Warning: file_put_contents(/opt/frankenphp/design.onmedianet.com/storage/proxy/cache/c551b074e50e1eed9181972a63d7c8ca.html): Failed to open stream: No space left on device in /opt/frankenphp/design.onmedianet.com/app/src/Arsae/CacheManager.php on line 36

Warning: http_response_code(): Cannot set response code - headers already sent (output started at /opt/frankenphp/design.onmedianet.com/app/src/Arsae/CacheManager.php:36) in /opt/frankenphp/design.onmedianet.com/app/src/Models/Response.php on line 17

Warning: Cannot modify header information - headers already sent by (output started at /opt/frankenphp/design.onmedianet.com/app/src/Arsae/CacheManager.php:36) in /opt/frankenphp/design.onmedianet.com/app/src/Models/Response.php on line 20
Extensive Rigid Analogue Design Maps the Binding Conformation of Potent N-Benzylphenethylamine 5-HT2A Serotonin Receptor Agonist Ligands | ACS Chemical Neuroscience
ACS Publications. Most Trusted. Most Cited. Most Read
Extensive Rigid Analogue Design Maps the Binding Conformation of Potent N-Benzylphenethylamine 5-HT2A Serotonin Receptor Agonist Ligands
Advanced Search
    Research Article

    Extensive Rigid Analogue Design Maps the Binding Conformation of Potent N-Benzylphenethylamine 5-HT2A Serotonin Receptor Agonist Ligands
    Click to copy article linkArticle link copied!

    View Author Information
    Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University, West Lafayette, Indiana 47907, United States
    *Mailing address: Dept. of Medicinal Chemistry and Molecular Pharmacology RHPH Pharmacy Building, Rm 506C, 575 Stadium Mall Drive, Purdue University, West Lafayette, IN 47907-2091. Telephone: (765) 494-1461. Fax: (765) 494-1414. E-mail: [email protected]
    Other Access OptionsSupporting Information (2)

    ACS Chemical Neuroscience

    Cite this: ACS Chem. Neurosci. 2013, 4, 1, 96–109
    Click to copy citationCitation copied!
    https://doi.org/10.1021/cn3000668
    Published July 17, 2012
    Copyright © 2012 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Based on the structure of the superpotent 5-HT2A agonist 2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine, which consists of a ring-substituted phenethylamine skeleton modified with an N-benzyl group, we designed and synthesized a small library of constrained analogues to identify the optimal arrangement of the pharmacophoric elements of the ligand. Structures consisted of diversely substituted tetrahydroisoquinolines, piperidines, and one benzazepine. Based on the structure of (S,S)-9b, which showed the highest affinity of the series, we propose an optimal binding conformation. (S,S)-9b also displayed 124-fold selectivity for the 5-HT2A over the 5-HT2C receptor, making it the most selective 5-HT2A receptor agonist ligand currently known.

    Copyright © 2012 American Chemical Society

    Subjects

    what are subjects

    Keywords

    what are keywords

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    Details on the creation and refinement of homology models of the 5-HT2A receptor and the X-ray crystal structure of 36a in pdb format. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 50 publications.

