Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect
ACS Publications. Most Trusted. Most Cited. Most Read
Isolation, Structure, and Partial Synthesis of an Active Constituent of Hashish
My Activity

Figure 1Loading Img
    Article

    Isolation, Structure, and Partial Synthesis of an Active Constituent of Hashish
    Click to copy article linkArticle link copied!

    ACS Legacy Archive
    Other Access Options

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 1964, 86, 8, 1646–1647
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja01062a046
    Published April 1, 1964

    Note: In lieu of an abstract, this is the article's first page.

    Free first page

    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.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 1762 publications.

    1. Glen P. Jackson, Mark A. Barkett. Forensic Mass Spectrometry: Scientific and Legal Precedents. Journal of the American Society for Mass Spectrometry 2023, 34 (7) , 1210-1224. https://doi.org/10.1021/jasms.3c00124
    2. Yarden Lavi, Natalya M. Kogan, Louise M. Topping, Caojie Liu, Fiona E. McCann, Richard O. Williams, Aviva Breuer, Zhanna Yekhtin, Aviva Friedman Ezra, Ruth Gallily, Marc Feldmann, Raphael Mechoulam. Novel Synthesis of C-Methylated Phytocannabinoids Bearing Anti-inflammatory Properties. Journal of Medicinal Chemistry 2023, 66 (8) , 5536-5549. https://doi.org/10.1021/acs.jmedchem.2c01988
    3. Hayley M. Green, David B. Finlay, Ruth A. Ross, Iain R. Greig, Stephen B. Duffull, Michelle Glass. In Vitro Characterization of 6-Methyl-3-(2-nitro-1-(thiophen-2-yl)ethyl)-2-phenyl-1H-indole (ZCZ011) at the Type 1 Cannabinoid Receptor: Allosteric Agonist or Allosteric Modulator?. ACS Pharmacology & Translational Science 2022, 5 (12) , 1279-1291. https://doi.org/10.1021/acsptsci.2c00160
    4. Diego A. Rodríguez-Soacha, Sophie A. M. Steinmüller, Ali Işbilir, Julia Fender, Marie H. Deventer, Yesid A. Ramírez, Anna Tutov, Christoph Sotriffer, Christophe P. Stove, Kristina Lorenz, Martin J. Lohse, James N. Hislop, Michael Decker. Development of an Indole-Amide-Based Photoswitchable Cannabinoid Receptor Subtype 1 (CB1R) “Cis-On” Agonist. ACS Chemical Neuroscience 2022, 13 (16) , 2410-2435. https://doi.org/10.1021/acschemneuro.2c00160
    5. Gia-Nam Nguyen, Erin Noel Jordan, Oliver Kayser. Synthetic Strategies for Rare Cannabinoids Derived from Cannabis sativa. Journal of Natural Products 2022, 85 (6) , 1555-1568. https://doi.org/10.1021/acs.jnatprod.2c00155
    6. Yichen Li, Jiayin Dai, Lillian N. Tran, Kent E. Pinkerton, Eliot R. Spindel, Tran B. Nguyen. Vaping Aerosols from Vitamin E Acetate and Tetrahydrocannabinol Oil: Chemistry and Composition. Chemical Research in Toxicology 2022, 35 (6) , 1095-1109. https://doi.org/10.1021/acs.chemrestox.2c00064
    7. Edyta M. Greer, Victor Siev, Ayelet Segal, Alexander Greer, Charles Doubleday. Computational Evidence for Tunneling and a Hidden Intermediate in the Biosynthesis of Tetrahydrocannabinol. Journal of the American Chemical Society 2022, 144 (17) , 7646-7656. https://doi.org/10.1021/jacs.1c11981
    8. Katharina Grotsch, Valery V. Fokin. Between Science and Big Business: Tapping Mary Jane’s Uncharted Potential. ACS Central Science 2022, 8 (2) , 156-168. https://doi.org/10.1021/acscentsci.1c01100
    9. Michael A. Schafroth, Giulia Mazzoccanti, Ines Reynoso-Moreno, Reto Erni, Federica Pollastro, Diego Caprioglio, Bruno Botta, Gianna Allegrone, Giulio Grassi, Andrea Chicca, Francesco Gasparrini, Jürg Gertsch, Erick M. Carreira, Giovanni Appendino. Δ9-cis-Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology. Journal of Natural Products 2021, 84 (9) , 2502-2510. https://doi.org/10.1021/acs.jnatprod.1c00513
    10. Maria Gallo, Estefanía Moreno, Sira Defaus, Antonio Ortega-Alvaro, Angel Gonzalez, Patricia Robledo, Marco Cavaco, Vera Neves, Miguel A. R. B. Castanho, Vicent Casadó, Leonardo Pardo, Rafael Maldonado, David Andreu. Orally Active Peptide Vector Allows Using Cannabis to Fight Pain While Avoiding Side Effects. Journal of Medicinal Chemistry 2021, 64 (10) , 6937-6948. https://doi.org/10.1021/acs.jmedchem.1c00484
