25I-NBOH

25I-NBOH, also known as N-(2-hydroxybenzyl)-4-iodo-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine, 2C, and N-benzylphenethylamine families related to 2C-I and 25I-NBOMe. It was discovered in 2006 by a team at Purdue University. The drug is a known metabolite of 25I-NBOMe and has also been encountered as a novel designer drug.

Use and effects The dose range of 25I-NBOH is 300 to 1,000μg, with an estimated typical dose of 700μg. The route of administration is sublingual or buccal.

Interactions

Pharmacology Pharmacodynamics + Target Affinity (Ki, nM) 5-HT1A 2,220–>10,000 (Ki)37,000 ()74% () 5-HT1B 2,446 5-HT1D 1,277 5-HT1E >10,000 5-HT1F 5-HT2A 0.061–1.12 (Ki)0.074–1.52 ()86–136% () 5-HT2B 1.9–2.8 (Ki)111 ()21% () 5-HT2C 0.13–1.4 (Ki)2.4–32 ()94–101% () 5-HT3 >10,000 5-HT4 5-HT5A 965 5-HT6 111 5-HT7 3,472 α1A 3,924 α1B >10,000 α1D >10,000 α2A 2,257 α2B 3,043 α2C 1,003 β1 1,088 β2, β3 D1 D2 >10,000 D3 678 D4 844 D5 >10,000 H1, H2 H3 >10,000 H4 M1–M5 >10,000 I1 σ1 160 σ2 264 47 (Ki)1,330–23,400 ()16–55% () 328 1,155–1,220 (Ki)1,720 () () 4,060 (Ki)629 () () 8,500 (Ki)30,700 () () Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: Ettrup, A. (2010). Serotonin receptor studies in the pig brain: pharmacological intervention and positron emission tomography tracer development (Doctoral dissertation, Faculty of Health Sciences, University of Copenhagen). https://research.regionh.dk/en/publications/serotonin-receptor-studies-in-the-pig-brain-pharmacological-inter

25I-NBOH acts as a potent agonist of the 5-HT2A receptor, with a Ki of 0.061 nM at the human 5-HT2A 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-HT2A 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-HT2A receptor known, with an EC50 value of 0.074nM and with more than 400-fold selectivity over the serotonin 5-HT2C receptor. However, in another study, it only had about 6-fold selectivity for the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor.

25I-NBOH produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.

Chemistry Analysis 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 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.

History 25I-NBOH was first described in the scientific literature by Ralm Heim and colleagues by 2000.

Society and culture Legal status Canada 25I-NBOH is a controlled substance in Canada under phenethylamine blanket-ban language.

Sweden 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".

United Kingdom

United States 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.

25I-NBOH

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