Tiramin
Tiramin (4-hidroksifenetilamin, para-tiramin, midrijal, uteramin) je prirodni monoamin jedinjenje i trag amin izveden iz aminokiseline tirozina.[6] Tiramin deluje kao kateholamin [ dopamin, norepinefrin (noradrenalin), epinefrin (adrenalin)] otpuštajući agenst. On nema sposobnost prolaska kroz krvno moždanu barijeru, te ispoljava jedino periferne simpatomimetičke efekte.
| Tiramin | |||
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| IUPAC ime |
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| Identifikacija | |||
| CAS registarski broj | 51-67-2 
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| PubChem[1][2] | 5610 | ||
| ChemSpider[3] | 5408
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| UNII | X8ZC7V0OX3
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| KEGG[4] | |||
| MeSH | |||
| ChEBI | 15760 | ||
| ChEMBL[5] | CHEMBL11608
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| Jmol-3D slike | Slika 1 | ||
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| Svojstva | |||
| Molekulska formula | C8H11NO | ||
| Molarna masa | 137,179 g/mol[6] | ||
| Agregatno stanje | Bezbojna tečnost | ||
| Gustina | 1,20 g/cm3[7] | ||
| Tačka topljenja |
164-165 °C [8] | ||
| Tačka ključanja |
205-207 °C na 25 mm Hg; 166 °C na 2 mm Hg [8] | ||
| Rastvorljivost u vodi | 1 g in 95 mL na 15 °C [8] | ||
| pKa | 9,74 (OH); 10,52 (NH3+) [9] | ||
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Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala | |||
| Infobox references | |||
Biosinteza
urediBiohemijski, tiramin se formira dekarboksilacijom tirozina posredstvom enzima tirozin dekarboksilaza.[10] Tiramin se zatim može konvertovati do metilisanih alkaloidnih derivata N-metiltiramina, N,N-dimetiltiramina (hordenina), o N,N,N-trimetiltiramina (kandicina).
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Tiramin -
N-Metiltiramin -
N,N-Dimetiltiramin (hordenin) -
N,N,N-Trimetiltiramin (kandicin)
Hemija
urediU laboratoriji, tiramin se može sintetisati na različite načine, uključujući dekarboksilaciju tirozina.[11][12][13]
Reference
uredi- ↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519.
- ↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
- ↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846.
- ↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
- ↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594.
- ↑ 6,0 6,1 PubChem
- ↑ A. M. Andersen (1977). "The crystal and molecular structure of tyramine hydrochloride." Acta Chem. Scandinavica B 31 162-166.
- ↑ 8,0 8,1 8,2 The Merck Index, 10th Ed. (1983), p.1405, Rahway: Merck & Co.
- ↑ Kappe, T. (1965). „Ultraviolet Absorption Spectra and Apparent Acidic Dissociation Constants of Some Phenolic Amines”. Journal of Medicinal Chemistry 8: 368-374.
- ↑ Tyrosine metabolism - Reference pathway Arhivirano 2019-07-26 na Wayback Machine-u, Kyoto Encyclopedia of Genes and Genomes (KEGG)
- ↑ G. Barger (1909). „CXXVII.—Isolation and synthesis of p-hydroxyphenylethylamine, an active principle of ergot soluble in water”. J. Chem. Soc. 95: 1123.
- ↑ Waser, Ernst (1925). „Untersuchungen in der Phenylalanin-Reihe VI. Decarboxylierung des Tyrosins und des Leucins”. Helvetica Chimica Acta 8: 758. DOI:10.1002/hlca.192500801106.
- ↑ Buck, Johannes S. (1933). „Reduction of Hydroxymandelonitriles. A New Synthesis of Tyramine”. Journal of the American Chemical Society 55 (8): 3388. DOI:10.1021/ja01335a058.