    11. Diego A. Rodríguez-Soacha, Julia Fender, Yesid A. Ramírez, Juan Antonio Collado, Eduardo Muñoz, Rangan Maitra, Christoph Sotriffer, Kristina Lorenz, Michael Decker. “Photo-Rimonabant”: Synthesis and Biological Evaluation of Novel Photoswitchable Molecules Derived from Rimonabant Lead to a Highly Selective and Nanomolar “Cis-On” CB1R Antagonist. ACS Chemical Neuroscience 2021, 12 (9) , 1632-1647. https://doi.org/10.1021/acschemneuro.1c00086
    12. Han Peng, Fereidoon Shahidi. Cannabis and Cannabis Edibles: A Review. Journal of Agricultural and Food Chemistry 2021, 69 (6) , 1751-1774. https://doi.org/10.1021/acs.jafc.0c07472
    13. Roman C. Sarott, Alexander E. G. Viray, Patrick Pfaff, Anastasiia Sadybekov, Gabriela Rajic, Vsevolod Katritch, Erick M. Carreira, James A. Frank. Optical Control of Cannabinoid Receptor 2-Mediated Ca2+ Release Enabled by Synthesis of Photoswitchable Probes. Journal of the American Chemical Society 2021, 143 (2) , 736-743. https://doi.org/10.1021/jacs.0c08926
    14. Bei-Er Jiang, Xingwu Jiang, Qiansen Zhang, Qiuwen Liang, Zi-Liang Qiu, Xiang-Bai Sun, Jun-Jie Yang, Si Chen, Chunyang Yi, Xiaolei Chai, Mingyao Liu, Li-Fang Yu, Weiqiang Lu, Han-Kun Zhang. From a Designer Drug to the Discovery of Selective Cannabinoid Type 2 Receptor Agonists with Favorable Pharmacokinetic Profiles for the Treatment of Systemic Sclerosis. Journal of Medicinal Chemistry 2021, 64 (1) , 385-403. https://doi.org/10.1021/acs.jmedchem.0c01023
    15. Matheus Henrique Reis, Deborah Antunes, Lucianna H. S. Santos, Ana Carolina Ramos Guimarães, Ernesto Raul Caffarena. Shared Binding Mode of Perrottetinene and Tetrahydrocannabinol Diastereomers inside the CB1 Receptor May Incentivize Novel Medicinal Drug Design: Findings from an in Silico Assay. ACS Chemical Neuroscience 2020, 11 (24) , 4289-4300. https://doi.org/10.1021/acschemneuro.0c00547
    16. Meghan R. Johnston. Chemistry of Cannabis: An Interdisciplinary Course. Journal of Chemical Education 2020, 97 (12) , 4311-4315. https://doi.org/10.1021/acs.jchemed.0c00930
    17. Ahmed Haider, Luca Gobbi, Julian Kretz, Christoph Ullmer, Andreas Brink, Michael Honer, Thomas J. Woltering, Dieter Muri, Hans Iding, Markus Bürkler, Martin Binder, Christian Bartelmus, Irene Knuesel, Pal Pacher, Adrienne Müller Herde, Francesco Spinelli, Hazem Ahmed, Kenneth Atz, Claudia Keller, Markus Weber, Roger Schibli, Linjing Mu, Uwe Grether, Simon M. Ametamey. Identification and Preclinical Development of a 2,5,6-Trisubstituted Fluorinated Pyridine Derivative as a Radioligand for the Positron Emission Tomography Imaging of Cannabinoid Type 2 Receptors. Journal of Medicinal Chemistry 2020, 63 (18) , 10287-10306. https://doi.org/10.1021/acs.jmedchem.0c00778
    18. Francesco Tinto, Rosaria Villano, Magdalena Kostrzewa, Alessia Ligresti, Hannah Straker, Emiliano Manzo. Synthesis of the Major Mammalian Metabolites of THCV. Journal of Natural Products 2020, 83 (7) , 2060-2065. https://doi.org/10.1021/acs.jnatprod.9b00831
    19. Vidyasagar Maurya, Chandrakumar Appayee. Enantioselective Total Synthesis of Potent 9β-11-Hydroxyhexahydrocannabinol. The Journal of Organic Chemistry 2020, 85 (2) , 1291-1297. https://doi.org/10.1021/acs.joc.9b02962
    20. Sean I. Hwang, Nicholas G. Franconi, Michael A. Rothfuss, Kara N. Bocan, Long Bian, David L. White, Seth C. Burkert, Raymond W. Euler, Brett J. Sopher, Miranda L. Vinay, Ervin Sejdic, Alexander Star. Tetrahydrocannabinol Detection Using Semiconductor-Enriched Single-Walled Carbon Nanotube Chemiresistors. ACS Sensors 2019, 4 (8) , 2084-2093. https://doi.org/10.1021/acssensors.9b00762
    21. Samuel D. Banister, Jonathon C. Arnold, Mark Connor, Michelle Glass, Iain S. McGregor. Dark Classics in Chemical Neuroscience: Δ9-Tetrahydrocannabinol. ACS Chemical Neuroscience 2019, 10 (5) , 2160-2175. https://doi.org/10.1021/acschemneuro.8b00651
    22. Gabriel J. Reyes-Rodríguez, Nomaan M. Rezayee, Andreu Vidal-Albalat, Karl Anker Jørgensen. Prevalence of Diarylprolinol Silyl Ethers as Catalysts in Total Synthesis and Patents. Chemical Reviews 2019, 119 (6) , 4221-4260. https://doi.org/10.1021/acs.chemrev.8b00583
