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2C-B-3PIP-POMe

From Wikipedia, the free encyclopedia

Pharmaceutical compound
2C-B-3PIP-POMe
Clinical data
Drug classSerotonin receptor modulator;Serotonin5-HT2 receptoragonist;Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 5-(4-bromo-2,5-dimethoxyphenyl)-2-(2-methoxyphenyl)piperidine
PubChemCID
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 aserotonin receptor modulator of thephenethylamine,2C,3-phenylpiperidine (3PIP), andNBOMe families.[1][2][3][4] It is acyclized phenethylamine and along with2C-B-3PIP-NBOMe is an NBOMederivative of2C-B-3PIP.[1][2][3][4] The drug is a mixture ofcis- andtrans-isomers.[1][2][4] Its isomers show weakaffinity for theserotonin5-HT2A and5-HT2C receptors (Ki = 290–856 nM and 3,850–23,200 nM, respectively), with these affinities being profoundly reduced relative to those of2C-B.[1][2][4][5] Thecis isomer is a low-potencyagonist of the serotonin 5-HT2A receptor (EC50Tooltip half-maximal effective concentration = 480–2,300 nM;EmaxTooltip maximal efficacy = 87–94%), the serotonin5-HT2B receptor (EC50 = 770 nM;Emax = 20%), and the serotonin 5-HT2C receptor (EC50 = 170–2,000 nM;Emax = 80–82%), whereas thetrans isomer is inactive as an agonist of these receptors even at very high concentrations.[3] Thechemical synthesis of 2C-B-3PIP-POMe has been described.[1][2][3] 2C-B-3PIP-POMe was first described in thescientific literature by Martin Hansen in 2010.[1][2][3][4]

See also

[edit]

References

[edit]
  1. ^abcdefHansen 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. ^abcdefJuncosa 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. ^abcde"5-ht2a agonists for use in treatment of depression".Google Patents. 5 November 2020. Retrieved19 December 2025.
  4. ^abcdeTrachsel 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 fromthe 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.

External links

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