25N-NBOMe

25N-NBOMe, also known as 2C-N-NBOMe or 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.

Use and effects

The dose range of 25N-NBOMe has been given as 0.1 to 1.3mg or more sublingually, with a typical dose estimate of 0.6mg. Whereas 2C-N is much less potent in terms of dose than other 2C drugs, 25N-NBOMe appears to have a similar dose range as other NBOMe drugs.

Pharmacology

Pharmacodynamics

25N-NBOMe is a selective and highly potent agonist of the serotonin 5-HT₂ receptors. Its affinities are 0.144nM at the serotonin 5-HT_2A receptor, 8.7nM at the serotonin 5-HT_2B receptor, and 1.06nM at the serotonin [5-HT2C receptor|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 values of 25N-NBOMe are 0.51nM at the serotonin 5-HT_2A receptor, 47nM at the serotonin 5-HT_2B receptor, and 1.32nM 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.
In a 2023 study, the pharmacological properties of 25N-NBOMe were extensively characterized using both in vitro and in vivo models. Radioligand binding assays showed high binding affinity for serotonin 5-HT₂ receptors, with pK_i values of 9.26 ± 0.15 at 5-HT_2A, 8.35 ± 0.08 at 5-HT_2B, and 8.16 ± 0.07 at 5-HT_2C. The compound was also screened across more than 40 additional CNS targets and found to be highly selective for the 5-HT₂ receptor subfamily.
In calcium flux functional assays, 25N-NBOMe was a potent full agonist at 5-HT_2A and 5-HT_2C receptors, while showing negligible agonist activity at 5-HT_2B.
Bioluminescence [resonance energy transfer] functional assays measuring Gq dissociation and β-arrestin2 recruitment signaling indicated strong agonist activity at 5-HT_2A, with Gq pEC₅₀ = 9.69 ± 0.04 and β-arrestin2 recruitment pEC₅₀ = 9.66 ± 0.09. This illustrates that 25N-NBOMe is a balanced 5-HT_2A agonist across these pathways, in contrast to analogs like 25N-N1-Nap and 25N-NBPh which displayed functional selectivity or signaling bias for β-arrestin2 recruitment. For 5-HT_2C, Gq pEC₅₀ was 9.34 ± 0.08, while weak partial agonist activity was observed at 5-HT_2B.
In vivo, 25N-NBOMe induced a robust head-twitch response in mice with an ED₅₀ of 0.11 mg/kg. Notably 25N-NBOMe produced the highest HTR frequency among a panel of structurally related 25N analogs.
Unlike many other serotonergic psychedelics, 25N-NBOMe has shown reinforcing effects in rodents, including in terms of conditioned place preference and self-administration. 25N-NBOMe has been found to increase phosphorylation of the dopamine transporter 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.

History

25N-NBOMe was first described in the scientific literature by 2012.

Society and culture

Legal status

Canada

25N-NBOMe is a controlled substance in Canada under phenethylamine blanket-ban language.

Hungary

25N-NBOMe is illegal in Hungary.

Sweden

added 25N-NBOMe to Narcotic Drugs Punishments Act under swedish schedule I as of January 16, 2015, published by Medical Products Agency (MPA) in regulation LVFS 2014:11 listed as 25N-NBOMe, and 2--N-etanamin.

United States

25N-NBOMe is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.
25N-NBOMe is illegal in Alabama.