    23. Grete Hoffmann, Constantin G. Daniliuc, Armido Studer. Synthesis of Para (−)-Δ8-THC Triflate as a Building Block for the Preparation of THC Derivatives Bearing Different Side Chains. Organic Letters 2019, 21 (2) , 563-566. https://doi.org/10.1021/acs.orglett.8b03907
    24. Andrea L. Devereaux, Susan L. Mercer, Christopher W. Cunningham. DARK Classics in Chemical Neuroscience: Morphine. ACS Chemical Neuroscience 2018, 9 (10) , 2395-2407. https://doi.org/10.1021/acschemneuro.8b00150
    25. Grete Hoffmann, Armido Studer. Short and Protecting-Group-Free Approach to the (−)-Δ8-THC-Motif: Synthesis of THC-Analogues, (−)-Machaeriol B and (−)-Machaeriol D. Organic Letters 2018, 20 (10) , 2964-2966. https://doi.org/10.1021/acs.orglett.8b01005
    26. Federica Pollastro, Diego Caprioglio, Patrizia Marotta, Aniello Schiano Moriello, Luciano De Petrocellis, Orazio Taglialatela-Scafati, Giovanni Appendino. Iodine-Promoted Aromatization of p-Menthane-Type Phytocannabinoids. Journal of Natural Products 2018, 81 (3) , 630-633. https://doi.org/10.1021/acs.jnatprod.7b00946
    27. Zachary P. Shultz, Grant A. Lawrence, Jeffrey M. Jacobson, Emmanuel J. Cruz, and James W. Leahy . Enantioselective Total Synthesis of Cannabinoids—A Route for Analogue Development. Organic Letters 2018, 20 (2) , 381-384. https://doi.org/10.1021/acs.orglett.7b03668
    28. Francesco Spinelli, Elena Capparelli, Carmen Abate, Nicola A. Colabufo, and Marialessandra Contino . Perspectives of Cannabinoid Type 2 Receptor (CB2R) Ligands in Neurodegenerative Disorders: Structure–Affinity Relationship (SAfiR) and Structure–Activity Relationship (SAR) Studies. Journal of Medicinal Chemistry 2017, 60 (24) , 9913-9931. https://doi.org/10.1021/acs.jmedchem.7b00155
    29. Matthias V. Westphal, Michael A. Schafroth, Roman C. Sarott, Michael A. Imhof, Christian P. Bold, Philipp Leippe, Amey Dhopeshwarkar, Jessica M. Grandner, Vsevolod Katritch, Ken Mackie, Dirk Trauner, Erick M. Carreira, and James A. Frank . Synthesis of Photoswitchable Δ9-Tetrahydrocannabinol Derivatives Enables Optical Control of Cannabinoid Receptor 1 Signaling. Journal of the American Chemical Society 2017, 139 (50) , 18206-18212. https://doi.org/10.1021/jacs.7b06456
    30. David W. Christianson. Structural and Chemical Biology of Terpenoid Cyclases. Chemical Reviews 2017, 117 (17) , 11570-11648. https://doi.org/10.1021/acs.chemrev.7b00287
    31. Rareş-Petru Moldovan, Kristin Hausmann, Winnie Deuther-Conrad, and Peter Brust . Development of Highly Affine and Selective Fluorinated Cannabinoid Type 2 Receptor Ligands. ACS Medicinal Chemistry Letters 2017, 8 (5) , 566-571. https://doi.org/10.1021/acsmedchemlett.7b00129
    32. Fabiana Piscitelli, Ester Pagano, Anna Lauritano, Angelo A. Izzo, and Vincenzo Di Marzo . Development of a Rapid LC-MS/MS Method for the Quantification of Cannabidiol, Cannabidivarin, Δ9-Tetrahydrocannabivarin, and Cannabigerol in Mouse Peripheral Tissues. Analytical Chemistry 2017, 89 (8) , 4749-4755. https://doi.org/10.1021/acs.analchem.7b01094
    33. Rareş-Petru Moldovan, Rodrigo Teodoro, Yongjun Gao, Winnie Deuther-Conrad, Mathias Kranz, Yuchuan Wang, Hiroto Kuwabara, Masayoshi Nakano, Heather Valentine, Steffen Fischer, Martin G. Pomper, Dean F. Wong, Robert F. Dannals, Peter Brust, and Andrew G. Horti . Development of a High-Affinity PET Radioligand for Imaging Cannabinoid Subtype 2 Receptor. Journal of Medicinal Chemistry 2016, 59 (17) , 7840-7855. https://doi.org/10.1021/acs.jmedchem.6b00554
    34. Martín J. Riveira, Agustina La-Venia, and Mirta P. Mischne . Pericyclic Cascade toward Isochromenes: Application to the Synthesis of Alkaloid Benzosimuline. The Journal of Organic Chemistry 2016, 81 (17) , 7977-7983. https://doi.org/10.1021/acs.joc.6b01278
    35. Shuang Han, Fei-Fei Zhang, Hai-Yan Qian, Li-Li Chen, Jian-Bin Pu, Xin Xie, and Jian-Zhong Chen . Development of Quinoline-2,4(1H,3H)-diones as Potent and Selective Ligands of the Cannabinoid Type 2 Receptor. Journal of Medicinal Chemistry 2015, 58 (15) , 5751-5769. https://doi.org/10.1021/acs.jmedchem.5b00227
    36. Mohamed M. Radwan, Mahmoud A. ElSohly, Abir T. El-Alfy, Safwat A. Ahmed, Desmond Slade, Afeef S. Husni, Susan P. Manly, Lisa Wilson, Suzanne Seale, Stephen J. Cutler, and Samir A. Ross . Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa. Journal of Natural Products 2015, 78 (6) , 1271-1276. https://doi.org/10.1021/acs.jnatprod.5b00065
