2C2-NBOMe

2C2-NBOMe
Identifiers
IUPAC name
  • N-(2-methoxybenzyl)-1-(2-methoxy-4,5-methylenedioxyphenyl)-2-aminoethane
Chemical and physical data
FormulaC18H21NO4
Molar mass315.369 g·mol−1
3D model (JSmol)
SMILES
  • COc1ccccc1CNCCc1cc2OCOc2cc1OC
InChI
  • InChI=1S/C18H21NO4/c1-20-15-6-4-3-5-14(15)11-19-8-7-13-9-17-18(23-12-22-17)10-16(13)21-2/h3-6,9-10,19H,7-8,11-12H2,1-2H3
  • Key:XPZZCRFMAACBFQ-UHFFFAOYSA-N

2C2-NBOMe (NBOMe-MMDPEA-2) is a phenethylamine derivative from the 25-NB class. It acts as a potent agonist at the 5-HT2A receptor with weaker activity at 5-HT2B and 5-HT2C, and produces a head-twitch response in animal studies which often correlates with potential for psychedelic effects in humans. It is related in structure to psychedelic amphetamine derivatives such as MMDA-2 and is the first phenethylamine derivative with a methylenedioxy substitution on the phenyl ring but no alkyl substitution on the alpha carbon, that has been shown to produce psychedelic-appropriate responding in animals.[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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