    1. Tyler G. Fenske, John L. McKee, Natalie G. Cavalco, Serena S. Schalk, Emma M. Bonniwell, Josie C. Lammers, Naomi Shacham, Bruna Cuccurazzu, Adam L. Halberstadt, John D. McCorvy. Discovery of Highly Selective 5-HT2A Agonists Using Structure-Guided Design. Journal of Medicinal Chemistry 2025, 68 (19) , 20619-20635. https://doi.org/10.1021/acs.jmedchem.5c01855
    2. Alexandra Sink, Eline Pottie, Samuel J. Carter, Robert J. Tombari, Verena Weber, Paolo Carloni, Giulia Rossetti, David E. Olson, Christophe P. Stove, Michael Decker. Design, Synthesis, and In Vitro Characterization of a Tryptamine-Based Visible-Light Photoswitchable 5-HT2AR Ligand Showing Efficacy Preference for β-Arrestin over Mini-Gq. Journal of Medicinal Chemistry 2025, 68 (13) , 13628-13639. https://doi.org/10.1021/acs.jmedchem.5c00442
    3. Nikita P. Ilyin, Arslan D. Nabiullin, Anna D. Kozlova, Olga V. Kupriyanova, Vadim A. Shevyrin, Tatyana Gloriozova, Dmitry Filimonov, Alexey Lagunin, David S. Galstyan, Tatiana O. Kolesnikova, Mikael S. Mor, Evgeniya V. Efimova, Vladimir Poroikov, Konstantin B. Yenkoyan, Murilo S. de Abreu, Konstantin A. Demin, Allan V. Kalueff. Chronic Behavioral and Neurochemical Effects of Four Novel N-Benzyl-2-phenylethylamine Derivatives Recently Identified as “Psychoactive” in Adult Zebrafish Screens. ACS Chemical Neuroscience 2024, 15 (10) , 2006-2017. https://doi.org/10.1021/acschemneuro.4c00017
    4. Emil M. Ro̷rsted, Anders A. Jensen, Gints Smits, Karla Frydenvang, Jesper L. Kristensen. Discovery and Structure–Activity Relationships of 2,5-Dimethoxyphenylpiperidines as Selective Serotonin 5-HT2A Receptor Agonists. Journal of Medicinal Chemistry 2024, 67 (9) , 7224-7244. https://doi.org/10.1021/acs.jmedchem.4c00082
    5. Navoda Jayakodiarachchi, Mallory A. Maurer, Daniel C. Schultz, Cayden J. Dodd, Analisa Thompson Gray, Hyekyung P. Cho, Olivier Boutaud, Carrie K. Jones, Craig W. Lindsley, Aaron M. Bender. Evaluation of the Indazole Analogs of 5-MeO-DMT and Related Tryptamines as Serotonin Receptor 2 Agonists. ACS Medicinal Chemistry Letters 2024, 15 (2) , 302-309. https://doi.org/10.1021/acsmedchemlett.3c00566
    6. Wenwen Duan, Dongmei Cao, Sheng Wang, Jianjun Cheng. Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants. Chemical Reviews 2024, 124 (1) , 124-163. https://doi.org/10.1021/acs.chemrev.3c00375
    7. Andrew A. BolingerNoelle C. AnastasioKathryn A. CunninghamJia Zhou. THE SEROTONIN 5-HT2A RECEPTOR AS AN EVOLVING NEUROTHERAPEUTIC TARGET. , 53-81. https://doi.org/10.1021/mc-2023-vol58.ch03
    8. Emil Marcher-Rørsted, Jitka Nykodemová, Kasper Harpsøe, Anders A. Jensen, Jesper L. Kristensen. Introducing Conformational Restraints on 25CN-NBOH: A Selective 5-HT2A Receptor Agonist. ACS Medicinal Chemistry Letters 2023, 14 (3) , 319-325. https://doi.org/10.1021/acsmedchemlett.3c00014
    9. Christian B. M. Poulie, Eline Pottie, Icaro A. Simon, Kasper Harpsøe, Laura D’Andrea, Igor V. Komarov, David E. Gloriam, Anders A. Jensen, Christophe P. Stove, Jesper L. Kristensen. Discovery of β-Arrestin-Biased 25CN-NBOH-Derived 5-HT2A Receptor Agonists. Journal of Medicinal Chemistry 2022, 65 (18) , 12031-12043. https://doi.org/10.1021/acs.jmedchem.2c00702
