o-Phenyl-3-iodotyramine

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o-Phenyl-3-iodotyramine
O-Phenyl-3-iodotyramine structure.png
Systematic (IUPAC) name
2-(3-Iodo-4-phenoxyphenyl)ethanamine
Identifiers
PubChem CID: 11501691
ChemSpider 9676493
Chemical data
Formula C14H14INO
Molecular mass 339.171 g/mol
  • Ic1cc(CCN)ccc1Oc2ccccc2
  • InChI=1S/C14H14INO/c15-13-10-11(8-9-16)6-7-14(13)17-12-4-2-1-3-5-12/h1-7,10H,8-9,16H2

o-Phenyl-3-iodotyramine (o-PIT) is a drug which acts as a selective agonist for the trace amine-associated receptor 1. It has reasonable selectivity for TAAR1 but relatively low potency, and is rapidly metabolised in vivo, making it less useful for research than newer ligands such as RO5166017.[1][2][3][4]

References

  1. ↑ Zucchi R, Chiellini G, Scanlan TS, Grandy DK. Trace amine-associated receptors and their ligands. British Journal of Pharmacology. 2006 Dec;149(8):967-78. PMID 17088868
  2. ↑ Ledonne A, Federici M, Giustizieri M, Pessia M, Imbrici P, Millan MJ, Bernardi G, Mercuri NB. Trace amines depress D(2)-autoreceptor-mediated responses on midbrain dopaminergic cells. British Journal of Pharmacology. 2010 Jul;160(6):1509-20. PMID 20590640
  3. ↑ Revel FG, Moreau JL, Gainetdinov RR, Bradaia A, Sotnikova TD, Mory R, Durkin S, Zbinden KG, Norcross R, Meyer CA, Metzler V, Chaboz S, Ozmen L, Trube G, Pouzet B, Bettler B, Caron MG, Wettstein JG, Hoener MC. TAAR1 activation modulates monoaminergic neurotransmission, preventing hyperdopaminergic and hypoglutamatergic activity. Proceedings of the National Academy of Sciences USA. 2011 May 17;108(20):8485-90. PMID 21525407
  4. ↑ Di Cara B, Maggio R, Aloisi G, Rivet JM, Lundius EG, Yoshitake T, Svenningsson P, Brocco M, Gobert A, De Groote L, Cistarelli L, Veiga S, De Montrion C, Rodriguez M, Galizzi JP, Lockhart BP, Cogé F, Boutin JA, Vayer P, Verdouw PM, Groenink L, Millan MJ. Genetic deletion of trace amine 1 receptors reveals their role in auto-inhibiting the actions of ecstasy (MDMA). Journal of Neuroscience. 2011 Nov 23;31(47):16928-40. PMID 22114263


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