25N-NBOMe

25N-NBOMe (2C-N-NBOMe, NBOMe-2C-N) is a derivative of the hallucinogen 2C-N. The pharmacological properties of 25N-NBOMe have not been described in the scientific literature, but it is believed to act in a similar manner to related compounds such as 25I-NBOMe and 25C-NBOMe, which are potent agonists at the 5HT_2A receptor. 25N-NBOMe has been sold as a street drug and has only been described in the literature in terms of identification by forensic analysis.

Pharmacology

Pharmacodynamics

25N-NBOMe is a selective and highly potent agonist of the serotonin 5-HT₂ receptors. Its affinities (K_i) are 0.144 nM at the serotonin 5-HT_2A receptor, 8.7 nM at the serotonin 5-HT_2B receptor, and 1.06 nM at the serotonin 5-HT_2C receptor. In terms of affinity, the drug has approximately 7.4-fold selectivity for the serotonin 5-HT_2A receptor over the serotonin 5-HT_2C receptor and 60-fold selectivity for the 5-HT_2A receptor over the serotonin 5-HT_2B receptor.

The EC₅₀Tooltip half-maximal effective concentration (E_maxTooltip maximal efficacy) values of 25N-NBOMe are 0.51 nM (87.9%) at the serotonin 5-HT_2A receptor, 47 nM (57.6%) at the serotonin 5-HT_2B receptor, and 1.32 nM (99.4%) at the serotonin 5-HT_2C receptor. Hence, 25N-NBOMe is a full agonist of the serotonin 5-HT_2A and 5-HT_2C receptors and a partial agonist of the serotonin 5-HT_2B receptor. In terms of functional activity, 25N-NBOMe had 2.6-fold selectivity for the serotonin 5-HT_2A receptor over the serotonin 5-HT_2C receptor and 92-fold selectivity for the serotonin 5-HT_2A receptor over the serotonin 5-HT_2C receptor.

Unlike many other serotonergic psychedelics, 25N-NBOMe has shown reinforcing effects in rodents, including in terms of conditioned place preference (CPP) and self-administration. 25N-NBOMe has been found to increase phosphorylation of the dopamine transporter (DAT) in the striatum similarly to methamphetamine in rodents. DAT phosphorylation is associated with dopamine reverse transport and efflux, which in turn increases extracellular dopamine levels.

Interactions

Toxicity and harm potential

Neurotoxic and cardiotoxic actions

Emergency treatment

Legality

United States

25N-NBOMe is illegal in Alabama.

Hungary

25N-NBOMe is illegal in Hungary.

Sweden

The Riksdag added 25N-NBOMe to Narcotic Drugs Punishments Act under swedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of January 16, 2015, published by Medical Products Agency (MPA) in regulation LVFS 2014:11 listed as 25N-NBOMe, and 2-(2,5-dimetoxi-4-nitrofenyl)-N-(2-metoxibensyl)etanamin.