25N-N1-Nap

25N-N1-Nap
Identifiers
IUPAC name
  • N-[(naphthalen-1-yl)methyl]-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane
CAS Number
PubChem CID
Chemical and physical data
FormulaC21H22N2O4
Molar mass366.417 g·mol−1
3D model (JSmol)
SMILES
  • COc1cc(CCNCc2cccc3ccccc32)c(cc1[N+]([O-])=O)OC
InChI
  • 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

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 signaling pathways mediated by beta arrestin 2, but with little or no activation of pathways mediated via Gq. In animal studies it produces antipsychotic-like effects but without producing the head-twitch response associated with psychedelic activity.[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. (2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nature Communications. 14 (1): 8221. doi:10.1186/s12969-023-00927-3. PMC 10694965. PMID 38001451.



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