    37. David R. Janero and Alexandros Makriyannis . Terpenes and Lipids of the Endocannabinoid and Transient-Receptor-Potential-Channel Biosignaling Systems. ACS Chemical Neuroscience 2014, 5 (11) , 1097-1106. https://doi.org/10.1021/cn5000875
    38. Valentina Lucchesi, Dow P. Hurst, Derek M. Shore, Simone Bertini, Brandie M. Ehrmann, Marco Allarà, Lyle Lawrence, Alessia Ligresti, Filippo Minutolo, Giuseppe Saccomanni, Haleli Sharir, Marco Macchia, Vincenzo Di Marzo, Mary E. Abood, Patricia H. Reggio, and Clementina Manera . CB2-Selective Cannabinoid Receptor Ligands: Synthesis, Pharmacological Evaluation, and Molecular Modeling Investigation of 1,8-Naphthyridin-2(1H)-one-3-carboxamides. Journal of Medicinal Chemistry 2014, 57 (21) , 8777-8791. https://doi.org/10.1021/jm500807e
    39. Rimi Roy, Soumyadipta Rakshit, Tanmoy Bhowmik, Sagar Khan, Avishek Ghatak, and Sanjay Bhar . Substituted 3-E-Styryl-2H-chromenes and 3-E-Styryl-2H-thiochromenes: Synthesis, Photophysical Studies, Anticancer Activity, and Exploration to Tricyclic Benzopyran Skeleton. The Journal of Organic Chemistry 2014, 79 (14) , 6603-6614. https://doi.org/10.1021/jo5011125
    40. Alexandros Makriyannis . 2012 Division of Medicinal Chemistry Award Address. Trekking the Cannabinoid Road: A Personal Perspective. Journal of Medicinal Chemistry 2014, 57 (10) , 3891-3911. https://doi.org/10.1021/jm500220s
    41. Stephan Röver, Mirjana Andjelkovic, Agnès Bénardeau, Evelyne Chaput, Wolfgang Guba, Paul Hebeisen, Susanne Mohr, Matthias Nettekoven, Ulrike Obst, Wolfgang F. Richter, Christoph Ullmer, Pius Waldmeier, and Matthew B. Wright . 6-Alkoxy-5-aryl-3-pyridinecarboxamides, a New Series of Bioavailable Cannabinoid Receptor Type 1 (CB1) Antagonists Including Peripherally Selective Compounds. Journal of Medicinal Chemistry 2013, 56 (24) , 9874-9896. https://doi.org/10.1021/jm4010708
    42. Sangdon Han, Jayant Thatte, Daniel J. Buzard, and Robert M. Jones . Therapeutic Utility of Cannabinoid Receptor Type 2 (CB2) Selective Agonists. Journal of Medicinal Chemistry 2013, 56 (21) , 8224-8256. https://doi.org/10.1021/jm4005626
    43. Amy L. Patton, Kathryn A. Seely, Krishna C. Chimalakonda, Johnny P. Tran, Matthew Trass, Art Miranda, William E. Fantegrossi, Paul D. Kennedy, Paul Dobrowolski, Anna Radominska-Pandya, Keith R. McCain, Laura P. James, Gregory W. Endres, and Jeffery H. Moran . Targeted Metabolomic Approach for Assessing Human Synthetic Cannabinoid Exposure and Pharmacology. Analytical Chemistry 2013, 85 (19) , 9390-9399. https://doi.org/10.1021/ac4024704
    44. Sean P. Hollinshead, Michael W. Tidwell, John Palmer, Rossella Guidetti, Adam Sanderson, Michael P. Johnson, Mark G. Chambers, Jennifer Oskins, Robert Stratford, and Peter C. Astles . Selective Cannabinoid Receptor Type 2 (CB2) Agonists: Optimization of a Series of Purines Leading to the Identification of a Clinical Candidate for the Treatment of Osteoarthritic Pain. Journal of Medicinal Chemistry 2013, 56 (14) , 5722-5733. https://doi.org/10.1021/jm400305d
    45. Samuel D. Banister, Shane M. Wilkinson, Mitchell Longworth, Jordyn Stuart, Nadine Apetz, Katrina English, Lance Brooker, Catrin Goebel, David E. Hibbs, Michelle Glass, Mark Connor, Iain S. McGregor, and Michael Kassiou . The Synthesis and Pharmacological Evaluation of Adamantane-Derived Indoles: Cannabimimetic Drugs of Abuse. ACS Chemical Neuroscience 2013, 4 (7) , 1081-1092. https://doi.org/10.1021/cn400035r
    46. Yan Li, Yan-Jun Ding, Jian-Yong Wang, Yi-Ming Su, and Xi-Sheng Wang . Pd-Catalyzed C–H Lactonization for Expedient Synthesis of Biaryl Lactones and Total Synthesis of Cannabinol. Organic Letters 2013, 15 (11) , 2574-2577. https://doi.org/10.1021/ol400877q
    47. Ganesh A. Thakur, Shama Bajaj, Carol Paronis, Yan Peng, Anna L. Bowman, Lawrence S. Barak, Marc G. Caron, Demon Parrish, Jeffrey R. Deschamps, and Alexandros Makriyannis . Novel Adamantyl Cannabinoids as CB1 Receptor Probes. Journal of Medicinal Chemistry 2013, 56 (10) , 3904-3921. https://doi.org/10.1021/jm4000775
