25I-NBOH

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.

25I-NBOH
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H20INO3
Molar mass413.255 g·mol−1
3D model (JSmol)
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Pharmacology

25I-NBOH acts as a potent agonist for the 5HT2A receptor,[1][2] with a Ki of 0.061 nM at the human 5HT2A 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 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 with more than 400 times selectivity over the 5-HT2C receptor.[4]

Analytical chemistry

25I-NBOH is a labile molecule which fragments into 2C-I when analyzed by routine gas chromatography (GC) methods.[5] A specific method for reliable identification of 25I-NBOH using GC/MS has been reported, allowing forensic forces worldwide to correctly identify this compound.[6]

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".[7]

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.[8]

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. doi:10.1007/s00259-010-1686-8. PMID 21174090.
  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. Bibcode:2011JCAMD..25...51S. CiteSeerX 10.1.1.688.2670. doi:10.1007/s10822-010-9400-2. PMID 21088982.
  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. doi:10.1124/mol.106.028720. PMID 17000863.
  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. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.
  5. Arantes, Luciano Chaves; Júnior, Ettore Ferrari; De Souza, Luciano Figueiredo; Cardoso, Andriele Costa; Alcântara, Thaynara Lino Fernandes; Lião, Luciano Morais; Machado, Yuri; Lordeiro, Rogério Araújo; Neto, José Coelho; Andrade, Ana Flávia B (2017). "25I-NBOH: A new potent serotonin 5-HT2A receptor agonist identified in blotter paper seizures in Brazil". Forensic Toxicology. 35 (2): 408–414. doi:10.1007/s11419-017-0357-x. PMC 5486617. PMID 28706567.
  6. Coelho Neto, José; Andrade, Ana Flávia B; Lordeiro, Rogério Araújo; Machado, Yuri; Elie, Mathieu; Ferrari Júnior, Ettore; Arantes, Luciano Chaves (2017). "Preventing misidentification of 25I-NBOH as 2C-I on routine GC–MS analyses" (PDF). Forensic Toxicology. 35 (2): 415. doi:10.1007/s11419-017-0362-0.
  7. "Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkeme del, folkhälsa m.m." (PDF).
  8. "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
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