EPPTB

EPPTB
Identifiers

IUPAC name N-(3-ethoxyphenyl)-4-pyrrolidin-1-yl-3-trifluoromethylbenzamide
PubChem CID	25175634
ChemSpider	26387935
Chemical and physical data
Formula	C₂₀H₂₁F₃N₂O₂
Molar mass	378.387 g/mol
3D model (JSmol)	Interactive image Interactive image
SMILES CCOc2cc(ccc2)NC(=O)c(cc1C(F)(F)F)ccc1N3CCCC3 CCOc1cccc(c1)NC(=O)c2ccc(c(c2)C(F)(F)F)N3CCCC3
InChI InChI=1S/C20H21F3N2O2/c1-2-27-16-7-5-6-15(13-16)24-19(26)14-8-9-18(25-10-3-4-11-25)17(12-14)20(21,22)23/h5-9,12-13H,2-4,10-11H2,1H3,(H,24,26) Key:KLFVWQCQUXXLOU-UHFFFAOYSA-N

EPPTB (RO-5212773) is a drug developed by Hoffmann-La Roche which acts as a potent and selective inverse agonist of trace amine-associated receptor 1 (TAAR1), with no significant activity at other targets. EPPTB is one of the first selective antagonists developed for TAAR1, and has been used to demonstrate an important role for TAAR1 in regulation of dopaminergic signalling in the limbic system.^[1] Unfortunately while EPPTB has high affinity for the mouse TAAR1, it has much lower affinity for rat and human TAAR1, which limits its use in research.^[2] While the human and mouse forms of TAAR1 have similar functions and bind similar ligands, the actual binding affinities of individual ligands often vary significantly between the two versions of the receptor.^[3]

References

↑ Bradaia A, Trube G, Stalder H, Norcross RD, Ozmen L, Wettstein JG, Pinard A, Buchy D, Gassmann M, Hoener MC, Bettler B. The selective antagonist EPPTB reveals TAAR1-mediated regulatory mechanisms in dopaminergic neurons of the mesolimbic system. Proceedings of the National Academy of Sciences USA. 2009 Nov 24;106(47):20081-6. PMID 19892733
↑ Stalder H, Hoener MC, Norcross RD. Selective antagonists of mouse trace amine-associated receptor 1 (mTAAR1): discovery of EPPTB (RO5212773). Bioorganic and Medicinal Chemistry Letters. 2011 Feb 15;21(4):1227-31. PMID 21237643
↑ Hu LA, Zhou T, Ahn J, Wang S, Zhou J, Hu Y, Liu Q. Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands. Biochemical Journal. 2009 Oct 23;424(1):39-45. PMID 19725810

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 MDMA 2-Methylphenethylamine 3-Methylphenethylamine 4-Methylphenethylamine β-Methylphenethylamine Methamphetamine 3-MMA Norfenfluramine Phentermine o-PIT Propylhexedrine RO5166017 N,N-Dimethylphenethylamine

Neutral antagonists

Inverse agonists

EPPTB (RO5212773)

TAAR2

Agonists^‡	3-Iodothyronamine Phenethylamine Tyramine
Neutral antagonists

TAAR5

Agonists^‡	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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