Hordenine

Last Updated: September 28 2022

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.

Hordenine is most often used for




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    1.

    Sources and Structure

    1.1

    Sources and Structure

    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.

    2.

    Pharmacology

    2.1

    Metabolism

    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]

    2.2

    Drug Testing

    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]

    3.

    Neurology

    3.1

    Adrenaline

    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 WPharmacological effects of hordenineDtsch Tierarztl Wochenschr.(1995 Jun)
    2.^Frank M, Weckman TJ, Wood T, Woods WE, Tai CL, Chang SL, Ewing A, Blake JW, Tobin THordenine: pharmacology, pharmacokinetics and behavioural effects in the horseEquine Vet J.(1990 Nov)
    3.^Sander LC, Putzbach K, Nelson BC, Rimmer CA, Bedner M, Thomas JB, Porter BJ, Wood LJ, Schantz MM, Murphy KE, Sharpless KE, Wise SA, Yen JH, Siitonen PH, Evans RL, Nguyen Pho A, Roman MC, Betz JMCertification of standard reference materials containing bitter orangeAnal Bioanal Chem.(2008 Jul)
    4.^Nelson BC, Putzbach K, Sharpless KE, Sander LCMass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium)J Agric Food Chem.(2007 Nov 28)
    7.^Wainwright T, Slack PT, Long DEN-nitrosodimethylamine precursors in maltIARC Sci Publ.(1982)
    8.^Berkov S, Bastida J, Sidjimova B, Viladomat F, Codina CAlkaloid diversity in Galanthus elwesii and Galanthus nivalisChem Biodivers.(2011 Jan)
    9.^Berkov S, Reyes-Chilpa R, Codina C, Viladomat F, Bastida JRevised NMR data for incartine: an alkaloid from Galanthus elwesiiMolecules.(2007 Jul 12)
    12.^Tan D, Chen Y, Ji L, Chou G, Wang ZAlkaloids from Senecio scandensZhongguo Zhong Yao Za Zhi.(2010 Oct)
    13.^Berkov S, Pavlov A, Georgiev V, Weber J, Bley T, Viladomat F, Bastida J, Codina CChanges in apolar metabolites during in vitro organogenesis of Pancratium maritimumPlant Physiol Biochem.(2010 Oct-Nov)
    14.^Sashidhara KV, Singh SP, Shukla PKAntimicrobial evaluation of clerodane diterpenes from Polyalthia longifolia var. pendulaNat Prod Commun.(2009 Mar)
    15.^Barwell CJ, Basma AN, Lafi MA, Leake LDDeamination of hordenine by monoamine oxidase and its action on vasa deferentia of the ratJ Pharm Pharmacol.(1989 Jun)