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  Y
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]}

See also

• 25-NB
• Non-hallucinogenic 5-HT_2A receptor agonist
• 25N-NBOMe (NBOMe-2C-N)
• 25N-N1-Nap
• RS130-180

References

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 
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. doi:10.1101/2023.07.29.551106. PMC   10418054 . PMID   37577474.
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. doi:10.1038/s41467-023-44016-1. PMC   10724237 . PMID   38102107.