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o-Phenyl-3-iodotyramine
Identifiers
	IUPAC name 2-(3-Iodo-4-phenoxyphenyl)ethanamine;
CAS Number	794507-61-2 ;
PubChem CID	11501691;
ChemSpider	9676493;
UNII	H3WFC2TGK2;
CompTox Dashboard (EPA)	DTXSID401030333 ;
Chemical and physical data
Formula	C14H14INO
Molar mass	339.176 g·mol−1
3D model (JSmol)	Interactive image;
	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 (December 2006). "Trace amine-associated receptors and their ligands". British Journal of Pharmacology. 149 (8): 967–78. doi:10.1038/sj.bjp.0706948. PMC 2014643. PMID 17088868.
^ Ledonne A, Federici M, Giustizieri M, Pessia M, Imbrici P, Millan MJ, et al. (July 2010). "Trace amines depress D(2)-autoreceptor-mediated responses on midbrain dopaminergic cells". British Journal of Pharmacology. 160 (6): 1509–20. doi:10.1111/j.1476-5381.2010.00792.x. PMC 2938821. PMID 20590640.
^ Revel FG, Moreau JL, Gainetdinov RR, Bradaia A, Sotnikova TD, Mory R, et al. (May 2011). "TAAR1 activation modulates monoaminergic neurotransmission, preventing hyperdopaminergic and hypoglutamatergic activity". Proceedings of the National Academy of Sciences of the United States of America. 108 (20): 8485–90. Bibcode:2011PNAS..108.8485R. doi:10.1073/pnas.1103029108. PMC 3101002. PMID 21525407.
^ Di Cara B, Maggio R, Aloisi G, Rivet JM, Lundius EG, Yoshitake T, et al. (November 2011). "Genetic deletion of trace amine 1 receptors reveals their role in auto-inhibiting the actions of ecstasy (MDMA)". The Journal of Neuroscience. 31 (47): 16928–40. doi:10.1523/JNEUROSCI.2502-11.2011. PMC 6623861. PMID 22114263.

[1] Zucchi R, Chiellini G, Scanlan TS, Grandy DK (December 2006). "Trace amine-associated receptors and their ligands". British Journal of Pharmacology. 149 (8): 967–78. doi:10.1038/sj.bjp.0706948. PMC 2014643. PMID 17088868.

[2] Ledonne A, Federici M, Giustizieri M, Pessia M, Imbrici P, Millan MJ, et al. (July 2010). "Trace amines depress D(2)-autoreceptor-mediated responses on midbrain dopaminergic cells". British Journal of Pharmacology. 160 (6): 1509–20. doi:10.1111/j.1476-5381.2010.00792.x. PMC 2938821. PMID 20590640.

[3] Revel FG, Moreau JL, Gainetdinov RR, Bradaia A, Sotnikova TD, Mory R, et al. (May 2011). "TAAR1 activation modulates monoaminergic neurotransmission, preventing hyperdopaminergic and hypoglutamatergic activity". Proceedings of the National Academy of Sciences of the United States of America. 108 (20): 8485–90. Bibcode:2011PNAS..108.8485R. doi:10.1073/pnas.1103029108. PMC 3101002. PMID 21525407.

[4] Di Cara B, Maggio R, Aloisi G, Rivet JM, Lundius EG, Yoshitake T, et al. (November 2011). "Genetic deletion of trace amine 1 receptors reveals their role in auto-inhibiting the actions of ecstasy (MDMA)". The Journal of Neuroscience. 31 (47): 16928–40. doi:10.1523/JNEUROSCI.2502-11.2011. PMC 6623861. PMID 22114263.

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Identifiers

IUPAC name 2-(3-Iodo-4-phenoxyphenyl)ethanamine
CAS Number	794507-61-2^Y
PubChem CID	11501691
ChemSpider	9676493
UNII	H3WFC2TGK2
CompTox Dashboard (EPA)	DTXSID401030333
Chemical and physical data
Formula	C₁₄H₁₄INO
Molar mass	339.176 g·mol⁻¹
3D model (JSmol)	Interactive image
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