    48. Li-Jie Cheng, Jian-Hua Xie, Yong Chen, Li-Xin Wang, and Qi-Lin Zhou . Enantioselective Total Synthesis of (−)-Δ8-THC and (−)-Δ9-THC via Catalytic Asymmetric Hydrogenation and SNAr Cyclization. Organic Letters 2013, 15 (4) , 764-767. https://doi.org/10.1021/ol303351y
    49. Xiaofei Sun and Sudhansu K. Dey . Endocannabinoid Signaling in Female Reproduction. ACS Chemical Neuroscience 2012, 3 (5) , 349-355. https://doi.org/10.1021/cn300014e
    50. Dagmar C. Kapeller and Stefan Bräse . Versatile Solid-Phase Synthesis of Chromenes Resembling Classical Cannabinoids. ACS Combinatorial Science 2011, 13 (5) , 554-561. https://doi.org/10.1021/co200107s
    51. Krishna C. Chimalakonda, Cindy L. Moran, Paul D. Kennedy, Gregory W. Endres, Adam Uzieblo, Paul J. Dobrowolski, E. Kim Fifer, Jeff Lapoint, Lewis S. Nelson, Robert S. Hoffman, Laura P. James, Anna Radominska-Pandya, and Jeffery H. Moran . Solid-Phase Extraction and Quantitative Measurement of Omega and Omega-1 Metabolites of JWH-018 and JWH-073 in Human Urine. Analytical Chemistry 2011, 83 (16) , 6381-6388. https://doi.org/10.1021/ac201377m
    52. Cindy L. Moran, Vi-Huyen Le, Krishna C. Chimalakonda, Amy L. Smedley, Felisia D. Lackey, Suzanne N. Owen, Paul D. Kennedy, Gregory W. Endres, Fred L. Ciske, James B. Kramer, Andrei M. Kornilov, L. D. Bratton, Paul J. Dobrowolski, William D. Wessinger, William E. Fantegrossi, Paul L. Prather, Laura P. James, Anna Radominska-Pandya, and Jeffery H. Moran . Quantitative Measurement of JWH-018 and JWH-073 Metabolites Excreted in Human Urine. Analytical Chemistry 2011, 83 (11) , 4228-4236. https://doi.org/10.1021/ac2005636
    53. Sean R. Donohue, Robert F. Dannals, Christer Halldin, and Victor W. Pike . N-(4-Cyanotetrahydro-2H-pyran-4-yl) and N-(1-Cyanocyclohexyl) Derivatives of 1,5-Diarylpyrazole-3-carboxamides Showing High Affinity for 18 kDa Translocator Protein and/or Cannabinoid Receptors. Journal of Medicinal Chemistry 2011, 54 (8) , 2961-2970. https://doi.org/10.1021/jm2000536
    54. Sangmi Oh, Hwan Jong Jang, Sung Kon Ko, Yeonjin Ko and Seung Bum Park . Construction of a Polyheterocyclic Benzopyran Library with Diverse Core Skeletons through Diversity-Oriented Synthesis Pathway. Journal of Combinatorial Chemistry 2010, 12 (4) , 548-558. https://doi.org/10.1021/cc100044w
    55. Jennifer E. Murray and Rick A. Bevins . Cannabinoid Conditioned Reward and Aversion: Behavioral and Neural Processes. ACS Chemical Neuroscience 2010, 1 (4) , 265-278. https://doi.org/10.1021/cn100005p
    56. Mark Seierstad and J. Guy Breitenbucher. Discovery and Development of Fatty Acid Amide Hydrolase (FAAH) Inhibitors. Journal of Medicinal Chemistry 2008, 51 (23) , 7327-7343. https://doi.org/10.1021/jm800311k
    57. Sean R. Donohue, Victor W. Pike, Sjoerd J. Finnema, Phong Truong, Jan Andersson, Balázs Gulyás and Christer Halldin . Discovery and Labeling of High-Affinity 3,4-Diarylpyrazolines as Candidate Radioligands for In Vivo Imaging of Cannabinoid Subtype-1 (CB1) Receptors. Journal of Medicinal Chemistry 2008, 51 (18) , 5608-5616. https://doi.org/10.1021/jm800329z
    58. Mingfeng Bai, Michelle Sexton, Nephi Stella and Darryl J. Bornhop. MBC94, a Conjugable Ligand for Cannabinoid CB2 Receptor Imaging. Bioconjugate Chemistry 2008, 19 (5) , 988-992. https://doi.org/10.1021/bc700419e
    59. Safwat A. Ahmed, Samir A. Ross, Desmond Slade, Mohamed M. Radwan, Fazila Zulfiqar and Mahmoud A. ElSohly. Cannabinoid Ester Constituents from High-Potency Cannabis sativa. Journal of Natural Products 2008, 71 (4) , 536-542. https://doi.org/10.1021/np070454a
    60. Serdar Durdagi,, Agnes Kapou,, Therapia Kourouli,, Thanos Andreou,, Spyros P. Nikas,, Victoria R. Nahmias,, Demetris P. Papahatjis,, Manthos G. Papadopoulos, and, Thomas Mavromoustakos. The Application of 3D-QSAR Studies for Novel Cannabinoid Ligands Substituted at the C1‘ Position of the Alkyl Side Chain on the Structural Requirements for Binding to Cannabinoid Receptors CB1 and CB2. Journal of Medicinal Chemistry 2007, 50 (12) , 2875-2885. https://doi.org/10.1021/jm0610705
    61. Barry M. Trost and, Kalindi Dogra. Synthesis of (-)-Δ9-trans-Tetrahydrocannabinol:  Stereocontrol via Mo-Catalyzed Asymmetric Allylic Alkylation Reaction. Organic Letters 2007, 9 (5) , 861-863. https://doi.org/10.1021/ol063022k
