25CN-NBOH

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25CN-NBOH
NBOH-2CCN structure.png
Systematic (IUPAC) name
2-([2-(4-cyano-2,5-dimethoxyphenyl)ethylamino]methyl)phenol
Clinical data
Legal status
  • Uncontrolled
Identifiers
CAS number 1391489-32-9
ATC code ?
Chemical data
Formula C18H20N2O3 
Mol. mass 312.362 g/mol

25CN-NBOH (or NBOH-2C-CN) is a compound indirectly derived from the phenethylamine series of hallucinogens, which was discovered in 2011 by Martin Hansen at the University of Copenhagen. This compound is notable as one of the most selective agonist ligands for the 5-HT2A receptor yet discovered, with a pKi of 8.88 at the human 5-HT2A receptor and with 100x selectivity for 5-HT2A over 5-HT2C, and 46x selectivity for 5-HT2A over 5-HT2B.[1][2] In animal studies, 25CN-NBOH was found to partially substitute for DOI but was considerably weaker at inducing a head-twitch response in mice.[3] The tendency of the 4-cyano substitution to confer high 5-HT2A selectivity had previously been observed with DOCN,[4] but this was not sufficiently potent to be widely adopted as a research ligand. 25CN-NBOH is still slightly less selective for 5-HT2A than the more complex cyclised derivative 2S,6S-DMBMPP ((2S,6S)-2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine),[5] however it is also less complex to synthesise and has higher efficacy as a partial agonist of the 5-HT2A receptor.

(2S,6S)-2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine

See also[edit]

References[edit]

  1. ^ 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.  edit
  2. ^ Martin Hansen PhD. Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. University of Copenhagen, 2011.
  3. ^ Fantegrossi WE, Gray BW, Bailey JM, Smith DA, Hansen M, Kristensen JL. Hallucinogen-like effects of 2-([2-(4-cyano-2,5-dimethoxyphenyl) ethylamino]methyl)phenol (25CN-NBOH), a novel N-benzylphenethylamine with 100-fold selectivity for 5-HT2A receptors, in mice. Psychopharmacology (Berlin). 2014 Sep 17. PMID 25224567
  4. ^ Nelson, D. L.; Lucaites, V. L.; Wainscott, D. B.; Glennon, R. A. (1999). "Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors". Naunyn-Schmiedeberg's Archives of Pharmacology 359: 1. doi:10.1007/PL00005315.  edit
  5. ^ Juncosa, J. I.; Hansen, M.; Bonner, L. A.; Cueva, J. P.; Maglathlin, R.; McCorvy, J. D.; Marona-Lewicka, D.; Lill, M. A.; Nichols, D. E. (2012). "Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands". ACS Chemical Neuroscience 4: 120717095020003. doi:10.1021/cn3000668.  edit