O-Phenyl-3-iodotyramine

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O-Phenyl-3-iodotyramine

Systematic (IUPAC) name
2-(3-Iodo-4-phenoxyphenyl)ethanamine
Clinical data
Legal status	?
Identifiers

ATC code	?
PubChem	CID 11501691
Chemical data
Formula	C₁₄H₁₄I N O
Mol. mass	339.171 g/mol
SMILES Ic1cc(CCN)ccc1Oc2ccccc2

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

↑ 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
↑ 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
↑ 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
↑ 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

Trace amine-associated receptor (TAAR) ligands

TAAR1

Agonists

Selective:	O-Phenyl-3-iodotyramine RO5166017

Non-selective:	3-Iodothyronamine 3-Methoxytyramine 5-MeO-DMT Amphetamine Bromocriptine DMT DOI Dopamine LSD m-Octopamine m-Tyramine MDMA Methamphetamine N-Methylphenethylamine N-Methyltryptamine N-Methyltyramine Norepinephrine p-Octopamine p-Tyramine Phenethylamine Serotonin Synephrine Tryptamine; Unknown: RG7351

Antagonists

Selective: EPPTB (RO5212773)

*Note that other phenethylamines, tryptamines, ergolines, and thyronamines are either known to or are likely to act as non-selective TAAR1 agonists as well.

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