    10. Konstantin A. Demin, Olga V. Kupriyanova, Vadim A. Shevyrin, Ksenia A. Derzhavina, Nataliya A. Krotova, Nikita P. Ilyin, Tatiana O. Kolesnikova, David S. Galstyan, Yurii M. Kositsyn, Abubakar-Askhab S. Khaybaev, Maria V. Seredinskaya, Yaroslav Dubrovskii, Raziya G. Sadykova, Maria O. Nerush, Mikael S. Mor, Elena V. Petersen, Tatyana Strekalova, Evgeniya V. Efimova, Savelii R. Kuvarzin, Konstantin B. Yenkoyan, Dmitrii V. Bozhko, Vladislav O. Myrov, Sofia M. Kolchanova, Aleksander I. Polovian, Georgii K. Galumov, Allan V. Kalueff. Acute behavioral and Neurochemical Effects of Novel N-Benzyl-2-Phenylethylamine Derivatives in Adult Zebrafish. ACS Chemical Neuroscience 2022, 13 (13) , 1902-1922. https://doi.org/10.1021/acschemneuro.2c00123
    11. Matthias Schmid, Kevin R. Sokol, Lukas A. Wein, Sofia Torres Venegas, Christina Meisenbichler, Klaus Wurst, Maren Podewitz, Thomas Magauer. Synthesis of Vicinal Quaternary All-Carbon Centers via Acid-catalyzed Cycloisomerization of Neopentylic Epoxides. Organic Letters 2020, 22 (16) , 6526-6531. https://doi.org/10.1021/acs.orglett.0c02296
    12. Emil Marcher-Rørsted, Adam L. Halberstadt, Adam K. Klein, Muhammad Chatha, Simon Jademyr, Anders A. Jensen, Jesper L. Kristensen. Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists. ACS Chemical Neuroscience 2020, 11 (9) , 1238-1244. https://doi.org/10.1021/acschemneuro.0c00129
    13. Pei-Chao Zhang, Yidong Wang, Zhan-Ming Zhang, Junliang Zhang. Gold(I)/Xiang-Phos-Catalyzed Asymmetric Intramolecular Cyclopropanation of Indenes and Trisubstituted Alkenes. Organic Letters 2018, 20 (22) , 7049-7052. https://doi.org/10.1021/acs.orglett.8b02999
    14. Michael J. Houghton and David B. Collum . Lithium Enolates Derived from Weinreb Amides: Insights into Five-Membered Chelate Rings. The Journal of Organic Chemistry 2016, 81 (22) , 11057-11064. https://doi.org/10.1021/acs.joc.6b02067
    15. Sebastian Leth-Petersen, Charlotte Gabel-Jensen, Nic Gillings, Szabolzs Lehel, Hanne D. Hansen, Gitte M. Knudsen, and Jesper L. Kristensen . Metabolic Fate of Hallucinogenic NBOMes. Chemical Research in Toxicology 2016, 29 (1) , 96-100. https://doi.org/10.1021/acs.chemrestox.5b00450
    16. David E. Nichols, M. Flori Sassano, Adam L. Halberstadt, Landon M. Klein, Simon D. Brandt, Simon P. Elliott, and Wolfgang J. Fiedler . N-Benzyl-5-methoxytryptamines as Potent Serotonin 5-HT2 Receptor Family Agonists and Comparison with a Series of Phenethylamine Analogues. ACS Chemical Neuroscience 2015, 6 (7) , 1165-1175. https://doi.org/10.1021/cn500292d
    17. Martin Hansen, Karina Phonekeo, James S. Paine, Sebastian Leth-Petersen, Mikael Begtrup, Hans Bräuner-Osborne, and Jesper L. Kristensen . Synthesis and Structure–Activity Relationships of N-Benzyl Phenethylamines as 5-HT2A/2C Agonists. ACS Chemical Neuroscience 2014, 5 (3) , 243-249. https://doi.org/10.1021/cn400216u
    18. Anne M. Andrews (Associate Editor). Celebrating Serotonin. ACS Chemical Neuroscience 2012, 3 (9) , 644-645. https://doi.org/10.1021/cn300137q
    19. Lei Zhu, Jun Huang. Total Synthesis of Lugdunomycin via Sequential Photoinduced Spiroketalization and Isobenzofuran Diels–Alder Reactions. Angewandte Chemie 2025, 137 (22) https://doi.org/10.1002/ange.202422615
