o-Phenyl-3-iodotyramine

o-Phenyl-3-iodotyramine
Identifiers

IUPAC name 2-(3-Iodo-4-phenoxyphenyl)ethanamine
CAS Number	794507-61-2^Y
PubChem CID	11501691
ChemSpider	9676493
UNII	H3WFC2TGK2
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.

Human trace amine-associated receptor ligands

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 (tenamfetamine) MDMA (midomafetamine) 2-Methylphenethylamine 3-Methylphenethylamine 4-Methylphenethylamine β-Methylphenethylamine Methamphetamine 3-MMA Norfenfluramine Phentermine o-PIT Propylhexedrine Ralmitaront (RG-7906, RO-6889450) RO5166017 N,N-Dimethylphenethylamine Ulotaront (SEP-363856)

Neutral antagonists

Inverse agonists

EPPTB (RO5212773)

TAAR2

Agonists^‡
Neutral antagonists

TAAR5

Agonists^‡	N,N-Dimethylethylamine Trimethylamine
Neutral antagonists
Inverse agonists^‡	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 inverse agonists, see TAAR for references.

See also: Receptor/signaling modulators

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This page was last edited on 11 November 2023, at 21:25

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References