Characterization of a region of steric interference at the cannabinoid receptor using the active analog approach
- Patricia H. Reggio
- ,
- Al M. Panu
- , and
- Scott Miles
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- Káthia M. Honório, Albérico B. F. da Silva. A study on the influence of molecular properties in the psychoactivity of cannabinoid compounds. Journal of Molecular Modeling 2005, 11 (3) , 200-209. https://doi.org/10.1007/s00894-005-0243-z
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- K.M. Honório, A.B.F. da Silva. A theoretical study on the influence of the frontier orbitals HOMO and LUMO and the size of C4 and C2 substituents in the psychoactivity of cannabinoid compounds. Journal of Molecular Structure: THEOCHEM 2002, 578 (1-3) , 111-117. https://doi.org/10.1016/S0166-1280(01)00690-X
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- D. P. Dolata, A. L. Parrill, W. P. Walters. CLEW: The Generation of Pharmacophore Hypotheses Through Machine Learning. SAR and QSAR in Environmental Research 1998, 9 (1-2) , 53-81. https://doi.org/10.1080/10629369808039149
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- D. R. Compton, L. S. Harris, A. H. Lichtman, B. R. Martin. Marihuana. 1996, 83-158. https://doi.org/10.1007/978-3-642-60963-3_3
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- Richard E. Musty, Patricia Reggio, Paul Consroe. A review of recent advances in cannabinoid research and the 1994 international symposium on cannabis and the cannabinoids. Life Sciences 1995, 56 (23-24) , 1933-1940. https://doi.org/10.1016/0024-3205(95)00173-4
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- Raphael Mechoulam, Lumir Hanuš, Billy R. Martin. Search for endogenous ligands of the cannabinoid receptor. Biochemical Pharmacology 1994, 48 (8) , 1537-1544. https://doi.org/10.1016/0006-2952(94)90197-X
- John W. Huffman, Dong Dai, Billy R. Martin, David R. Compton. Design, Synthesis and Pharmacology of Cannabimimetic Indoles. Bioorganic & Medicinal Chemistry Letters 1994, 4 (4) , 563-566. https://doi.org/10.1016/S0960-894X(01)80155-4
- P. H. Reggio. Cannabinoid Receptors and Their Ligands: Ligand—Ligand and Ligand—Receptor Modeling Approaches. , 247-281. https://doi.org/10.1007/3-540-26573-2_8