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Isolation, Structure, and Partial Synthesis of an Active Constituent of Hashish

Cite this: J. Am. Chem. Soc. 1964, 86, 8, 1646–1647
Publication Date (Print):April 1, 1964
https://doi.org/10.1021/ja01062a046
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  13. 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
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  20. 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
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  24. 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
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  27. 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
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  29. 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
  30. 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
  31. 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
  32. 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
  33. 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
  34. 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
  35. 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
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  37. 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
  38. 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
  39. 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
  40. 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
  41. 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
  42. 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
  43. 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
  44. 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
  45. 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
  46. 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
  47. 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
  48. 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
  49. 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
  50. 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
  51. 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
  52. 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
  53. 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
  54. 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
  55. 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
  56. 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
  57. 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
  58. 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
  59. 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
  60. 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
  61. 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
  62. Michael P. Cava , R. J. Spangler . 2-(Carbomethoxy)benzocyclobutenone. Synthesis of a photochemically sensitive small-ring system by a pyrolytic Wolff rearrangement. Journal of the American Chemical Society 1967, 89 (17) , 4550-4551. https://doi.org/10.1021/ja00993a070
  63. Timothy Y. Jen , Gordon Alan. Hughes , Herchel. Smith . Total synthesis of .DELTA.8-(.DELTA.1(6)-tetrahydrocannabinol, a biologically active constituent of hashish (marijuana). Journal of the American Chemical Society 1967, 89 (17) , 4551-4552. https://doi.org/10.1021/ja00993a071
  64. Raphael. Mechoulam , P. Braun , Yehiel. Gaoni . Stereospecific synthesis of (-)-.DELTA.1- and (-)-.DELTA.1(6)-tetrahydrocannabinols. Journal of the American Chemical Society 1967, 89 (17) , 4552-4554. https://doi.org/10.1021/ja00993a072
  65. Fúlvio Rieli Mendes, Cristiane dos Santos Costa, Victor Distefano Wiltenburg, Gabriela Morales-Lima, João Ariel Bonar Fernandes, Renato Filev. Classic and non‐classic psychedelics for substance use disorder: A review of their historic, past and current research. Addiction Neuroscience 2022, 3 , 100025. https://doi.org/10.1016/j.addicn.2022.100025
  66. Michael Tagen, Linda E. Klumpers. Review of delta‐8‐tetrahydrocannabinol (Δ 8 ‐THC): Comparative pharmacology with Δ 9 ‐THC. British Journal of Pharmacology 2022, 179 (15) , 3915-3933. https://doi.org/10.1111/bph.15865
  67. Noah B.C. Piper, Emily A. Whitfield, Gregory D. Stewart, Xiaomeng Xu, Sebastian G.B. Furness. Targeting appetite and satiety in diabetes and obesity, via G protein-coupled receptors. Biochemical Pharmacology 2022, 202 , 115115. https://doi.org/10.1016/j.bcp.2022.115115
