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Chemical Compound Review

Metatyramine     3-(2-aminoethyl)phenol

Synonyms: m-Tyramine, meta-Tyramine, SureCN43719, CHEMBL145584, AG-C-56125, ...
 
 
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Disease relevance of m-Tyramine

  • This apparent anomaly is attributed to smaller metabolic compartments in phenylketonuria and a lower threshold for the metabolism of m-tyramine via beta-hydroxylation [1].
 

High impact information on m-Tyramine

  • The uphill uptake of external DA, the lack of inhibition by internal substrates on DA uptake, and the accelerated exchange of internal DA by external m-tyramine support a carrier model in which the hNET alternates between outward-facing and inward-facing conformations [2].
  • Regional analysis of the trace amines phenylethylamine, p-tyramine, m-tyramine, and tryptamine has indicated that the amines are distributed heterogeneously throughout the brain, but are most concentrated in the basal ganglia [3].
  • S(+)-Amphetamine and m-tyramine inhibited sDAT activity for dopamine by competing for a common binding site with dopamine and each other, suggesting that phenethylamines are substrate analogues at the plasmalemmal sDAT [4].
  • The title compounds were designed to provide semirigid congeners of m-tyramine in which the ring position ortho to the phenolic OH is blocked to metabolic hydroxylation [5].
  • Significant reductions in the striatal concentrations of m-tyramine 2 h after the administration of AMPT, suggest that tyrosine hydroxylase is involved similarly in the production of m-tyramine [6].
 

Anatomical context of m-Tyramine

  • The behavioural syndrome induced consisted of forepaw padding, headweaving, backward walking, splayed hindlimbs, wet dog shakes, hyperactivity and hyperreactivity. m-Tyrosine alone or in combination with pargyline caused a significant increase in brain m-tyramine levels and a significant depletion of catecholamines [7].
  • Nutritional stress induced in pre-weaning (3 weeks of age) or post-weaning (up to 9 weeks of age) rats resulted in a decrease in the concentration of p-tyramine and an increase in the concentration of m-tyramine in the caudate nucleus [8].
  • Administration of chlordimeform (50 mg/Kg, i.p.) resulted in an increase in p- and m-tyramine concentrations in the striatum but not that of p-octopamine in the hypothalamus [9].
  • The p- and m-tyramine concentrations were not reduced at 7 days after the raphé nuclei lesions indicating that if the striatal tyramine-containing neurons exist, they do not originate in or pass through the dorsal or median raphé nuclei [10].
  • These experiments show that in the rat corpus striatum the highest concentrations of p- and m-tyramine were found in the caudate nucleus while somewhat lower values were observed in the putamen and globus pallidus [11].
 

Associations of m-Tyramine with other chemical compounds

 

Gene context of m-Tyramine

 

Analytical, diagnostic and therapeutic context of m-Tyramine

References

  1. The metabolism of L-m-tyrosine: the use of a putative precursor to investigate the increased production of m-hydroxymandelic acid in phenylketonuria. Hoskins, J.A., Greenway, A.M. Clin. Chim. Acta (1983) [Pubmed]
  2. Cocaine acts as an apparent competitive inhibitor at the outward-facing conformation of the human norepinephrine transporter: kinetic analysis of inward and outward transport. Chen, N., Justice, J.B. J. Neurosci. (1998) [Pubmed]
  3. Evidence for the presence of m-tyramine, p-tyramine, tryptamine, and phenylethylamine in the rat brain and several areas of the human brain. Philips, S.R., Rozdilsky, B., Boulton, A.A. Biol. Psychiatry (1978) [Pubmed]
  4. Relationships between the catechol substrate binding site and amphetamine, cocaine, and mazindol binding sites in a kinetic model of the striatal transporter of dopamine in vitro. Wayment, H., Meiergerd, S.M., Schenk, J.O. J. Neurochem. (1998) [Pubmed]
  5. Derivatives of 5-hydroxy-6-methyl-2-aminotetralin. Cannon, J.G., Koble, D.L., Long, J.P., Verimer, T. J. Med. Chem. (1980) [Pubmed]
  6. The effects of (+)-amphetamine, alpha-methyltyrosine, and alpha-methylphenylalanine on the concentrations of m-tyramine and alpha-methyl-m-tyramine in rat striatum. Dougan, D.F., Duffield, A.M., Duffield, P.H., Wade, D.N. Br. J. Pharmacol. (1983) [Pubmed]
  7. The role of catecholamines, 5-hydroxytryptamine and m-tyramine in the behavioural effects of m-tyrosine in the rat. Dyck, L.E., Kazakoff, C.W., Dourish, C.T. Eur. J. Pharmacol. (1982) [Pubmed]
  8. Effects of nutritional stress on brain tyramine concentration and dopamine turnover. Bhave, S.V., Telang, S.D., Durden, D.A., Juorio, A.V. Neurochem. Res. (1988) [Pubmed]
  9. Effect of chlordimeform and clonidine on the turnover of P-octopamine in rat hypothalamus and striatum. Duffield, P.H., Dougan, D.F., Wade, D.N., Duffield, A.M. Life Sci. (1986) [Pubmed]
  10. The effect of raphé nuclei lesions on striatal tyramine concentration and dopamine turnover in the rat. Juorio, A.V., Greenshaw, A.J. Neurochem. Res. (1986) [Pubmed]
  11. The regional distribution of p-tyramine and m-tyramine in the rat corpus striatum and the effect of monoamine oxidase inhibition. Sardar, A., Juorio, A.V. Prog. Neuropsychopharmacol. Biol. Psychiatry (1987) [Pubmed]
  12. The effect of some decarboxylase inhibitors on striatal tyramines in the mouse. Juorio, A.V. Neuropharmacology (1983) [Pubmed]
  13. Presence and metabolism of beta-phenylethylamine, p-tyramine, m-tyramine and tryptamine in the brain of the domestic fowl. Juorio, A.V. Brain Res. (1976) [Pubmed]
  14. Evidence that pure uptake inhibitors including cocaine interact slowly with the dopamine neuronal carrier. Héron, C., Costentin, J., Bonnet, J.J. Eur. J. Pharmacol. (1994) [Pubmed]
  15. Dopamine formation from tyramine by CYP2D6. Hiroi, T., Imaoka, S., Funae, Y. Biochem. Biophys. Res. Commun. (1998) [Pubmed]
  16. Identification and distribution of m-tyramine in the rat. Philips, S.R., Davis, B.A., Durden, D.A., Boulton, A.A. Can. J. Biochem. (1975) [Pubmed]
 
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