25N-NBPh

25N-NBPh
Clinical data
Other names	NBPh-2C-N
Identifiers
	IUPAC name N-[(2-phenyl)benzyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane;
CAS Number	2865185-29-9 ;
PubChem CID	175819744;
Chemical and physical data
Formula	C23H24N2O4
Molar mass	392.455 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1cc(CCNCc2ccccc2c2ccccc2)c(cc1[N+]([O-])=O)OC;
	InChI InChI=1S/C23H24N2O4/c1-28-22-15-21(25(26)27)23(29-2)14-18(22)12-13-24-16-19-10-6-7-11-20(19)17-8-4-3-5-9-17/h3-11,14-15,24H,12-13,16H2,1-2H3; Key:LXUVMUYFLPADGJ-UHFFFAOYSA-N;

25N-NBPh (NBPh-2C-N) is a phenethylamine derivative from the 25-NB class, which acts as a potent agonist at the 5-HT_2A receptor with weaker activity at 5-HT_2B and 5-HT_2C. 25N-NBPh is a biased agonist, producing robust activation of 5-HT_2A coupled signalling pathways mediated by beta arrestin 2, but with only slight activation of pathways mediated via G_q. In animal studies it produces a modest head-twitch response when administered by itself, but blocks the effects of the fully active psychedelic DOI.^[1]^[2]^[3]

References

^ WO 2022241006, Wallach J, McCorvy J, Halberstadt A, "Selective, Partial and Arrestin-Biased 5-HT2A Agonists with Utility in Various Disorders.", published 17 November 2022, assigned to Saint Joseph's University, The Medical College Of Wisconsin, Inc., The Regents Of The University Of California
^ Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (July 2023). "Identification of 5-HT_2A Receptor Signaling Pathways Responsible for Psychedelic Potential". bioRxiv 10.1101/2023.07.29.551106.
^ Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (December 2023). "Identification of 5-HT_2A receptor signaling pathways associated with psychedelic potential". Nature Communications. 14 (1) 8221. Bibcode:2023NatCo..14.8221W. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.

[1] WO 2022241006, Wallach J, McCorvy J, Halberstadt A, "Selective, Partial and Arrestin-Biased 5-HT2A Agonists with Utility in Various Disorders.", published 17 November 2022, assigned to Saint Joseph's University, The Medical College Of Wisconsin, Inc., The Regents Of The University Of California

[Wallach_2023-2] Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (July 2023). "Identification of 5-HT_2A Receptor Signaling Pathways Responsible for Psychedelic Potential". bioRxiv 10.1101/2023.07.29.551106.

[3] Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (December 2023). "Identification of 5-HT_2A receptor signaling pathways associated with psychedelic potential". Nature Communications. 14 (1) 8221. Bibcode:2023NatCo..14.8221W. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.

[1]

[2]

[3]

See also

References