o-Phenyl-3-iodotyramine

o-Phenyl-3-iodotyramine
Systematic (IUPAC) name

2-(3-Iodo-4-phenoxyphenyl)ethanamine
Identifiers
PubChem	CID 11501691
ChemSpider	9676493
Chemical data
Formula	C₁₄H₁₄INO
Molar mass	339.171 g/mol
SMILES Ic1cc(CCN)ccc1Oc2ccccc2
InChI 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

↑ 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

TAAR ligands in humans

TAAR1

Agonists

Endogenous^†	Classical monoamine neurotransmitters Dopamine Histamine Norepinephrine Serotonin Trace amines 3-Iodothyronamine 3-Methoxytyramine N-Methylphenethylamine N-Methyltyramine m-Octopamine p-Octopamine Phenethylamine Phenylethanolamine Synephrine Tryptamine m-Tyramine p-Tyramine

Synthetic^‡	Amphetamine DOB DOET 4-Hydroxyamphetamine Isoprenaline MDA MDMA 2-Methylphenethylamine 3-Methylphenethylamine 4-Methylphenethylamine β-Methylphenethylamine Methamphetamine 3-MMA Norfenfluramine Phentermine o-PIT Propylhexedrine RO5166017

Antagonists

EPPTB (RO5212773)

TAAR2

Agonists^‡	3-Iodothyronamine Phenethylamine Tyramine

Antagonists

TAAR5

Agonists^‡	Dimethylethylamine Trimethylamine

Antagonists^‡	3-Iodothyronamine

^†References for all endogenous human TAAR1 ligands are provided at List of trace amines

^‡References for synthetic TAAR1 agonists can be found at TAAR1 or in the associated compound articles. For TAAR2 and TAAR5 agonists and antagonists, see TAAR for references.

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