trans-3-(4-Methoxyphenyl)-N-(pentan-3-yl)acrylamide

*trans*-3-(4-Methoxyphenyl)-N-(pentan-3-yl)acrylamide
Names
	Other names TMPPAA
Identifiers
CAS Number	844900-50-1;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3718075;
ChemSpider	777905;
EC Number	110-715-0;
PubChem CID	889955;
	InChI InChI=1S/C15H21NO2/c1-4-13(5-2)16-15(17)11-8-12-6-9-14(18-3)10-7-12/h6-11,13H,4-5H2,1-3H3,(H,16,17)/b11-8+ Key: SPXCFGAFVLQEJK-DHZHZOJOSA-N;
	SMILES CCC(CC)NC(=O)/C=C/C1=CC=C(C=C1)OC;
Properties
Chemical formula	C15H21NO2
Molar mass	247.338 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P317, P330, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

trans-3-(4-Methoxyphenyl)-N-(pentan-3-yl)acrylamide, commonly referred as TMPPAA, is a allosteric agonist and positive allosteric modulator (PAM) of 5-HT₃ receptor. It has the molecular formula C₁₅H₂₁NO₂. TMPPAA behaves as both an agonist and a PAM at 5-HT3A receptors, not via binding at the orthosteric site.^[1]

Pharmacology and mechanism of action

It is a synthetic compound that functions as an allosteric agonist and positive allosteric modulator of the 5-HT3 serotonin receptor. While traditional ligands bind to the extracellular orthosteric site, chimeric and mutational studies indicate that TMPPAA interacts directly with the receptor's transmembrane domain. Electrophysiological experiments show that the compound exhibits distinct desensitization kinetics and causes a progressive current run-down, demonstrating a mechanism of activation separate from serotonin.^[1]^[2]

References

1 2 "Merck-TMPPAA".
↑ Gasiorek, Agnes; Trattnig, Sarah M.; Ahring, Philip K.; Kristiansen, Uffe; Frølund, Bente; Frederiksen, Kristen; Jensen, Anders A. (June 2016). "Delineation of the functional properties and the mechanism of action of TMPPAA, an allosteric agonist and positive allosteric modulator of 5-HT₃ receptors". Biochemical Pharmacology. 110–111: 92–108. doi:10.1016/j.bcp.2016.04.004. PMID 27086281.

[:0-1] 1 2 "Merck-TMPPAA".

[2] Gasiorek, Agnes; Trattnig, Sarah M.; Ahring, Philip K.; Kristiansen, Uffe; Frølund, Bente; Frederiksen, Kristen; Jensen, Anders A. (June 2016). "Delineation of the functional properties and the mechanism of action of TMPPAA, an allosteric agonist and positive allosteric modulator of 5-HT₃ receptors". Biochemical Pharmacology. 110–111: 92–108. doi:10.1016/j.bcp.2016.04.004. PMID 27086281.

[1]

[2]