    62. Lisa M. Eubanks,, Claude J. Rogers,, Albert E. Beuscher IV,, George F. Koob,, Arthur J. Olson,, Tobin J. Dickerson, and, Kim D. Janda. A Molecular Link between the Active Component of Marijuana and Alzheimer's Disease Pathology. Molecular Pharmaceutics 2006, 3 (6) , 773-777. https://doi.org/10.1021/mp060066m
    63. Elena Motti,, Fiorenza Faccini,, Ilaria Ferrari,, Marta Catellani, and, Raffaella Ferraccioli. Sequential Unsymmetrical Aryl Coupling of o-Substituted Aryl Iodides with o-Bromophenols and Reaction with Olefins:  Palladium-Catalyzed Synthesis of 6H-Dibenzopyran Derivatives. Organic Letters 2006, 8 (18) , 3967-3970. https://doi.org/10.1021/ol061443w
    64. Tiziano Tuccinardi,, Pier Luigi Ferrarini,, Clementina Manera,, Gabriella Ortore,, Giuseppe Saccomanni, and, Adriano Martinelli. Cannabinoid CB2/CB1 Selectivity. Receptor Modeling and Automated Docking Analysis. Journal of Medicinal Chemistry 2006, 49 (3) , 984-994. https://doi.org/10.1021/jm050875u
    65. Eric Stern,, Giulio G. Muccioli,, Régis Millet,, Jean-François Goossens,, Amaury Farce,, Philippe Chavatte,, Jacques H. Poupaert,, Didier M. Lambert,, Patrick Depreux, and, Jean-Pierre Hénichart. Novel 4-Oxo-1,4-dihydroquinoline-3-carboxamide Derivatives as New CB2 Cannabinoid Receptors Agonists:  Synthesis, Pharmacological Properties and Molecular Modeling. Journal of Medicinal Chemistry 2006, 49 (1) , 70-79. https://doi.org/10.1021/jm050467q
    66. Outi M. H. Salo,, Juha R. Savinainen,, Teija Parkkari,, Tapio Nevalainen,, Maija Lahtela-Kakkonen,, Jukka Gynther,, Jarmo T. Laitinen,, Tomi Järvinen, and, Antti Poso. 3D-QSAR Studies on Cannabinoid CB1 Receptor Agonists:  G-Protein Activation as Biological Data. Journal of Medicinal Chemistry 2006, 49 (2) , 554-566. https://doi.org/10.1021/jm0505157
    67. Antonella Brizzi,, Vittorio Brizzi,, Maria Grazia Cascio,, Tiziana Bisogno,, Rossella Sirianni, and, Vincenzo Di Marzo. Design, Synthesis, and Binding Studies of New Potent Ligands of Cannabinoid Receptors. Journal of Medicinal Chemistry 2005, 48 (23) , 7343-7350. https://doi.org/10.1021/jm0501533
    68. Longwu Qi,, Noboru Yamamoto,, Michael M. Meijler,, Laurence J. Altobell, III,, George F. Koob,, Peter Wirsching, and, Kim D. Janda. Δ9-Tetrahydrocannabinol Immunochemical Studies:  Haptens, Monoclonal Antibodies, and a Convenient Synthesis of Radiolabeled Δ9-Tetrahydrocannabinol. Journal of Medicinal Chemistry 2005, 48 (23) , 7389-7399. https://doi.org/10.1021/jm050442r
    69. Outi M. H. Salo,, Katri H. Raitio,, Juha R. Savinainen,, Tapio Nevalainen,, Maija Lahtela-Kakkonen,, Jarmo T. Laitinen,, Tomi Järvinen, and, Antti Poso. Virtual Screening of Novel CB2 Ligands Using a Comparative Model of the Human Cannabinoid CB2 Receptor. Journal of Medicinal Chemistry 2005, 48 (23) , 7166-7171. https://doi.org/10.1021/jm050565b
    70. Didier M. Lambert and, Christopher J. Fowler. The Endocannabinoid System: Drug Targets, Lead Compounds, and Potential Therapeutic Applications. Journal of Medicinal Chemistry 2005, 48 (16) , 5059-5087. https://doi.org/10.1021/jm058183t
    71. Dai Lu,, Zhaoxing Meng,, Ganesh A. Thakur,, Pusheng Fan,, John Steed,, Cindy L. Tartal,, Dow P. Hurst,, Patricia H. Reggio,, Jeffrey R. Deschamps,, Damon A. Parrish,, Clifford George,, Torbjörn U. C. Järbe,, Richard J. Lamb, and, Alexandros Makriyannis. Adamantyl Cannabinoids:  A Novel Class of Cannabinergic Ligands. Journal of Medicinal Chemistry 2005, 48 (14) , 4576-4585. https://doi.org/10.1021/jm058175c
    72. Outi M. H. Salo,, Maija Lahtela-Kakkonen,, Jukka Gynther,, Tomi Järvinen, and, Antti Poso. Development of a 3D Model for the Human Cannabinoid CB1 Receptor. Journal of Medicinal Chemistry 2004, 47 (12) , 3048-3057. https://doi.org/10.1021/jm031052c
    73. María L. López-Rodríguez,, Alma Viso,, Silvia Ortega-Gutiérrez,, Christopher J. Fowler,, Gunnar Tiger,, Eva de Lago,, Javier Fernández-Ruiz, and, José A. Ramos. Design, Synthesis, and Biological Evaluation of New Inhibitors of the Endocannabinoid Uptake:  Comparison with Effects on Fatty Acid Amidohydrolase. Journal of Medicinal Chemistry 2003, 46 (8) , 1512-1522. https://doi.org/10.1021/jm0210818
