25N-N1-Nap 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-N1-Nap is a biased agonist, producing robust activation of 5-HT2A coupled signalling pathways mediated by beta arrestin 2, but with little or no activation of pathways mediated via Gq. In animal studies it produces antipsychotic effects but without producing the head-twitch response associated with psychedelic activity.[1][2]

25N-N1-Nap
Identifiers
  • N-[(naphthalen-1-yl)methyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane
Chemical and physical data
FormulaC21H22N2O4
Molar mass366.417 g·mol−1
3D model (JSmol)
  • COc1cc(CCNCc2cccc3ccccc32)c(cc1[N+]([O-])=O)OC
  • InChI=1S/C21H22N2O4/c1-26-20-13-19(23(24)25)21(27-2)12-16(20)10-11-22-14-17-8-5-7-15-6-3-4-9-18(15)17/h3-9,12-13,22H,10-11,14H2,1-2H3
  • Key:ALVHBRTUOXXMDK-UHFFFAOYSA-N

See also

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References

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  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.