  68. B. Markus Lange, Jordan J. Zager. Comprehensive inventory of cannabinoids in Cannabis sativa L.: Can we connect genotype and chemotype?. Phytochemistry Reviews 2022, 21 (4) , 1273-1313. https://doi.org/10.1007/s11101-021-09780-2
  69. Karthik Ramesh, Daniel M. Rosenbaum. Molecular basis for ligand modulation of the cannabinoid CB 1 receptor. British Journal of Pharmacology 2022, 179 (14) , 3487-3495. https://doi.org/10.1111/bph.15627
  70. Shalini Bhawal, Manjula S. Salimath. Antagonism to Protagonism: Tracing the Historical Contours of Legalization in an Emerging Industry. Journal of Business Ethics 2022, 178 (3) , 783-801. https://doi.org/10.1007/s10551-021-04813-4
  71. Burkhard Hinz, Robert Ramer. Cannabinoids as anticancer drugs: current status of preclinical research. British Journal of Cancer 2022, 127 (1) , 1-13. https://doi.org/10.1038/s41416-022-01727-4
  72. Thomas H. Lee, Daniela Cota, Carmelo Quarta. Yin-Yang control of energy balance by lipids in the hypothalamus: The endocannabinoids vs bile acids case. Biochimie 2022, 518 https://doi.org/10.1016/j.biochi.2022.07.006
  73. Keyvan Soltan, Behnoush Dadkhah. Studies of the Major Gene Expression and Related Metabolites in Cannabinoids Biosynthesis Pathway Influenced by Ascorbic Acid. Planta Medica International Open 2022, 9 (01) , e116-e122. https://doi.org/10.1055/a-1809-7862
  74. Farah Meah, Michelle Lundholm, Nicholas Emanuele, Hafsa Amjed, Caroline Poku, Lily Agrawal, Mary Ann Emanuele. The effects of cannabis and cannabinoids on the endocrine system. Reviews in Endocrine and Metabolic Disorders 2022, 23 (3) , 401-420. https://doi.org/10.1007/s11154-021-09682-w
  75. Ammaar H. Abidi, Sahar S. Alghamdi, Karen Derefinko. A critical review of cannabis in medicine and dentistry: A look back and the path forward. Clinical and Experimental Dental Research 2022, 8 (3) , 613-631. https://doi.org/10.1002/cre2.564
  76. Wanuttha Boonyayothin, Khwanlada Kobtrakul, Petlada Khositanon, Sornkanok Vimolmangkang, Waranyoo Phoolcharoen. Development of a plant-produced recombinant monoclonal antibody against Δ-9-tetrahydrocannabinol (Δ9-THC) for immunoassay application. Biotechnology Reports 2022, 34 , e00725. https://doi.org/10.1016/j.btre.2022.e00725
  77. Mona F El-Azab, Ahmed E Wakiel, Yossef K Nafea, Mahmoud E Youssef. Role of cannabinoids and the endocannabinoid system in modulation of diabetic cardiomyopathy. World Journal of Diabetes 2022, 13 (5) , 387-407. https://doi.org/10.4239/wjd.v13.i5.387
  78. Petr Jirasek, Alexandr Jusku, Vilim Simanek, Jana Frankova, Jan Storch, Jan Vacek. Cannabidiol and periodontal inflammatory disease: A critical assessment. Biomedical Papers 2022, 166 (2) , 155-160. https://doi.org/10.5507/bp.2022.012
  79. Thomas P. Sakmar. Getting to the heart of cannabis health risks. Cell 2022, 185 (10) , 1623-1625. https://doi.org/10.1016/j.cell.2022.04.018
  80. Sung Huang Laurent Tsai, Chun-Ru Lin, Shih-Chieh Shao, Chao-Hua Fang, Tsai-Sheng Fu, Tung-Yi Lin, Yu-Chiang Hung. Cannabinoid Use for Pain Reduction in Spinal Cord Injuries: A Meta-Analysis of Randomized Controlled Trials. Frontiers in Pharmacology 2022, 13 https://doi.org/10.3389/fphar.2022.866235
  81. Shiri Procaccia, Gil Moshe Lewitus, Carni Lipson Feder, Anna Shapira, Paula Berman, David Meiri. Cannabis for Medical Use: Versatile Plant Rather Than a Single Drug. Frontiers in Pharmacology 2022, 13 https://doi.org/10.3389/fphar.2022.894960
  82. . Applications in Organic Synthesis. 2022,,, 301-323. https://doi.org/10.1002/9783527345939.ch10
  83. Carl Erwin B. Rodriguez, Lisa Ouyang, Ram Kandasamy. Antinociceptive effects of minor cannabinoids, terpenes and flavonoids in Cannabis. Behavioural Pharmacology 2022, 33 (2&3) , 130-157. https://doi.org/10.1097/FBP.0000000000000627
  84. Julio Raul Chavez-Monteagudo, José Antonio Ibancovichi, Pedro Sanchez-Aparicio, Sergio Recillas-Morales, Jorge Osorio-Avalos, Marco Antonio De Paz-Campos. Minimum Alveolar Concentration of Isoflurane in Rats Chronically Treated with the Synthetic Cannabinoid WIN 55,212-2. Animals 2022, 12 (7) , 853. https://doi.org/10.3390/ani12070853
  85. Martin Helcman, Karel Šmejkal. Biological activity of Cannabis compounds: a modern approach to the therapy of multiple diseases. Phytochemistry Reviews 2022, 21 (2) , 429-470. https://doi.org/10.1007/s11101-021-09777-x
