^ a b Barwell CJ, et al. Deamination of hordenine by monoamine oxidase and its action on vasa deferentia of the rat. J Pharm Pharmacol. (1989)
  16. ^ Finberg JP, Gillman K. Selective inhibitors of monoamine oxidase type B and the "cheese effect". Int Rev Neurobiol. (2011)
  17. ^ Singh AK, et al. Screening and confirmation of drugs in urine: interference of hordenine with the immunoassays and thin layer chromatography methods. Forensic Sci Int. (1992)
  18. ^ Nedergaard OA, Westermann E. Action of various sympathomimetic amines on the isolated stripped vas deferens of the guinea-pig. Br J Pharmacol. (1968)