    20. Lei Zhu, Jun Huang. Total Synthesis of Lugdunomycin via Sequential Photoinduced Spiroketalization and Isobenzofuran Diels–Alder Reactions. Angewandte Chemie International Edition 2025, 64 (22) https://doi.org/10.1002/anie.202422615
    21. Yiming Hu, Jiayu Xu, Min Tang, Yawen Liu, Liping Guan, Qinghao Jin. Design, Synthesis and Biological Activity Studies of 2-(1,3-Dioxoiso-indolin-2-yl)-N-phenethylacetamide and 2-(3,4-Dihydroisoquinolin-1-yl)isoindole-1,3-dione as Monoamine Oxidase (MAO) and Cholinesterase (ChE) Inhibitors. Chinese Journal of Organic Chemistry 2024, 44 (6) , 1907. https://doi.org/10.6023/cjoc202311027
    22. Jason Wallach, Andrew B. Cao, Maggie M. Calkins, Andrew J. Heim, Janelle K. Lanham, Emma M. Bonniwell, Joseph J. Hennessey, Hailey A. Bock, Emilie I. Anderson, Alexander M. Sherwood, Hamilton Morris, Robbin de Klein, Adam K. Klein, Bruna Cuccurazzu, James Gamrat, Tilka Fannana, Randy Zauhar, Adam L. Halberstadt, John D. McCorvy. Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential. Nature Communications 2023, 14 (1) https://doi.org/10.1038/s41467-023-44016-1
    23. Eline Pottie, Christophe P. Stove. In vitro assays for the functional characterization of (psychedelic) substances at the serotonin receptor 5‐HT 2A R. Journal of Neurochemistry 2022, 162 (1) , 39-59. https://doi.org/10.1111/jnc.15570
    24. Karolina E. Kolaczynska, Dino Luethi, Daniel Trachsel, Marius C. Hoener, Matthias E. Liechti. Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines. Frontiers in Pharmacology 2022, 12 https://doi.org/10.3389/fphar.2021.794254
    25. Xinhui Yu, Ting Zhang, Jitian Liu, Xiaoxun Li. Recent Advances in the Construction of Quaternary Stereocenters via Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation. Synthesis 2021, 53 (23) , 4341-4352. https://doi.org/10.1055/a-1533-3085
    26. Emil Märcher Rørsted, Anders A. Jensen, Jesper L. Kristensen. 25CN‐NBOH: A Selective Agonist for in vitro and in vivo Investigations of the Serotonin 2A Receptor. ChemMedChem 2021, 16 (21) , 3263-3270. https://doi.org/10.1002/cmdc.202100395
    27. Wellington Alves de Barros, Marcelo Pereira Queiroz, Leonardo da Silva Neto, Graziele Martins Borges, Felipe Terra Martins, Ângelo de Fátima. Synthesis of 25X-BOMes and 25X-NBOHs (X = H, I, Br) for pharmacological studies and as reference standards for forensic purposes. Tetrahedron Letters 2021, 66 , 152804. https://doi.org/10.1016/j.tetlet.2020.152804
    28. Katarzyna Kamińska, Paweł Świt, Kamilla Malek. 2-(4-Iodo-2,5-dimethoxyphenyl)- N -[(2-methoxyphenyl)methyl]ethanamine (25I-NBOME): A Harmful Hallucinogen Review. Journal of Analytical Toxicology 2021, 44 (9) , 947-956. https://doi.org/10.1093/jat/bkaa022
    29. Nicholas M. Barnes, Gerard P. Ahern, Carine Becamel, Joël Bockaert, Michael Camilleri, Severine Chaumont-Dubel, Sylvie Claeysen, Kathryn A. Cunningham, Kevin C. Fone, Michael Gershon, Giuseppe Di Giovanni, Nathalie M. Goodfellow, Adam L. Halberstadt, Rachel M. Hartley, Ghérici Hassaine, Katharine Herrick-Davis, Ruud Hovius, Enza Lacivita, Evelyn K. Lambe, Marcello Leopoldo, Finn Olav Levy, Sarah C.R. Lummis, Philippe Marin, Luc Maroteaux, Andrew C. McCreary, David L. Nelson, John F. Neumaier, Adrian Newman-Tancredi, Hugues Nury, Alexander Roberts, Bryan L. Roth, Anne Roumier, Gareth J. Sanger, Milt Teitler, Trevor Sharp, Carlos M. Villalón, Horst Vogel, Stephanie W. Watts, Daniel Hoyer. International Union of Basic and Clinical Pharmacology. CX. Classification of Receptors for 5-hydroxytryptamine; Pharmacology and Function. Pharmacological Reviews 2021, 73 (1) , 310-520. https://doi.org/10.1124/pr.118.015552
