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25O-NBOMe

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. It is the N-(2-methoxybenzyl) derivative of 2C-O (2,4,5-trimethoxyphenethylamine).

Column 1
2,4,5-TMPEA-NBOMe; NBOMe-2,4,5-TMPEA; TMPEA-2-NBOMe; NBOMe-TMPEA-2; N-(2-Methoxybenzyl)-2,4,5-trimethoxyphenethylamine
Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}None
IUPAC name
N-[(2-methoxyphenyl)methyl]-2-(2,4,5-trimethoxyphenyl)ethan-1-amine
172213167
C19H25NO4
331.412 g·mol−1
Interactive image
SMILES
COc1cc(OC)c(cc1CCNCc1ccccc1OC)OC
InChI
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,9-10,13H2,1-4H3Key: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. It is the N-(2-methoxybenzyl) derivative of 2C-O (2,4,5-trimethoxyphenethylamine).

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%. It activated the serotonin 5-HT2A receptor with 191- to 309-fold higher potency than 2C-O in vitro. 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. For comparison, in other studies in mice, the ED50 of 25I-NBOMe was 0.078 mg/kg (9-fold lower) and of 25D-NBOMe was 0.23 mg/kg (3-fold lower).

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

  • 25-NB

  • 25H-NBOMe

  • TMA-2

  • 2,4,6-TMPEA-NBOMe

  • 25O-NBOMe - Isomer Design

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