Attempts of Ranking in a Series of Synthetic Nonpsychotropic Cannabinoids

References

• Mechoulam , R. , Feigenbaum , J. J. , Lauder , N. , Segal , M. , Jarbe , T. U. C. , Hiltunen , A. J. and Consroe , P. 1988 . Enantomeric cannabinoids: Stereospecificity of psychotropic activity . Experientia , 44 : 762 – 764 .
   PubMedGoogle Scholar
• Gaoni , Y. and Mechoulam , R. 1964 . Isolation, structure and partial synthesis of an active constituent of hashish . J. Am. Chem. Soc. , 86 : 1646 – 1647 .
   Web of Science ®Google Scholar
• Mechoulam , R. , Braun , P. and Gaoni , Y. 1967 . A stereospecific synthesis of (-) Δ1 and (-) Δ6-tetrahydrocannabinoids . J. Am. Chem. Soc. , 89 : 4552 – 4554 .
   PubMed Web of Science ®Google Scholar
• Razdan , R. K. 1981 . “ The total synthesis of cannabinoids ” . In The Total Synthesis of Natural Products , Edited by: Simon , J. A. 185 – 262 . New York : Wiley .
   Google Scholar
• Dewey , W. L. 1986 . Cannabinoid pharmacology . Pharmacol. Rev. , 38 : 151 – 178 .
   PubMed Web of Science ®Google Scholar
• Martin , B. R. 1986 . Cellular effects of cannabinoids . Pharmacol. Rev. , 38 : 45 – 74 .
   PubMed Web of Science ®Google Scholar
• Pertwee , R. G. 1988 . The central neuropharmacology of psychotropic cannabinoids . Pharmacol. Ther. , 36 : 189 – 261 .
   PubMed Web of Science ®Google Scholar
• Devane , W. A. , Dysarz , F. A. , Johnson , M. R. , Melvin , L. S. and Howlett , A. C. 1988 . Determination and characterization of a cannabinoid receptor in a rat brain . Mol. Pharmacol. , 34 : 605 – 613 .
   PubMed Web of Science ®Google Scholar
• Munro , S. , Thomas , K. L. and Abu-Shaar , M. 1992 . Molecular characterization of a peripheral receptor for cannabinoids . Nature , 365 : 61 – 65 .
   Web of Science ®Google Scholar
• Devane , W. A. , Hanus , L. , Breuer , A. , Pertwee , R. G. , Stevenson , L. A. , Griffin , G. , Gibson , D. , Mandelbaum , A. , Etinger , A. and Mechoulam , R. 1992 . Isolation and structure of a brain constituent that binds to the cannabinoid receptor . Science , 258 : 1946 – 1949 .
   PubMed Web of Science ®Google Scholar
• Mechoulam , R. , Ben-Shabat , S. , Hanus , L. , Ligumsky , M. , Kaminski , N. E. , Schatz. , A. R. , Gopher , A. , Almong , S. , Martin , B. R. , Compton , D. R. , Pertwee , R. G. , Griffin , G. , Bayewitch , M. , Barg , J. and Vogel , Z. 1995 . Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors . Biochem. Pharmacol. , 50 : 83 – 90 .
   PubMed Web of Science ®Google Scholar
• Mechoulam , R. , Lander , N. , Breuer , A. and Zahalka , J. 1990 . Synthesis of the individual, pharmacologically distinct enantiomers of a tetrahydrocannabinol derivative . Tetrahedron: Assymmetry , 1 : 315 – 319 .
   Google Scholar
• Mechoulam , R. , Devane , W. A. and Glaser , R. 1992 . “ Cannabinoid geometry and biological activity ” . In Marijuana/Cannabinoids, Neurobiology and Neurophysiology , Edited by: Murphy , L. and Bartke , A. 1 – 33 . Boca Raton : CRC Press .
   Google Scholar
• Feigenbaum , J. J. , Bergmann , F. , Richmond , S. A. , Mechoulam , R. , Nadler , V. , Kloog , Y. and Sokolowsky , M. 1989 . Nonpsychotropic cannabinoid acts as a functional N-methyl-D-aspartate receptor blocker . Proc. Natl. Acad. Sci. U.S.A. , 86 : 9584 – 9587 .
