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 effects consistent with a "partial psychedelic" profile, producing a modest head-twitch response when administered by itself, but blocking the effects of the fully active psychedelic DOI. Such compounds are expected to be useful in medical applications where the psychedelic experience is considered to be an important component of the therapeutic effect, but it is desirable to limit the scope of the effects produced so as to minimise the chance of "bad trip" type negative experiences which may be counterproductive to the intended therapeutic aims.[1][2]

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.


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