2C-B-3PIP

Last updated

2C-B-3PIP
2C-B-3PIP.svg
Clinical data
Other names3-(4-Bromo-2,5-dimethoxyphenyl)piperidine; β,N-Trimethylene-2C-B
Drug class Serotonin 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
Formula C13H18BrNO2
Molar mass 300.196 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]

Contents

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 EC50 Tooltip half-maximal effective concentration of 69 nM and an Emax Tooltip 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 IC50 Tooltip 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. 1 2 3 4 5 6 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. 1 2 3 4 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. 1 2 3 4 "5-ht2a agonists for use in treatment of depression". Google Patents. 5 November 2020. Retrieved 19 December 2025.
  4. 1 2 3 4 5 6 7 8 9 10 11 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. 1 2 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 21 August 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 100093. doi:10.1016/j.molpha.2025.100093.
  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. 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.
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