25B-NBOH
Width250px
Legal brF2
Legal br comment[1]
Legal deNpSG
Legal ukClass A
Cas number1335331-46-8
UniiKHR1SJ9L0Y
Pubchem125181394
Chemspiderid58191433
Iupac name2-({[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenol
C17
H20
Br1
N1
O3
SmilesBrC2=CC(=C(CCNCC1=C(C=CC=C1)O)C=C2OC)OC
Stdinchi1S/C17H20BrNO3/c1-21-16-10-14(18)17(22-2)9-12(16)7-8-19-11-13-5-3-4-6-15(13)20/h3-6,9-10,19-20H,7-8,11H2,1-2H3
StdinchikeyRSUNJYKZRKIBNB-UHFFFAOYSA-N

25B-NBOH (2C-B-NBOH, NBOH-2C-B) is a derivative of the phenethylamine derived hallucinogen 2C-B which has been sold as a designer drug. It acts as a potent serotonin receptor agonist with similar affinity to the better-known compound 25B-NBOMe at 5-HT2A and 5-HT2C receptors with Dissociation constant values of 8.3 and 9.4, respectively.[2][3][4][5][6][7]

Society and culture

Canada

25B-NBOH is a controlled substance in Canada under phenethylamine blanket-ban language.[8]

Sweden

The Riksdag added 25B-NBOH to Narcotic Drugs Punishments Act under Swedish Schedule I ("substances, plant materials and fungi which normally do not have medical use") as of January 26, 2016, published by Medical Products Agency (MPA) in regulation HSLF-FS 2015:35 listed as 25B-NBOH, and 2-([2-(4-bromo-2,5-dimetoxifenyl)etylamino]metyl)fenol.[9]

United States

25B-NBOH is not an explicitly controlled substance in the United States.[10] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União. Archived 2023-08-27 at the Wayback Machine. Retrieved 2023-08-27.
  2. ^ Heim, Ralf (19 March 2004). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur (Ph.D.). Freie Universität Berlin. Archived 16 April 2012 at the Wayback Machine. Retrieved 27 June 2015.
  3. ^ Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (March 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
  4. ^ Hansen M (2010-12-16). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. (Ph.D.). University of Copenhagen. doi:10.13140/RG.2.2.33671.14245
  5. ^ Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, Kristensen J, Begtrup M, Knudsen GM (April 2011). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–93. doi:10.1007/s00259-010-1686-8. PMID 21174090. S2CID 12467684
  6. ^ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A 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. S2CID 3103050
  7. ^ Braden MR, Parrish JC, Naylor JC, Nichols DE (December 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): 1956–64. doi:10.1124/mol.106.028720. PMID 17000863. S2CID 15840304
  8. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  9. ^ "Läkemedelsverkets föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotik" [The Swedish Medicines Agency's regulations on amendments to the Swedish Medicines Agency's regulations (LVFS 2011: 10) on lists of drugs]. Läkemedelsverket. Archived from the original on 2017-10-31. Retrieved 2017-04-21.
  10. ^ "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)", United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026