  86. Saeideh Karimi-Haghighi, Yasaman Razavi, Daniela Iezzi, Andrew F. Scheyer, Olivier Manzoni, Abbas Haghparast. Cannabidiol and substance use disorder: Dream or reality. Neuropharmacology 2022, 207 , 108948. https://doi.org/10.1016/j.neuropharm.2022.108948
  87. Guillermo Moreno-Sanz, Alvaro Madiedo, Paula Hernandez, Janosch Kratz, Oier Aizpurua-Olaizola, Matthew R. D. Brown, Juan R. López, Jorge Patiño, Fredy O. Mendivelso. Sex-Dependent Prescription Patterns and Clinical Outcomes Associated With the Use of Two Oral Cannabis Formulations in the Multimodal Management of Chronic Pain Patients in Colombia. Frontiers in Pain Research 2022, 3 https://doi.org/10.3389/fpain.2022.854795
  88. G Mani, B Srinivasa Rao, M N V G A Deepthi, Chitturi Prasad. AI in Terpenes Categorization using: GC and MS Cycles. 2022,,, 1745-1750. https://doi.org/10.1109/ICEARS53579.2022.9752228
  89. Hebah Muhsien Sabiah AL Ubeed, Ronald B. H. Wills, Jayani Chandrapala. Post-Harvest Operations to Generate High-Quality Medicinal Cannabis Products: A Systemic Review. Molecules 2022, 27 (5) , 1719. https://doi.org/10.3390/molecules27051719
  90. Wenger Tibor, Kazuhito Watanabe, Yui Sasaki, Keiko Kanazawa, Koichi Shimizu, Supaart Sirikantaramas, Yoshinari Shoyama, Futoshi Taura, Satoshi Morimoto, Yukihiro Shoyama. Overview of Cannabis including Kampo Medicine and Therapy for Treatment of Dementia: A Review. Frontiers in Pharmacology 2022, 12 https://doi.org/10.3389/fphar.2021.713228
  91. Megan Malach, Igor Kovalchuk, Olga Kovalchuk. Medical Cannabis in Pediatric Oncology: Friend or Foe?. Pharmaceuticals 2022, 15 (3) , 359. https://doi.org/10.3390/ph15030359
  92. Henry L. Blanton, Melissa C. McHann, Haley De Selle, Canice Lei Dancel, Jose-Luis Redondo, Deborah Molehin, Nadezhda A. German, Scott Trasti, Kevin Pruitt, Isabel Castro-Piedras, Josée Guindon. Chronic Administration of Cannabinoid Receptor 2 Agonist (JWH-133) Increases Ectopic Ovarian Tumor Growth and Endocannabinoids (Anandamide and 2-Arachidonoyl Glycerol) Levels in Immunocompromised SCID Female Mice. Frontiers in Pharmacology 2022, 13 https://doi.org/10.3389/fphar.2022.823132
  93. Lia P. Iglesias, Daniele C. Aguiar, Fabrício A. Moreira. TRPV1 blockers as potential new treatments for psychiatric disorders. Behavioural Pharmacology 2022, 33 (1) , 2-14. https://doi.org/10.1097/FBP.0000000000000603
  94. Krzysztof Laudanski, Justin Wain. Considerations for Cannabinoids in Perioperative Care by Anesthesiologists. Journal of Clinical Medicine 2022, 11 (3) , 558. https://doi.org/10.3390/jcm11030558
  95. Gjoshe Stefkov, Ivana Cvetkovikj Karanfilova, Veronika Stoilkovska Gjorgievska, Ana Trajkovska, Nikola Geskovski, Marija Karapandzova, Svetlana Kulevanova. Analytical Techniques for Phytocannabinoid Profiling of Cannabis and Cannabis-Based Products—A Comprehensive Review. Molecules 2022, 27 (3) , 975. https://doi.org/10.3390/molecules27030975
  96. Kwang-Mook Jung, Lin Lin, Daniele Piomelli. The endocannabinoid system in the adipose organ. Reviews in Endocrine and Metabolic Disorders 2022, 23 (1) , 51-60. https://doi.org/10.1007/s11154-020-09623-z
  97. Pierre‐Louis Raux, Guillaume Drutel, Jean‐Michel Revest, Monique Vallée. New perspectives on the role of the neurosteroid pregnenolone as an endogenous regulator of type‐1 cannabinoid receptor (CB1R) activity and function. Journal of Neuroendocrinology 2022, 34 (2) https://doi.org/10.1111/jne.13034
  98. Chinedu P. Anokwuru, Felix L. Makolo, Maxleene Sandasi, Sidonie Y. Tankeu, Ishaku L. Elisha, Clement Agoni, Sandra Combrinck, Alvaro Viljoen. Cannabigerol: a bibliometric overview and review of research on an important phytocannabinoid. Phytochemistry Reviews 2022, 406 https://doi.org/10.1007/s11101-021-09794-w
  99. Yuqi Xin, Anqun Tang, Shuting Pan, Jie Zhang. Components of the Endocannabinoid System and Effects of Cannabinoids Against Bone Diseases: A Mini-Review. Frontiers in Pharmacology 2022, 12 https://doi.org/10.3389/fphar.2021.793750
  100. Yuki Sugaya, Masanobu Kano. Endocannabinoid-Mediated Control of Neural Circuit Excitability and Epileptic Seizures. Frontiers in Neural Circuits 2022, 15 https://doi.org/10.3389/fncir.2021.781113
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