25N-NBPh
Identifiers
  • N-[(2-phenyl)benzyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane
Chemical and physical data
FormulaC23H24N2O4
Molar mass392.455 g·mol−1
3D model (JSmol)
  • COc1cc(CCNCc2ccccc2c2ccccc2)c(cc1[N+]([O-])=O)OC
  • 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-HT2A receptor with weaker activity at 5-HT2B and 5-HT2C. 25N-NBPh is a biased agonist, producing robust activation of 5-HT2A coupled signalling pathways mediated by beta arrestin 2, but with only slight activation of pathways mediated via Gq. 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

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-HT2A Receptor Signaling Pathways Responsible for Psychedelic Potential". bioRxiv. doi:10.1101/2023.07.29.551106. PMC 10418054. PMID 37577474.
  3. ↑ Wallach, J., Cao, A.B., Calkins, M.M. et al. Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential. Nat Commun 2023; 14, 8221. doi:10.1038/s41467-023-44016-1


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