Chemistry:25O-NBOMe

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25O-NBOMe, also known as 2,4,5-TMPEA-NBOMe or as N-(2-methoxybenzyl)-2,4,5-trimethoxyphenethylamine, is a serotonin receptor modulator and putative psychedelic drug of the phenethylamine and 25-NB (NBOMe) families.[1][2][3] It is the N-(2-methoxybenzyl) derivative of 2C-O (2,4,5-trimethoxyphenethylamine).[1][2][3]

The drug is known to act as a serotonin 5-HT2A receptor partial agonist, with an EC50 of 1.02 to 7.24 nM and an Emax of 57 to 129%.[1][2][3] It activated the serotonin 5-HT2A receptor with 191- to 309-fold higher potency than 2C-O in vitro.[3] 25O-NBOMe robustly and dose-dependently induces the head-twitch response, a behavioral proxy of psychedelic effects, in mice, with an ED50 of 0.70 mg/kg.[3] For comparison, in other studies in mice, the ED50 of 25I-NBOMe was 0.078 mg/kg (9-fold lower)[4] and of 25D-NBOMe was 0.23 mg/kg (3-fold lower).[5]

25O-NBOMe was first described in the scientific literature by 2009.[2] It is a controlled substance in Canada under phenethylamine blanket-ban language.[6]

See also

References

  1. ↑ 1.0 1.1 1.2 "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-aided Molecular Design 25 (1): 51–66. January 2011. doi:10.1007/s10822-010-9400-2. PMID 21088982. Bibcode: 2011JCAMD..25...51S. 
  2. ↑ 2.0 2.1 2.2 2.3 Silva ME (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (Thesis). doi:10.5283/EPUB.12119. Retrieved 9 June 2025.
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nature Communications 14 (1). December 2023. doi:10.1038/s41467-023-44016-1. PMID 38102107. Bibcode: 2023NatCo..14.8221W. 
  4. ↑ "Effects of the hallucinogen 2,5-dimethoxy-4-iodophenethylamine (2C-I) and superpotent N-benzyl derivatives on the head twitch response". Neuropharmacology 77: 200–207. February 2014. doi:10.1016/j.neuropharm.2013.08.025. PMID 24012658. 
  5. ↑ "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology 167. May 2020. doi:10.1016/j.neuropharm.2019.107933. PMID 31917152. 
  6. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 





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