trans-2-(2,5-Dimethoxy-4-iodophenyl)cyclopropylamine and trans-2-(2,5-dimethoxy-4-bromophenyl)cyclopropylamine as potent agonists for the 5-HT2 receptor family

Adam Pigott, Stewart Frescas, John D. McCorvy, Xi-Ping Huang, Bryan L. Roth and David E. Nichols
Beilstein J. Org. Chem. 2012, 8, 1705–1709. https://doi.org/10.3762/bjoc.8.194

Supporting Information

Supporting Information File 1: Experimental details for all new compounds as well as the pharmacological methods used to measure receptor affinity and functional activity.
Format: PDF Size: 206.7 KB Download

Cite the Following Article

trans-2-(2,5-Dimethoxy-4-iodophenyl)cyclopropylamine and trans-2-(2,5-dimethoxy-4-bromophenyl)cyclopropylamine as potent agonists for the 5-HT2 receptor family
Adam Pigott, Stewart Frescas, John D. McCorvy, Xi-Ping Huang, Bryan L. Roth and David E. Nichols
Beilstein J. Org. Chem. 2012, 8, 1705–1709. https://doi.org/10.3762/bjoc.8.194

How to Cite

Pigott, A.; Frescas, S.; McCorvy, J. D.; Huang, X.-P.; Roth, B. L.; Nichols, D. E. Beilstein J. Org. Chem. 2012, 8, 1705–1709. doi:10.3762/bjoc.8.194

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Duan, W.; Cao, D.; Wang, S.; Cheng, J. Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants. Chemical reviews 2023, 124, 124–163. doi:10.1021/acs.chemrev.3c00375
  • Odland, A. U.; Kristensen, J. L.; Andreasen, J. T. Animal Behavior in Psychedelic Research. Pharmacological reviews 2022, 74, 1176–1205. doi:10.1124/pharmrev.122.000590
  • Pottie, E.; Stove, C. P. In vitro assays for the functional characterization of (psychedelic) substances at the serotonin receptor 5-HT2A R. Journal of neurochemistry 2022, 162, 39–59. doi:10.1111/jnc.15570
  • Rørsted, E. M.; Jensen, A. A.; Kristensen, J. L. 25CN-NBOH: A Selective Agonist for in vitro and in vivo Investigations of the Serotonin 2A Receptor. ChemMedChem 2021, 16, 3263–3270. doi:10.1002/cmdc.202100395
  • Menchikov, L. G.; Shulishov, E. V.; Tomilov, Y. V. Recent advances in the catalytic cyclopropanation of unsaturated compounds with diazomethane. Russian Chemical Reviews 2021, 90, 199–230. doi:10.1070/rcr4982
  • Jensen, A. A.; Halberstadt, A. L.; Märcher-Rørsted, E.; Odland, A. U.; Chatha, M.; Speth, N.; Liebscher, G.; Hansen, M.; Bräuner-Osborne, H.; Palner, M.; Andreasen, J. T.; Kristensen, J. L. The selective 5-HT2A receptor agonist 25CN-NBOH: structure-activity relationship, in vivo pharmacology, and in vitro and ex vivo binding characteristics of [3H]25CN-NBOH. Biochemical pharmacology 2020, 177, 113979. doi:10.1016/j.bcp.2020.113979
  • Poulie, C. B. M.; Jensen, A. A.; Halberstadt, A. L.; Kristensen, J. L. DARK Classics in Chemical Neuroscience: NBOMes. ACS chemical neuroscience 2019, 11, 3860–3869. doi:10.1021/acschemneuro.9b00528
  • Diez-Alarcia, R.; Yáñez-Pérez, V.; Muneta-Arrate, I.; Arrasate, S.; Lete, E.; Meana, J. J.; González-Díaz, H. Big Data Challenges Targeting Proteins in GPCR Signaling Pathways; Combining PTML-ChEMBL Models and [35S]GTPγS Binding Assays. ACS chemical neuroscience 2019, 10, 4476–4491. doi:10.1021/acschemneuro.9b00302
  • Saber, I.; Milewski, A.; Reitz, A. B.; Rawls, S. M.; Walker, E. A. Effects of dopaminergic and serotonergic compounds in rats trained to discriminate a high and a low training dose of the synthetic cathinone mephedrone. Psychopharmacology 2019, 236, 1015–1029. doi:10.1007/s00213-019-05241-z
  • Nichols, D. E. Chemistry and Structure–Activity Relationships of Psychedelics. Current topics in behavioral neurosciences 2018, 36, 1–43. doi:10.1007/7854_2017_475
  • Jensen, A. A.; McCorvy, J. D.; Leth-Petersen, S.; Bundgaard, C.; Liebscher, G.; Kenakin, T. P.; Bräuner-Osborne, H.; Kehler, J.; Kristensen, J. L. Detailed Characterization of the In Vitro Pharmacological and Pharmacokinetic Properties of N-(2-Hydroxybenzyl)-2, 5-Dimethoxy-4-Cyanophenylethylamine (25CN-NBOH), a Highly Selective and Brain-Penetrant 5-HT2A Receptor Agonist. The Journal of pharmacology and experimental therapeutics 2017, 361, 441–453. doi:10.1124/jpet.117.239905
  • Prabhakaran, J.; Sai, K. K. S.; Zanderigo, F.; Rubin-Falcone, H.; Jorgensen, M. J.; Kaplan, J. R.; Tooke, K. I.; Mintz, A.; Mann, J. J.; Kumar, J. S. D. In vivo evaluation of [18F]FECIMBI-36, an agonist 5-HT2A/2C receptor PET radioligand in nonhuman primate. Bioorganic & medicinal chemistry letters 2016, 27, 21–23. doi:10.1016/j.bmcl.2016.11.043
  • Halberstadt, A. L.; Sindhunata, I. S.; Scheffers, K.; Flynn, A. D.; Sharp, R. F.; Geyer, M. A.; Young, J. W. Effect of 5-HT2A and 5-HT2C receptors on temporal discrimination by mice. Neuropharmacology 2016, 107, 364–375. doi:10.1016/j.neuropharm.2016.03.038
  • Wang, H.; Zhou, X.; Mao, Y. ASYMMETRIC SYNTHESIS OF CYCLOPROPYLAMINE DERIVATIVES. HETEROCYCLES 2014, 89, 1767–1800. doi:10.3987/rev-14-796
Other Beilstein-Institut Open Science Activities