title: The role of fluorine substitution in the structure-activity relationships (SAR) of classical cannabinoids.
abstract: A facile synthesis of 1-fluoro-1-deoxy-Delta(8)-THC analogs with side chains seven carbons in length, in the alkane/ene/yne- series (6, 5, and 4), was achieved from 1-fluoro-3,5-dimethoxybenzene (1). In vitro studies show that substitution by a fluorine has a significant detrimental effect on CB1 binding which is supported by in vivo testing. The implications of these results on the SAR of classical cannabinoids are discussed.
authors.affiliation: Organix Inc., 240 Salem Street, Woburn, MA 01801, USA.
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Crocker
authors.forename: Anu
authors.initials: A
authors.lastname: Mahadevan
authors.forename: Jenny L
authors.initials: JL
authors.lastname: Wiley
authors.forename: Billy R
authors.initials: BR
authors.lastname: Martin
authors.forename: Raj K
authors.initials: RK
authors.lastname: Razdan
mesh_terms: D000818:Animals; D001831:Body Temperature / Q000187:drug effects; D002186:Cannabinoids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D005461:Fluorine / Q000737:chemistry*; D007202:Indicators and Reagents; D051379:Mice; D009043:Motor Activity / Q000187:drug effects; D011930:Reaction Time / Q000187:drug effects; D043884:Receptor, Cannabinoid, CB1 / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D002186:Cannabinoids; D007202:Indicators and Reagents; D043884:Receptor, Cannabinoid, CB1; D005461:Fluorine