25CN-NBOH

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25CN-NBOH
NBOH-2CCN structure.png
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C18H20N2O3
Molar mass 312.362 g/mol
3D model (JSmol)

25CN-NBOH (or NBOH-2C-CN) is a compound indirectly derived from the phenethylamine series of hallucinogens, which was discovered in 2014 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][3] In animal studies, 25CN-NBOH was found to partially substitute for DOI but was considerably weaker at inducing a head-twitch response in mice.[4]

Related compounds[edit]

The tendency of the 4-cyano substitution to confer high 5-HT2A selectivity had previously been observed with DOCN,[5] 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),[6] 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

Legality[edit]

Hungary[edit]

25CN-NBOH is illegal in Hungary.[7]

United Kingdom[edit]

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]


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 3963123Freely accessible. PMID 24397362. 
  2. ^ Jensen, Anders A.; McCorvy, John D.; Leth-Petersen, Sebastian; Bundgaard, Christoffer; Liebscher, Gudrun; Kenakin, Terry P.; Bräuner-Osborne, Hans; Kehler, Jan; Kristensen, Jesper L. (June 2017). "Detailed Characterization of the In Vitro Pharmacological and Pharmacokinetic Properties of N-(2-Hydroxybenzyl)-2,5-Dimethoxy-4-Cyanophenylethylamine (25CN-NBOH), a Highly Selective and Brain-Penetrant 5-HT2A Receptor Agonist". Journal of Pharmacology and Experimental Therapeutics. 361 (3): 441–453. doi:10.1124/jpet.117.239905. PMID 28360333. 
  3. ^ Martin Hansen PhD. Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. University of Copenhagen, 2011.
  4. ^ 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. 2014 Sep 17. PMID 25224567
  5. ^ 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. 
  6. ^ 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. 
  7. ^ A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása
  8. ^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.