25I-NBOH (NBOH-2CI, Cimbi-27, 2-C-I-NBOH) is a derivative of the phenethylamine-derived hallucinogen

2C-I 2C-I is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and described in his 1991 book '' PiHKAL'' (''Phenethylamines I Have Known and Loved''). The drug has been used recreationally as psychedelic and ...

that was discovered in 2006 by a team at

Purdue University Purdue University is a public land-grant research university in West Lafayette, Indiana, and the flagship campus of the Purdue University system. The university was founded in 1869 after Lafayette businessman John Purdue donated land and mone ...

Pharmacology

25I-NBOH acts as a potent agonist of the 5HT_2A receptor, with a K_i of 0.061 nM at the human 5HT_2A receptor, similar to the better-known compound 25I-NBOMe, making it some twelve times the potency of 2C-I itself. Although ''

in vitro ''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called " test-tube experiments", these studies in biology ...

'' 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 5HT_2A receptor fragments, compared to 2C-I, the ''N''-benzyl derivatives of DOI were less active compared to DOI. 25I-NBOH is notable as one of the most selective agonist ligands for the 5-HT_2A receptor with an EC₅₀ value of 0.074 nM with more than 400 times selectivity over the 5-HT_2C receptor.

Analytical chemistry

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.

Legality

Sweden

The Riksdag added 25I-NBOH to 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-(

-(4-jodo-2,5-dimetoxifenyl)etylamino The hyphen-minus is the most commonly used type of hyphen, widely used in digital documents. It is the only character that looks like a minus sign or a dash in many character sets such as ASCII or on most keyboards, so it is also used as such. ...

etyl)fenol".

United Kingdom

Analogues and derivatives

References

{{Phenethylamines 25-NB (psychedelics) Designer drugs Iodoarenes Serotonin receptor agonists