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25O-NBOMe

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25O-NBOMe
Clinical data
Other names2,4,5-TMPEA-NBOMe; NBOMe-2,4,5-TMPEA; TMPEA-2-NBOMe; NBOMe-TMPEA-2; N-(2-Methoxybenzyl)-2,4,5-trimethoxyphenethylamine
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • N-[(2-methoxyphenyl)methyl]-2-(2,4,5-trimethoxyphenyl)ethan-1-amine
PubChem CID
Chemical and physical data
FormulaC19H25NO4
Molar mass331.412 g·mol−1
3D model (JSmol)
  • COc1cc(OC)c(cc1CCNCc1ccccc1OC)OC
  • InChI=1S/C19H25NO4/c1-21-16-8-6-5-7-15(16)13-20-10-9-14-11-18(23-3)19(24-4)12-17(14)22-2/h5-8,11-12,20H,9-10,13H2,1-4H3
  • Key:YWHPPSGTTPXYSD-UHFFFAOYSA-N

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 EC50Tooltip half-maximal effective concentration of 1.02 to 7.24 nM and an EmaxTooltip maximal efficacy 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 ED50Tooltip median effective dose 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]

See also

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References

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  1. ^ a b c Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-aided Molecular Design. 25 (1): 51–66. doi:10.1007/s10822-010-9400-2. PMID 21088982.
  2. ^ a b c d 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. ^ a b c d e Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nature Communications. 14 (1): 8221. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.
  4. ^ Halberstadt AL, Geyer MA (February 2014). "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. doi:10.1016/j.neuropharm.2013.08.025. PMC 3866097. PMID 24012658.
  5. ^ Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology. 167: 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152.
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