    30. Anders A. Jensen, Adam L. Halberstadt, Emil Märcher-Rørsted, Anna U. Odland, Muhammad Chatha, Nikolaj Speth, Gudrun Liebscher, Martin Hansen, Hans Bräuner-Osborne, Mikael Palner, Jesper T. Andreasen, Jesper L. Kristensen. 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. https://doi.org/10.1016/j.bcp.2020.113979
    31. Adam L. Halberstadt, Muhammad Chatha, Adam K. Klein, Jason Wallach, Simon D. Brandt. Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species. Neuropharmacology 2020, 167 , 107933. https://doi.org/10.1016/j.neuropharm.2019.107933
    32. Jolanta B. Zawilska, Monika Kacela, Piotr Adamowicz. NBOMes–Highly Potent and Toxic Alternatives of LSD. Frontiers in Neuroscience 2020, 14 https://doi.org/10.3389/fnins.2020.00078
    33. Adam L. Halberstadt, Muhammad Chatha, Alexander Stratford, Matthias Grill, Simon D. Brandt. Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran (“FLY”) and benzodifuran (“DragonFLY”) analogs. Neuropharmacology 2019, 144 , 368-376. https://doi.org/10.1016/j.neuropharm.2018.10.037
    34. Giuseppe Di Giovanni, Philippe De Deurwaerdère. TCB-2 [(7R)-3-bromo-2, 5-dimethoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl]methanamine]: A hallucinogenic drug, a selective 5-HT2A receptor pharmacological tool, or none of the above?. Neuropharmacology 2018, 142 , 20-29. https://doi.org/10.1016/j.neuropharm.2017.10.004
    35. Mami Nakamura, Kaori Shintani-Ishida, Hiroshi Ikegaya. 5-HT2A Receptor Agonist-Induced Hyperthermia Is Induced via Vasoconstriction by Peripheral 5-HT2A Receptors and Brown Adipose Tissue Thermogenesis by Peripheral Serotonin Loss at a High Ambient Temperature. The Journal of Pharmacology and Experimental Therapeutics 2018, 367 (2) , 356-362. https://doi.org/10.1124/jpet.118.250217
    36. Jeong A Yoon, Sungwan Ahn, Young Taek Han. Synthesis of Ficusnotins, Rare 1,4-Diarylbutanoids Derived from Ficusnota , via Ruthenium-Catalyzed Conjugate Addition. Natural Product Communications 2018, 13 (3) https://doi.org/10.1177/1934578X1801300320
    37. Laura Hondebrink, Anne Zwartsen, Remco H.S. Westerink. Effect fingerprinting of new psychoactive substances (NPS): What can we learn from in vitro data?. Pharmacology & Therapeutics 2018, 182 , 193-224. https://doi.org/10.1016/j.pharmthera.2017.10.022
    38. Achim T. Caspar, Andreas B. Kollas, Hans H. Maurer, Markus R. Meyer. Development of a quantitative approach in blood plasma for low-dosed hallucinogens and opioids using LC-high resolution mass spectrometry. Talanta 2018, 176 , 635-645. https://doi.org/10.1016/j.talanta.2017.08.063
    39. Thomas P. Blackburn. Actions of Drugs on The Brain and CNS Disorders. 2017, 130-220. https://doi.org/10.1039/BK9781782621423-00130
    40. Michael B. Gatch, Sean B. Dolan, Michael J. Forster. Locomotor and discriminative stimulus effects of four novel hallucinogens in rodents. Behavioural Pharmacology 2017, 28 (5) , 375-385. https://doi.org/10.1097/FBP.0000000000000309
