25B-NBOH

25B-NBOH

Systematic (IUPAC) name
2-((4-bromo-2,5-dimethoxyphenethylamino)methyl)phenol
Clinical data
Legal status
Legal status	UK: Class A
Identifiers
CAS Number	1335331-46-8
Chemical data
Formula	C17H20BrNO3
Molar mass	365.06 g/mol
SMILES BrC2=CC(=C(CCNCC1=C(C=CC=C1)O)C=C2OC)OC
InChI InChI=1S/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 Key:RSUNJYKZRKIBNB-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-HT_2A and 5-HT_2C receptors with pK_is values of 8.3 and 9.4, respectively.^{[1][2][3][4][5][6]}

Legal status

25B-NBOH is illegal in Sweden as of 26. January 2016.^[7]

See also

• 25C-NBOH
• 25I-NBOH
• 25CN-NBOH
• 2CBCB-NBOMe
• 2CBFly-NBOMe
• 25B-NBOMe
• 25C-NBOMe
• 25I-NBMD
• 25I-NBOMe
• 25TFM-NBOMe
• 25I-NBF

References

1. Heim, Ralf (19 March 2004). "Synthese und Pharmakologie potenter 5-HT_2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur". Freie Unversität Berlin. Retrieved 27 June 2015.
2. 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-HT_2A/2C Agonists". ACS Chemical Neuroscience 5 (3): 243–9. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.
3. Martin Hansen (2011). "Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain." (PDF). University of Copenhagen. Retrieved 27 June 2015.
4. 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-HT_2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging 38 (4): 681–693. doi:10.1007/s00259-010-1686-8. PMID 21174090.
5. 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. doi:10.1007/s10822-010-9400-2. PMID 21088982.
6. 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.
7. "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.