Chemistry:Meta-Tyramine
From HandWiki
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| Names | |
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| Preferred IUPAC name
3-(2-Aminoethyl)phenol | |
| Other names
m-Tyramine; 3-Tyramine;
3-Hydroxyphenylethylamine | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C8H11NO | |
| Molar mass | 137.182 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
meta-Tyramine, also known as m-tyramine and 3-tyramine, 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
- ↑ "Biosynthesis of some urinary trace amines in the rat and the human". Research Communications in Chemical Pathology and Pharmacology 34 (2): 295–310. November 1981. PMID 7335956.
- ↑ "The in vitro release of endogenous m-tyramine, p-tyramine and dopamine from rat striatum". Neurochemical Research 7 (6): 705–16. June 1982. doi:10.1007/bf00965523. PMID 7121718.
- ↑ "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. June 1987. doi:10.1016/0006-8993(87)91145-0. PMID 3607473.
- ↑ "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. October 1982. doi:10.1016/0014-2999(82)90196-0. PMID 7173317.
- ↑ "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. 1984. doi:10.1016/0278-5846(84)90042-3. PMID 6531442.
- ↑ "EC 4.1.1.28 – Aromatic-L-amino-acid decarboxylase (Homo sapiens)". EC 4.1.1.28 – Aromatic-L-amino-acid decarboxylase (Homo sapiens). Technische Universität Braunschweig. July 2016. http://www.brenda-enzymes.org/enzyme.php?ecno=4.1.1.28&Suchword=&reference=&organism%5B%5D=Homo+sapiens&show_tm=0. Retrieved 7 October 2016. "Substrate: m-tyrosine
Product: m-tyramine + CO2
Organism: Homo sapiens".
Reaction diagram - ↑ "The endogenous substrates of brain CYP2D". Eur. J. Pharmacol. 724: 211–218. February 2014. 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".
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