25I-NBOH

25I-NBOH
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C17H20INO3
Molar mass 413.249 g/mol
3D model (JSmol)
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25I-NBOH (NBOH-2CI, Cimbi-27, 2-C-I-NBOH) is a derivative of the phenethylamine derived hallucinogen 2C-I that was discovered in 2006 by a team at Purdue University. It acts as a potent agonist for the 5HT2A receptor,[1][2] with a Ki of 0.061nM at the human 5HT2A receptor, similar to the better-known compound 25I-NBOMe, making it some twelve times the potency of 2C-I itself. In vitro tests showed this compound acted as an agonist but animal studies have not been reported. While the N-benzyl derivatives of 2C-I were significantly increased in binding activity to 5HT2A receptor fragments, compared to 2C-I, the N-benzyl derivatives of DOI were less active, compared to DOI.[3]

25I-NBOH is notable as one of the most selective agonist ligands for the 5-HT2A receptor with an EC50 value of 0.074 nM and more than 400x selectivity over the 5-HT2C receptor.[4]

Legality

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.[5]

Analogues and derivatives

Analogues and derivatives of 2C-I:

25I-NB*:

References

  1. ↑ Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–693. PMID 21174090. doi:10.1007/s00259-010-1686-8.
  2. ↑ Silva, M. E.; Heim, R.; Strasser, A.; Elz, S.; Dove, S. (2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor". Journal of Computer-aided Molecular Design. 25 (1): 51–66. PMID 21088982. doi:10.1007/s10822-010-9400-2.
  3. ↑ Braden, M. R.; Parrish, J. C.; Naylor, J. C.; Nichols, D. E. (2006). "Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists". Molecular Pharmacology. 70 (6): 1956–1964. PMID 17000863. doi:10.1124/mol.106.028720.
  4. ↑ Hansen, M.; Phonekeo, K.; Paine, J. S.; Leth-Petersen, S.; Begtrup, M.; Bräuner-Osborne, H.; Kristensen, J. L. (2014). "Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–9. PMC 3963123 Freely accessible. PMID 24397362. doi:10.1021/cn400216u.
  5. ↑ https://lakemedelsverket.se/upload/lvfs/HSLF_FS_2015_12.pdf
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