25I-NBOH
Chemical compound
From Wikipedia, the free encyclopedia
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[3][4] and has also been encountered as a novel designer drug.[4][5]
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| Other names | NBOH-2-CI; Cimbi-27; 2C-I-NBOH; N-(2-Hydroxybenzyl)-4-iodo-2,5-dimethoxyphenethylamine |
| Routes of administration | Sublingual, buccal[1] |
| Drug class | Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen |
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| Formula | C17H20INO3 |
| Molar mass | 413.255 g·mol−1 |
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Use and effects
The dose range of 25I-NBOH is 300 to 1,000 μg, with an estimated typical dose of 700 μg.[1][5] The route of administration is sublingual or buccal.[1]
Interactions
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 2,220–>10,000 (Ki) 37,000 (EC50) 74% (Emax) |
| 5-HT1B | 2,446 |
| 5-HT1D | 1,277 |
| 5-HT1E | >10,000 |
| 5-HT1F | ND |
| 5-HT2A | 0.061–1.12 (Ki) 0.074–1.52 (EC50) 86–136% (Emax) |
| 5-HT2B | 1.9–2.8 (Ki) 111 (EC50) 21% (Emax) |
| 5-HT2C | 0.13–1.4 (Ki) 2.4–32 (EC50) 94–101% (Emax) |
| 5-HT3 | >10,000 |
| 5-HT4 | ND |
| 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 | ND |
| D1 | ND |
| D2 | >10,000 |
| D3 | 678 |
| D4 | 844 |
| D5 | >10,000 |
| H1, H2 | ND |
| H3 | >10,000 |
| H4 | ND |
| M1–M5 | >10,000 |
| I1 | ND |
| σ1 | 160 |
| σ2 | 264 |
| MOR | 47 (Ki) 1,330–23,400 (EC50) 16–55% (Emax) |
| DOR | ND |
| KOR | 328 |
| TAAR1 | ND |
| SERT | 1,155–1,220 (Ki) 1,720 (IC50) Inactive (EC50) |
| NET | 4,060 (Ki) 629 (IC50) Inactive (EC50) |
| DAT | 8,500 (Ki) 30,700 (IC50) Inactive (EC50) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [6][7][8][9][10][11][12] [13][3][14][15][16][17] | |
25I-NBOH acts as a potent agonist of the 5-HT2A receptor,[18][19] 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.[20]
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 0.074 nM and with more than 400-fold selectivity over the serotonin 5-HT2C receptor.[16][12] However, in another study, it only had about 6-fold selectivity for the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor.[14]
25I-NBOH produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[1]
Chemistry
Analysis
25I-NBOH is a labile molecule which fragments into 2C-I when analyzed by routine gas chromatography (GC) methods.[21] A specific method for reliable identification of 25I-NBOH using GC/MS has been reported, allowing forensic forces worldwide to correctly identify this compound.[22]
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.[23][24][25]
Society and culture
Legal status
Canada
25I-NBOH is a controlled substance in Canada under phenethylamine blanket-ban language.[26]
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".[27]
United Kingdom
This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971.[28]
United States
25I-NBOH is not an explicitly controlled substance in the United States.[29] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.