2C-B-3PIP-POMe

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2C-B-3PIP-POMe
Clinical data
Drug classSerotonin receptor modulator; Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 5-(4-bromo-2,5-dimethoxyphenyl)-2-(2-methoxyphenyl)piperidine
PubChem CID
Chemical and physical data
FormulaC20H24BrNO3
Molar mass406.320 g·mol−1
3D model (JSmol)
  • COC1=CC=CC=C1C2CCC(CN2)C3=CC(=C(C=C3OC)Br)OC
  • InChI=1S/C20H24BrNO3/c1-23-18-7-5-4-6-14(18)17-9-8-13(12-22-17)15-10-20(25-3)16(21)11-19(15)24-2/h4-7,10-11,13,17,22H,8-9,12H2,1-3H3
  • Key:BDZXVOHNVCEDNQ-UHFFFAOYSA-N

2C-B-3PIP-POMe is a serotonin receptor modulator of the phenethylamine, 2C, 3-phenylpiperidine (3PIP), and NBOMe families.[1][2][3][4] It is a cyclized phenethylamine and along with 2C-B-3PIP-NBOMe is an NBOMe derivative of 2C-B-3PIP.[1][2][3][4] The drug is a mixture of cis- and trans- isomers.[1][2][4] Its isomers show weak affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 290–856 nM and 3,850–23,200 nM, respectively), with these affinities being profoundly reduced relative to those of 2C-B.[1][2][4][5] The cis isomer is a low-potency agonist of the serotonin 5-HT2A receptor (EC50Tooltip half-maximal effective concentration = 480–2,300 nM; EmaxTooltip maximal efficacy = 87–94%), the serotonin 5-HT2B receptor (EC50 = 770 nM; Emax = 20%), and the serotonin 5-HT2C receptor (EC50 = 170–2,000 nM; Emax = 80–82%), whereas the trans isomer is inactive as an agonist of these receptors even at very high concentrations.[3] The chemical synthesis of 2C-B-3PIP-POMe has been described.[1][2][3] 2C-B-3PIP-POMe was first described in the scientific literature by Martin Hansen in 2010.[1][2][3][4]

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. "5-ht2a agonists for use in treatment of depression". Google Patents. 5 November 2020. Retrieved 19 December 2025.
  4. 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.
  5. 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.