2C2-NBOMe

Last updated
2C2-NBOMe
2C2-NBOMe structure.png
Clinical data
Other namesNBOMe-MMDPEA-2; MMDPEA-2-NBOMe; 2C-MMDA-2-NBOMe; 2C-2-NBOMe; N-(2-Methoxybenzyl)-2-methoxy-4,5-methylenedioxyphenethylamine
Drug class Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • N-(2-methoxybenzyl)-1-(2-methoxy-4,5-methylenedioxyphenyl)-2-aminoethane
Chemical and physical data
Formula C18H21NO4
Molar mass 315.369 g·mol−1
3D model (JSmol)
  • COc1ccccc1CNCCc1cc2OCOc2cc1OC
  • 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, also known as 2C-MMDA-2-NBOMe or NBOMe-MMDPEA-2, is a phenethylamine derivative from the 25-NB (NBOMe) family. [1] [2] It is the NBOMe derivative of 2C-MMDA-2 (MMDPEA-2). [2]

Contents

It acts as a potent agonist at the serotonin 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. [1] [2]

It is related in structure to psychedelic phenethylamine derivatives such as MMDA-2 and lophophine (MMDPEA) 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]

The drug was first described in the literature by Jason Wallach and colleagues in 2022 and 2023. [1] [2]

See also

References

  1. 1 2 3 4 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. 1 2 3 4 5 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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