25I-NBOH (NBOH-2C-I, Cimbi-27, 2C-I-NBOH) is a derivative of the phenethylamine-derived hallucinogen 2C-I that was discovered in 2006 by a team at Purdue University. It is a known metabolite of 25I-NBOMe and has also been encountered as a novel designer drug.
The dose range of 25I-NBOH is 300 to 1,000üg, with an estimated typical dose of 700üg. The route of administration is sublingual or buccal.
25I-NBOH acts as a potent agonist of the 5-HT<sub>2A</sub> receptor, with a K<sub>i</sub> of 0.061 nM at the human 5-HT<sub>2A</sub> receptor, similar to the better-known compound 25I-NBOMe, making it some twelve times the potency of 2C-I itself.
Although in vitro tests show this compound acts as an agonist, animal studies to confirm these findings have not been reported. While the N-benzyl derivatives of 2C-I had significantly increased binding to 5-HT<sub>2A</sub> receptor fragments, compared to 2C-I, the N-benzyl derivatives of DOI, such as DOI-NBOMe, were less active compared to DOI.
25I-NBOH is notable in having been found to be one of the most selective agonists of the serotonin 5-HT<sub>2A</sub> receptor known, with an EC<sub>50</sub> value of 0.074nM and with more than 400-fold selectivity over the serotonin 5-HT<sub>2C</sub> receptor. However, in another study, it only had about 6-fold selectivity for the serotonin 5-HT<sub>2A</sub> receptor over the serotonin 5-HT<sub>2C</sub> receptor.
25I-NBOH produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.
25I-NBOH is a labile molecule which fragments into 2C-I when analyzed by routine gas chromatography (GC) methods. A specific method for reliable identification of 25I-NBOH using GC/MS has been reported, allowing forensic forces worldwide to correctly identify this compound.
Analogues of 25I-NBOH include 2C-I, DOI, 25B-NBOH, 25C-NBOH, 25I-NBOMe, 25I-NB3OMe, 25I-NBMD, 25I-NB4OMe, 25I-NB34MD, 25I-NBF, and DOI-NBOMe, among others.
25I-NBOH was first described in the scientific literature by Ralm Heim and colleagues by 2000.
25I-NBOH is a controlled substance in Canada under phenethylamine blanket-ban language.
The Riksdag added 25I-NBOH to Narcotic Drugs Punishments Act under Swedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of August 18, 2015, published by Medical Products Agency MPA) in regulation HSLF-FS 2015:12 listed as "25I-NBOH" and "2-([2-(4-jodo-2,5-dimetoxifenyl)etylamino]metyl)fenol".
25I-NBOH 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.