   PubMed Web of Science ®Google Scholar
• Eshhar , N. , Striem , S. , Kohen , R. , Tirosh , O. and Biegon , A. 1995 . Neuroprotective and antioxidant activities of HU-211, a novel NMDA receptor antagonist . Eur. J. Pharmacol. , 283 : 19 – 29 .
   PubMed Web of Science ®Google Scholar
• Shohami , E. , Bass , R. , Ben-Hur , T. and Gallily , R. 1996 . Cytokine production in the brain following closed head injury, TNF-α inhibition is associated with cerebroprotection . Eur. J. Cytokine Netw. , 7 : 309
   Google Scholar
• Shohami , E. , Novikov , M. and Mechoulam , R. 1993 . A nonpsychotropic cannabinoid, HU-211, has cerebroactive effects after closed head injury . J. Neurotrauma , 10 : 109 – 119 .
   PubMed Web of Science ®Google Scholar
• Yoles , E. , Belkin , M. and Schwartz , M. 1995 . HU-211, a nonpsychotropic cannabinoid, produces short- and long-term neuroprotection after optic nerve axotomy . J. Neuro-trauma , 13 : 49 – 57 .
   Google Scholar
• Bar-Joseph , A. , Berkovitch , Y. , Adamchik , J. and Biegon , A. 1994 . Neuroprotective activity of HU-211, a novel NMDA antagonist, in global ischemia in gerbils . Mol. Chem. Neuropathol. , 23 : 125 – 135 .
   PubMedGoogle Scholar
• Brewster , M. E. , Pop , E. , Foltz , R. , Griffith , W. , Amselem , S. and Biegon , A. 1997 . Clinical pharmacokinetics of escalating i.v. doses of dexanabinol (HU-211), a neuroprotectant agent, in normal volunteers . J. Clin. Pharmacol. Ther. , 35 : 361 – 365 .
   Google Scholar
• Pop , E. 1999 . Developing cannabinoids as potential central nervous system agents . Curr. Opin. CPNS Invest. Drugs , 1 : 587 – 596 .
   Google Scholar
• Razdan , R. K. 1986 . Structure-activity relationship in cannabinoids . Pharmacol. Rev. , 38 : 75 – 149 .
   PubMed Web of Science ®Google Scholar
• Mechoulam , R. , Devane , W. A. and Glaser , R. 1992 . “ Cannabinoid geometry and biological activity. ” . In Marijuana/Cannabinoids Neurobiology and Neurophysiology , Edited by: Murphy , L. and Bartke , A. 1 – 33 . Boca Raton, FL : CRR Press .
   Google Scholar
• Thomas , B. F. , Compton , D. R. , Martin , B. R. and Semus , S. F. 1991 . Modeling the cannabinoid receptor: A three-dimensional quantitative structure-activity analysis . Mol. Pharmacol. , 40 : 656 – 665 .
   PubMedGoogle Scholar
• Schmelzer , S. , Greenidge , P. , Kovar , K. A. , sSchulze-Alexandru , M. and Folkers , G. 1997 . Structure-activity relationship of cannabinoids: a joint CoMFA and pseudoreceptor modelling study . J. Comput.-Aided. Mol. Des. , 11 : 278 – 292 .
   Google Scholar
• Fichera , M. , Cruciani , G. , Bianchi , A. and Musumarra , G. 2000 . A 3D-QSAR study on structural requirements for binding to CB1 and CB2 cannabinoid receptors . J. Med. Chem. , 43 : 2300 – 2309 .
   Google Scholar
• Bodor , N. and Huang , M.-J. 1994 . “ Computer-aided design of new drugs based on retrometabolic concepts. ” . In Computer-aided molecular design. Applications in agro-chemicals, materials and pharmaceuticals , Edited by: Reynolds , C. H. , Holloway , M. K. and Cox , H. K. Washington D.C : American Chemical Society . ACS Symposium Series, 589, 98–113.
   Google Scholar
• Bodor , N. and Buchwald , P. 1997 . Drug targeting via retrometabolic approaches . Pharmacol. Ther. , 76 : 1 – 27 .
   PubMed Web of Science ®Google Scholar
• Bodor , N. , Buchwald , P. and Huang , M.-J. 1998 . Computer assisted design of new drugs based on retrometabolic concepts . SAR QSAR Environ. Res. , 8 : 41 – 92 .