    74. Ma. Elena Y. Francisco,, Herbert H. Seltzman,, Anne F. Gilliam,, René A. Mitchell,, Sharyl L. Rider,, Roger G. Pertwee,, Lesley A. Stevenson, and, Brian F. Thomas. Synthesis and Structure−Activity Relationships of Amide and Hydrazide Analogues of the Cannabinoid CB1 Receptor Antagonist N-(Piperidinyl)- 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716). Journal of Medicinal Chemistry 2002, 45 (13) , 2708-2719. https://doi.org/10.1021/jm010498v
    75. Frédéric Ooms,, Johan Wouters,, Olivier Oscari,, Thierry Happaerts,, Géraldine Bouchard,, Pierre-Alain Carrupt,, Bernard Testa, and, Didier M. Lambert. Exploration of the Pharmacophore of 3-Alkyl-5-Arylimidazolidinediones as New CB1 Cannabinoid Receptor Ligands and Potential Antagonists: Synthesis, Lipophilicity, Affinity, and Molecular Modeling. Journal of Medicinal Chemistry 2002, 45 (9) , 1748-1756. https://doi.org/10.1021/jm010896y
    76. Maria Fichera,, Gabriele Cruciani,, Alfredo Bianchi, and, Giuseppe Musumarra. A 3D-QSAR Study on the Structural Requirements for Binding to CB1 and CB2 Cannabinoid Receptors. Journal of Medicinal Chemistry 2000, 43 (12) , 2300-2309. https://doi.org/10.1021/jm991074s
    77. Xiang-Qun Xie,, Spiro Pavlopoulos,, C. M. DiMeglio, and, Alexandros Makriyannis. Conformational Studies on a Diastereoisomeric Pair of Tricyclic Nonclassical Cannabinoids by NMR Spectroscopy and Computer Molecular Modeling. Journal of Medicinal Chemistry 1998, 41 (2) , 167-174. https://doi.org/10.1021/jm960410r
    78. Man-Hee Rhee,, Zvi Vogel,, Jacob Barg,, Michael Bayewitch,, Rivka Levy,, Lumir Hanuš,, Aviva Breuer, and, Raphael Mechoulam. Cannabinol Derivatives:  Binding to Cannabinoid Receptors and Inhibition of Adenylylcyclase. Journal of Medicinal Chemistry 1997, 40 (20) , 3228-3233. https://doi.org/10.1021/jm970126f
    79. Tzviel Sheskin,, Lumir Hanuš,, Joram Slager,, Zvi Vogel, and, Raphael Mechoulam. Structural Requirements for Binding of Anandamide-Type Compounds to the Brain Cannabinoid Receptor. Journal of Medicinal Chemistry 1997, 40 (5) , 659-667. https://doi.org/10.1021/jm960752x
    80. Erin M. Rock, Linda A. Parker. The role of anandamide and the endocannabinoids in the treatment and regulation of nausea and vomiting. 2025, 475-493. https://doi.org/10.1016/B978-0-443-19081-0.00005-6
    81. Raesham Mahmood, Claudia Poluga, Isabelle Boileau, Laura M. Best. A brief review of anandamide in cannabis use and cannabis use disorder. 2025, 285-328. https://doi.org/10.1016/B978-0-443-19081-0.00009-3
    82. Cristian Caprari, Elena Ferri, Maria Angela Vandelli, Cinzia Citti, Giuseppe Cannazza. An emerging trend in Novel Psychoactive Substances (NPSs): designer THC. Journal of Cannabis Research 2024, 6 (1) https://doi.org/10.1186/s42238-024-00226-y
    83. Husam A. ALSalamat, Sara Feras Abuarab, Hazem Mohamed Salamah, Anas Hasan Ishqair, Mohammad Fuad Dwikat, Anas Zakarya Nourelden, Aseel N. Qandil, Yasmeen Barakat, Muna Barakat. Cannabis and cancer: unveiling the potential of a green ally in breast, colorectal, and prostate cancer. Journal of Cannabis Research 2024, 6 (1) https://doi.org/10.1186/s42238-024-00233-z
    84. Fatima-Zahrae Laaboudi, Mohamed Rejdali, Hassan Amhamdi, Amin Salhi, Abedellah Elyoussfi, M.’hamed Ahari. In the weeds: A comprehensive review of cannabis; its chemical complexity, biosynthesis, and healing abilities. Toxicology Reports 2024, 13 , 101685. https://doi.org/10.1016/j.toxrep.2024.101685
    85. Carlos A. Aguirre-Rodríguez, Alfonso Delgado, Alberto Alatorre, Aldo Oviedo-Chávez, José R. Martínez-Escudero, Rafael Barrientos, Enrique Querejeta. Local activation of CB1 receptors by synthetic and endogenous cannabinoids dampens burst firing mode of reticular thalamic nucleus neurons in rats under ketamine anesthesia. Experimental Brain Research 2024, 242 (9) , 2137-2157. https://doi.org/10.1007/s00221-024-06889-6
    86. Carissa Nelson, Christian Fischer-Lodike, James S. Chickos. Estimation of the Vaporization Enthalpies and Vapor Pressures of α-Tocopherol and Δ9-Tetrahydrocannabinol via the Use of a Surrogate, Correlation Gas Chromatography, and Synthetic and Retrosynthetic Analysis. Molecules 2024, 29 (18) , 4332. https://doi.org/10.3390/molecules29184332
