2C-B-3PIP-NBOMe

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2C-B-3PIP-NBOMe
Clinical data
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 3-(4-bromo-2,5-dimethoxyphenyl)-1-[(2-methoxyphenyl)methyl]piperidine
Chemical and physical data
FormulaC21H26BrNO3
Molar mass420.347 g·mol−1
3D model (JSmol)
  • COc1cc(Br)c(cc1C1CCCN(C1)Cc1ccccc1OC)OC
  • InChI=1S/C21H26BrNO3/c1-24-19-9-5-4-7-16(19)14-23-10-6-8-15(13-23)17-11-21(26-3)18(22)12-20(17)25-2/h4-5,7,9,11-12,15H,6,8,10,13-14H2,1-3H3
  • Key:XCBPFHGQWYIAJG-UHFFFAOYSA-N

2C-B-3PIP-NBOMe is a serotonin receptor modulator of the phenethylamine, 2C, 3-phenylpiperidine (3PIP), and NBOMe families.[1][2][3] It is a cyclized phenethylamine and along with 2C-B-3PIP-POMe is an NBOMe derivative of 2C-B-3PIP.[1][2][3] The drug shows very weak affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 2,150 nM and 5,880 nM, respectively), with its affinities being profoundly reduced relative to those of 2C-B.[1][2][3][4] The chemical synthesis of 2C-B-3PIP-NBOMe has been described.[1][2] 2C-B-3PIP-NBOMe was first described in the scientific literature by Martin Hansen in 2010.[1][2][3]

See also

References

  1. Hansen M (2010-12-16). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (Ph.D. thesis). University of Copenhagen. doi:10.13140/RG.2.2.33671.14245.
  2. Juncosa JI, Hansen M, Bonner LA, Cueva JP, Maglathlin R, McCorvy JD, et al. (January 2013). "Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands". ACS Chemical Neuroscience. 4 (1): 96–109. doi:10.1021/cn3000668. PMC 3547484. PMID 23336049.
  3. Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. p. 867. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  4. M Ro Rsted E, Jensen AA, Smits G, Frydenvang K, Kristensen JL (May 2024). "Discovery and Structure-Activity Relationships of 2,5-Dimethoxyphenylpiperidines as Selective Serotonin 5-HT2A Receptor Agonists". Journal of Medicinal Chemistry. 67 (9): 7224–7244. doi:10.1021/acs.jmedchem.4c00082. PMC 11089506. PMID 38648420.