25O-NBOMe

25O-NBOMe
Clinical data
Other names	2,4,5-TMPEA-NBOMe; NBOMe-2,4,5-TMPEA; TMPEA-2-NBOMe; NBOMe-TMPEA-2; N-(2-Methoxybenzyl)-2,4,5-trimethoxyphenethylamine
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Identifiers
	IUPAC name N-[(2-methoxyphenyl)methyl]-2-(2,4,5-trimethoxyphenyl)ethan-1-amine;
PubChem CID	172213167;
Chemical and physical data
Formula	C19H25NO4
Molar mass	331.412 g·mol−1
3D model (JSmol)	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,9-10,13H2,1-4H3; 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. It is the N-(2-methoxybenzyl) derivative of 2C-O (2,4,5-trimethoxyphenethylamine).

The drug is known to act as a serotonin 5-HT_2A receptor partial agonist, with an EC₅₀Tooltip half-maximal effective concentration of 1.02 to 7.24 nM and an E_maxTooltip maximal efficacy of 57 to 129%. It activated the serotonin 5-HT_2A 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.