    87. Bismarck Rezende, Kethely Lima Marques, Filipe Eloi Alves de Carvalho, Vitória Macario de Simas Gonçalves, Barbara Conceição Costa Azeredo de Oliveira, Gabriela Guedes Nascimento, Yure Bazilio dos Santos, Fernanda Antunes, Penha Cristina Barradas, Fabrícia Lima Fontes-Dantas, Guilherme Carneiro Montes. Cannabigerol Reduces Acute and Chronic Hypernociception in Animals Exposed to Prenatal Hypoxia-Ischemia. Scientia Pharmaceutica 2024, 92 (3) , 53. https://doi.org/10.3390/scipharm92030053
    88. Scott H. Gillham, Paige L. Cole, Mark R. Viggars, Andy H. Nolan, Graeme L. Close, Daniel J. Owens. Comparative transcriptomics of broad‐spectrum and synthetic cannabidiol treated C 2 C 12 skeletal myotubes. Physiological Reports 2024, 12 (18) https://doi.org/10.14814/phy2.70059
    89. Cristian Caprari, Elena Ferri, Martin G. Schmid, Loretta L. Del Mercato, Cinzia Citti, Giuseppe Cannazza. Δ9-Tetrahydrocannabiphorol: Identification and quantification in recreational products. Forensic Chemistry 2024, 40 , 100595. https://doi.org/10.1016/j.forc.2024.100595
    90. Sanjeev Sreenivasan, Lydia Kaoutzani, Beatrice Ugiliweneza, Maxwell Boakye, Michael Schulder, Mayur Sharma. Cannabis and Craniotomy for Glioblastoma: Impact on Complications and Health Care Utilization. World Neurosurgery 2024, https://doi.org/10.1016/j.wneu.2024.07.210
    91. Valerio Ricci, Domenico de Berardis, Giovanni Martinotti, Giuseppe Maina. Neurotrophic Factors in Cannabis-induced Psychosis: An Update. Current Topics in Medicinal Chemistry 2024, 24 (20) , 1757-1772. https://doi.org/10.2174/1568026623666230829152150
    92. Miroslav Kosar, Leonard Mach, Erick M. Carreira, Marc Nazaré, Pal Pacher, Uwe Grether. Patent review of cannabinoid receptor type 2 (CB 2 R) modulators (2016-present). Expert Opinion on Therapeutic Patents 2024, 34 , 1-36. https://doi.org/10.1080/13543776.2024.2368745
    93. Jermaine D. Jones, Caroline A. Arout, Rachel Luba, Dillon Murugesan, Gabriela Madera, Liam Gorsuch, Rebecca Schusterman, Suky Martinez. The influence of drug class on reward in substance use disorders. Pharmacology Biochemistry and Behavior 2024, 240 , 173771. https://doi.org/10.1016/j.pbb.2024.173771
    94. Jonasz Dragon, Ewa Obuchowicz. How depression and antidepressant drugs affect endocannabinoid system?—review of clinical and preclinical studies. Naunyn-Schmiedeberg's Archives of Pharmacology 2024, 397 (7) , 4511-4536. https://doi.org/10.1007/s00210-023-02938-z
    95. Volatiana Rakotoarivelo, Thomas Z. Mayer, Mélissa Simard, Nicolas Flamand, Vincenzo Di Marzo. The Impact of the CB2 Cannabinoid Receptor in Inflammatory Diseases: An Update. Molecules 2024, 29 (14) , 3381. https://doi.org/10.3390/molecules29143381
    96. Pedram Shafiei-Jahani, Shi Yan, Mohammad H. Kazemi, Xin Li, Amitis Akbari, Kei Sakano, Yoshihiro Sakano, Benjamin P. Hurrell, Omid Akbari. CB2 stimulation of adipose resident ILC2s orchestrates immune balance and ameliorates type 2 diabetes mellitus. Cell Reports 2024, 43 (7) , 114434. https://doi.org/10.1016/j.celrep.2024.114434
    97. Ryan Renaldo Hall, Damian Hugh Cohall. The Relationship between Muscarinic and Cannabinoid Receptors in Neuronal Excitability and Epilepsy: A Review. Medical Cannabis and Cannabinoids 2024, , 1-1. https://doi.org/10.1159/000538297
    98. Roberta Horst, Lucas Marques, Victor Otani, Marsal Sanches, Ricardo Uchida. Cannabis Hyperemesis Syndrome: Case Study. 2024https://doi.org/10.21203/rs.3.rs-4278654/v1
    99. Cengizhan Keski. The Synthetic Cannabinoids. Eurasian Journal of Toxicology 2024, 6 (1) , 6-11. https://doi.org/10.51262/ejtox.1463809
    100. Orrin Devinsky, Nicholas A. Jones, Mark O. Cunningham, B. Ashan P. Jayasekera, Sasha Devore, Benjamin J. Whalley. Cannabinoid treatments in epilepsy and seizure disorders. Physiological Reviews 2024, 104 (2) , 591-649. https://doi.org/10.1152/physrev.00049.2021
    Load more citations

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 1964, 86, 8, 1646–1647
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja01062a046
    Published April 1, 1964

    Article Views

    7079

    Altmetric

    -

    Citations

    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.