2C-B-3PIP

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2C-B-3PIP
Clinical data
Other names3-(4-Bromo-2,5-dimethoxyphenyl)piperidine; β,N-Trimethylene-2C-B
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 3-(4-bromo-2,5-dimethoxyphenyl)piperidine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC13H18BrNO2
Molar mass300.196 g·mol−1
3D model (JSmol)
  • COC1=CC(=C(C=C1C2CCCNC2)OC)Br
  • InChI=1S/C13H18BrNO2/c1-16-12-7-11(14)13(17-2)6-10(12)9-4-3-5-15-8-9/h6-7,9,15H,3-5,8H2,1-2H3
  • Key:ULJHXMHMDJQESG-UHFFFAOYSA-N

2C-B-3PIP, also known as 3-(4-bromo-2,5-dimethoxyphenyl)piperidine, is a serotonin receptor modulator of the phenethylamine, 2C, and 3-phenylpiperidine (3PIP) families related to the psychedelic drug LPH-5 ((S)-2C-TFM-3PIP).[1][2][3][4] It is a cyclized phenethylamine and is the derivative of 2C-B in which the β position has been connected to the amine to form a piperidine ring.[1][2][3][4]

Pharmacology

Pharmacodynamics

The drug is a racemic mixture of (R)- and (S)- enantiomers.[4] The eutomer or (S)- enantiomer is a serotonin 5-HT2A receptor partial agonist with an EC50Tooltip half-maximal effective concentration of 69 nM and an EmaxTooltip maximal efficacy of 37%, whereas this enantiomer was inactive as an agonist of the serotonin 5-HT2C receptor (EC50 = >50,000 nM) and instead showed low-potency antagonism at this receptor with an IC50Tooltip half-maximal inhibitory concentration of 640 nM.[4] The distomer or (R)- enantiomer is a serotonin 5-HT2A receptor partial agonist with an EC50 of 370 nM and Emax of 67% as well as a serotonin 5-HT2C receptor partial agonist with an EC50 of 1,900 nM and Emax of 34%.[4] The enantiomers are both dramatically less potent as serotonin 5-HT2A and 5-HT2C receptor agonists than 2C-B, which had an EC50 (Emax) of 1.6 nM (68%) at the serotonin 5-HT2A receptor and an EC50 (Emax) of 4.1 nM (74%) at the serotonin 5-HT2C receptor.[4] 2C-B-3PIP and its enantiomers were not assessed in animal behavioral studies and it is unknown whether they produce psychedelic-type effects.[3][4]

Chemistry

The chemical synthesis of 2C-B-3PIP has been described.[1][2][4] Derivatives of 2C-B-3PIP include the NBOMe-like 2C-B-3PIP-NBOMe and 2C-B-3PIP-POMe.[1][2][5] Some notable analogues of 2C-B-3PIP include 2C-B, LPH-5 ((S)-2C-TFM-3PIP), 2C-B-PYR, ZC-B (2C-B-AZET), 2C-B-morpholine (2C-B-MOR), 2C-B-aminorex (2C-B-AR), 2C-B-PP, and DMBMPP, among others.[4][5][1]

History

2C-B-3PIP was first described in the scientific literature by Martin Hansen in 2010.[1] Its pharmacology was subsequently described by Emil Märcher-Rørsted and colleagues in association with Lophora in the 2020s.[3][4] The closely related drug LPH-5, which is a selective serotonin 5-HT2A receptor agonist and psychedelic drug, is under development by Lophora for the treatment of major depressive disorder.[6][4][7][8][9]

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. 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.
  5. 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. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 13 November 2025. Retrieved 19 December 2025.
  6. Cameron LP, Jaster AM, Ramos R, Ullman EZ (2025). "The Utility of DOI For the Study of Serotonin 2A and 2C Receptors". Molecular Pharmacology. 108 (1) 100093. doi:10.1016/j.molpha.2025.100093. PMID 41447818.
  7. Jensen AA, Cecchi CR, Hibicke M, Bach AH, Kaadt E, Märcher-Rørsted E, et al. (June 2025). "The Selective Serotonin 5‑HT2A Receptor Agonist (S)‑3-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)piperidine (LPH-5) Induces Persistent and Robust Antidepressant-Like Effects in Rodents". ACS Pharmacology & Translational Science. 8 (6): 1791–1803. doi:10.1021/acsptsci.5c00208. PMC 12171885. PMID 40534669.
  8. "LPH 5". AdisInsight. 11 November 2025. Retrieved 19 December 2025.
  9. "Delving into the Latest Updates on LPH-5 with Synapse". Synapse. 15 November 2025. Retrieved 19 December 2025.