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meta-Tyramine, also known as m-tyramine and 3-tyramine, as well as 3-hydroxyphenethylamine, is an endogenous trace amine neuromodulator and a structural analog of phenethylamine.[1][2][3] It is a positional isomer of para-tyramine, and similarly to it, has effects on the adrenergic and dopaminergic systems.[4][5]

meta-Tyramine is produced in humans via aromatic amino acid decarboxylase-mediated metabolism of meta-tyrosine.[6] meta-Tyramine can be metabolized into dopamine via peripheral or brain CYP2D6 enzymes in humans.[7]

See also

References

  1. ^ Boulton AA, Huebert ND (November 1981). “Biosynthesis of some urinary trace amines in the rat and the human”. Research Communications in Chemical Pathology and Pharmacology. 34 (2): 295–310. PMID 7335956.
  2. ^ Dyck LE, Juorio AV, Boulton AA (June 1982). “The in vitro release of endogenous m-tyramine, p-tyramine and dopamine from rat striatum”. Neurochemical Research. 7 (6): 705–16. doi:10.1007/bf00965523. PMID 7121718. S2CID 20758261.
  3. ^ Sardar A, Juorio AV, Boulton AA (June 1987). “The concentration of p- and m-tyramine in the rat mesolimbic system: its regional distribution and effect of monoamine oxidase inhibition”. Brain Research. 412 (2): 370–4. doi:10.1016/0006-8993(87)91145-0. PMID 3607473. S2CID 34094088.
  4. ^ Dyck LE, Kazakoff CW, Dourish CT (October 1982). “The role of catecholamines, 5-hydroxytryptamine and m-tyramine in the behavioural effects of m-tyrosine in the rat”. European Journal of Pharmacology. 84 (3–4): 139–49. doi:10.1016/0014-2999(82)90196-0. PMID 7173317.
  5. ^ McQuade PS, Wood PL (1984). “The effects of administration of meta-tyramine and para-tyramine on dopamine and its metabolites in the rat striatum”. Progress in Neuro-psychopharmacology & Biological Psychiatry. 8 (4–6): 705–9. doi:10.1016/0278-5846(84)90042-3. PMID 6531442. S2CID 24889205.
  6. ^ EC 4.1.1.28 – Aromatic-L-amino-acid decarboxylase (Homo sapiens). Technische Universität Braunschweig. July 2016. Retrieved 7 October 2016. Substrate: m-tyrosine

    Product: m-tyramine + CO2

    Organism: Homo sapiens     {{cite encyclopedia}}: |website= ignored (help)
    Reaction diagram
  7. ^ Wang X, Li J, Dong G, Yue J (February 2014). “The endogenous substrates of brain CYP2D”. Eur. J. Pharmacol. 724: 211–218. doi:10.1016/j.ejphar.2013.12.025. PMID 24374199. The highest level of brain CYP2D activity was found in the substantia nigra … The in vitro and in vivo studies have shown the contribution of the alternative CYP2D-mediated dopamine synthesis to the concentration of this neurotransmitter although the classic biosynthetic route to dopamine from tyrosine is active. … Tyramine levels are especially high in the basal ganglia and limbic system, which are thought to be related to individual behavior and emotion (Yu et al., 2003c). … Rat CYP2D isoforms (2D2/2D4/2D18) are less efficient than human CYP2D6 for the generation of dopamine from p-tyramine. The Km values of the CYP2D isoforms are as follows: CYP2D6 (87–121 μm) ≈ CYP2D2 ≈ CYP2D18 > CYP2D4 (256 μm) for m-tyramine and CYP2D4 (433 μm) > CYP2D2 ≈ CYP2D6 > CYP2D18 (688 μm) for p-tyramine