    41. Anders A. Jensen, John D. McCorvy, Sebastian Leth-Petersen, Christoffer Bundgaard, Gudrun Liebscher, Terry P. Kenakin, Hans Bräuner-Osborne, Jan Kehler, Jesper Langgaard Kristensen. 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 (3) , 441-453. https://doi.org/10.1124/jpet.117.239905
    42. Adam L. Halberstadt. Pharmacology and Toxicology of N-Benzylphenethylamine (“NBOMe”) Hallucinogens. 2017, 283-311. https://doi.org/10.1007/7854_2016_64
    43. David E. Nichols. Chemistry and Structure–Activity Relationships of Psychedelics. 2017, 1-43. https://doi.org/10.1007/7854_2017_475
    44. Rajwinder Kaur, Reshu Sanan, Rakesh Kumar Mahajan. Probing interactions of neurotransmitters with twin tailed anionic surfactant: A detailed physicochemical study. Journal of Colloid and Interface Science 2016, 469 , 38-46. https://doi.org/10.1016/j.jcis.2016.02.006
    45. Ken-ichi Yoshida, Kanju Saka, Kaori Shintani-Ishida, Hideyuki Maeda, Makoto Nakajima, Shu-ichi Hara, Masahide Ueno, Katsunori Sasaki, Hirotaro Iwase, Tetsuya Sakamoto. A case of fatal intoxication due to the new designer drug 25B-NBOMe. Forensic Toxicology 2015, 33 (2) , 396-401. https://doi.org/10.1007/s11419-015-0276-7
    46. Martin Hansen, Stine Engesgaard Jacobsen, Shane Plunkett, Gudrun Eckhard Liebscher, John D. McCorvy, Hans Bräuner-Osborne, Jesper Langgaard Kristensen. Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists. Bioorganic & Medicinal Chemistry 2015, 23 (14) , 3933-3937. https://doi.org/10.1016/j.bmc.2014.12.011
    47. William E. Fantegrossi, Bradley W. Gray, Jessica M. Bailey, Douglas A. Smith, Martin Hansen, Jesper L. Kristensen. Hallucinogen-like effects of 2-([2-(4-cyano-2,5-dimethoxyphenyl) ethylamino]methyl)phenol (25CN-NBOH), a novel N-benzylphenethylamine with 100-fold selectivity for 5-HT2A receptors, in mice. Psychopharmacology 2015, 232 (6) , 1039-1047. https://doi.org/10.1007/s00213-014-3739-3
    48. Adam L. Halberstadt. Recent advances in the neuropsychopharmacology of serotonergic hallucinogens. Behavioural Brain Research 2015, 277 , 99-120. https://doi.org/10.1016/j.bbr.2014.07.016
    49. Rong Long, Jun Huang, Jianxian Gong, Zhen Yang. Direct construction of vicinal all-carbon quaternary stereocenters in natural product synthesis. Natural Product Reports 2015, 32 (11) , 1584-1601. https://doi.org/10.1039/C5NP00046G
    50. Sebastian Leth-Petersen, Christoffer Bundgaard, Martin Hansen, Martin A. Carnerup, Jan Kehler, Jesper Langgaard Kristensen. Correlating the Metabolic Stability of Psychedelic 5-HT2A Agonists with Anecdotal Reports of Human Oral Bioavailability. Neurochemical Research 2014, 39 (10) , 2018-2023. https://doi.org/10.1007/s11064-014-1253-y
    Go to
    Get e-Alerts
    Get e-Alerts

    ACS Chemical Neuroscience

    Cite this: ACS Chem. Neurosci. 2013, 4, 1, 96–109
    Click to copy citationCitation copied!
    https://doi.org/10.1021/cn3000668
    Published July 17, 2012
    Copyright © 2012 American Chemical Society
    Request reuse permissions

    Article Views

    2557

    Altmetric

    -

    Citations

    50
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.