   PubMed Web of Science ®Google Scholar
• Bodor , N. , Buchwald , P. and Huang , M.-J. 1999 . “ The role of computational techniques in retrometabolic drug design strategies ” . In Computational Molecular Biology , Edited by: Leszcynski , J. 569 – 618 . Amsterdam : Elsevier .
   Google Scholar
• Nadler. , V. , Mechoulam , R. and Sokolovsky , M. 1993 . Blockage of [45Ca] influx through N-methyl-D-aspartate receptor ion channel by non-psychoactive cannabinoid HU-211 . Brain Res. , 622 : 79 – 85 .
   Google Scholar
• Dewar , M. J. S. , Zoebisch , E. G. , Healy , E. F. and Stewart , J. J. P. 1985 . AMI: a new general purpose quantum mechanical molecular model . J. Am. Chem. Soc. , 107 : 3902 – 3909 .
   Web of Science ®Google Scholar
• Bodor , N. and Huang , M.-J. 1992 . An extended version of a novel method for estimation of partition coefficients . J. Pharm. Sci. , 81 : 272 – 281 .
   PubMed Web of Science ®Google Scholar
• Bodor , N. and Huang , M.-J. 1992 . A new method for estimation of the aqueous solubility of organic compounds . J. Pharm. Sci , 81 : 954 – 960 .
   PubMed Web of Science ®Google Scholar
• Pop , E. , Liu , Z. Z. , Brewster , M. E. , Barenholz , Y. , Korablyov , V. , Mechoulam , R. , Nadler , V. and Biegon , A. 1996 . Derivatives of dexanabinol. I. Water-soluble salts of glycinate esters . Pharm. Res. , 13 : 62 – 69 .
   PubMed Web of Science ®Google Scholar
• Pop , E. , Soti , F. , Brewster , M. E. , Barenholz , Y. , Mechoulam , R. , Nadler , V. and Biegon , A. 1996 . Salts of aminoacid esters containing tertiary and quaternary cyclic nitrogen with increased water-solubility . Pharm. Res. , 13 : 469 – 475 . Derivatives of dexanabinol. II.
   Google Scholar
• Pop , E. , Soti , F. , Biegon , A. and Brewster , M. E. 1997 . Allylic and phenolic phosphate esters of dexanabinol . Org. Prep. Proced. Int. , 29 : 341 – 347 .
   Web of Science ®Google Scholar
• Pop , E. , Soti , F. and Rachwal , S. 1999 . Hemiesters of dexanabinol and their water-soluble salts . Org. Prep. Proced. Int. , 31 : 565 – 570 .
   Web of Science ®Google Scholar
• Pop , E. 2000 . Water-soluble combinations of dexanabinol: Prodrugs and analogs . Pharmazie , 55 : 167 – 171 .
   Google Scholar
• Pop , E. , Browne , C. E. , Nadler , V. , Biegon , A. and Brewster , M. E. 1996 . Neuroprotective (±) 3S, 4S Cannabinoids with Modified 5'-Side Chain . Bioorg. Med. Chem. Lett. , 6 : 1553 – 1558 .
   Google Scholar
• Pop , E. , Rachwal , S. , Soti , F. , Browne , C. , Dinculescu , A. , Biegon , A. , Nadler , V. , Mechoulam , R. and Brewster , M. E. 1996 . “ Analogs of dexanabinol (HU-211); NMDA receptor binding and activity ” . 052 New Orleans, LA. : The National Meeting of the ACS . Abstracts of Papers, Part 2, MEDI.
   Google Scholar
• Pop , E. , Brewster , M. E. , Browne , C. , Rachwal , S. , Nadler , V. , Striem , S. and Biegon , A. 1996 . “ NMDA receptor binding and neuroprotective activity of some structural analogs of dexanabinol (HU-211). ” . In Pharm. Res. , Vol. 13 , S-271 Seattle, WA : The 11-th Annual Meeting of AAPS .
   Google Scholar
• Pop , E. 2000 . Nonpsychotropic synthetic cannabinoids . Curr. Pharm. Des. , 6 : 1059 – 1075 .
   Google Scholar
• Karelson , M. , Lobanov , V. S. and Katritzky , A. R. 1996 . Quantum-chemical descriptors in QSAR/QSPR studies . Chem. Rev. , 96 : 1027 – 1043 .
   PubMed Web of Science ®Google Scholar