The design, synthesis and testing of desoxy-CBD: further evidence for a region of steric interference at the cannabinoid receptor.

  title={The design, synthesis and testing of desoxy-CBD: further evidence for a region of steric interference at the cannabinoid receptor.},
  author={Patricia H. Reggio and R D Bramblett and H Yuknavich and Herbert H Seltzman and Denise N. Fleming and Susanthi R. Fernando and Lesley A. Stevenson and Roger G. Pertwee},
  journal={Life sciences},
  volume={56 23-24},
Cannabidiol CBD, a non-psychoactive constituent of marihuana, has been reported to possess essentially no affinity for cannabinoid CB1 receptor binding sites in the brain. Our hypothesis concerning CBD's lack of affinity for the cannabinoid CB1 receptor is that CBD is not capable of clearing a region of steric interference at the CB1 receptor and thereby not able to bind to this receptor. We have previously characterized this region of steric interference at the CB1 receptor [P.H. Reggio, A.M… Expand
Cannabidiol (CBD) and its analogs: a review of their effects on inflammation.
  • S. Burstein
  • Chemistry, Medicine
  • Bioorganic & medicinal chemistry
  • 2015
Attention will be focused on the effects of CBD in the broad area of inflammation where such benefits seem likely to be developed and the medicinal chemistry of CBD, CBD receptor binding involved in controlling Inflammation, signaling events generated by CBD, downstream events affected by CBD. Expand
Blocking the Cannabinoid Receptors: Drug Candidates and Therapeutic Promises
  • G. Muccioli
  • Chemistry, Medicine
  • Chemistry & biodiversity
  • 2007
The pharmacological tools that are currently available and the animal studies supporting the therapeutic use of cannabinoid receptor antagonists and inverse agonists are described. Expand
Improved accessibility to the desoxy analogues of Δ9-tetrahydrocannabinol and cannabidiol
Desoxy analogues of Δ9-tetrahydrocannabinol (THC) and cannabidiol (CBD) have been reported to provide a novel mode of analgesia whilst avoiding the psychotropic side effects associated with mostExpand
An Overview on Medicinal Chemistry of Synthetic and Natural Derivatives of Cannabidiol
This review provides an overview of the chemical structure of natural and synthetic CBD derivatives including the molecular targets associated with these compounds. Expand
Brain Cannabinoid Systems as Targets for the Therapy of Neurological Disorders
These endogenous structures and chemicals and mechanisms are potentially new pathophysiologic substrates, and targets for novel cannabinoid treatments, of several neurological disorders. Expand
Evidence for a Role of Endocannabinoids, Astrocytes and p38 Phosphorylation in the Resolution of Postoperative Pain
It is demonstrated that endocannabinoid signaling via CB1 and CB2 receptors is necessary for the resolution of paw incision-induced behavioral hypersensitivity and for the limitation of pro-inflammatory signaling in astrocytes following surgical insult. Expand
A novel methodology for the synthesis of 1-desoxy-Δ8-tetrahydrocannabinol (THC) analogues
Abstract A versatile and efficient sequence was developed for the synthesis of 1-desoxy-Δ 8 -THC analogues and is demonstrated by the synthesis of sulfonamide analogues with an acetylene group at theExpand
Mild Generation of o-Quinone Methides. Synthesis of (-)-Hexahydrocannabinol and Dihydrocannabidiol
Abstract (-)-Hexahydrocannabinol 7 was synthesized enantioselectively under mild conditions through the ortho quinone methide mediated cyclization of the adduct of R-(+)-citronellal and theExpand
Towards cannabinoid drugs--revisited.


Characterization of a region of steric interference at the cannabinoid receptor using the active analog approach.
The results of this study provide an explanation at the molecular level for observed activity differences between cannabinoids that exhibit shape differences associated with their carbocyclic rings. Expand
A rational search for the separation of psychoactivity and analgesia in cannabinoids
Molecular mechanics calculations revealed that, in the global minimum energy conformation of (-)-9 beta-OH-HHC, the axial methyl at C-9 protrudes into the alpha face of the molecule, while theAxial hydroxyl at C/O-9 in (--9 alpha-OH,HHC protrudesinto this same face. Expand
The evidence for the existence of cannabinoid receptors.
  • R. Pertwee
  • Chemistry, Medicine
  • General pharmacology
  • 1993
The evidence for the existence of cannabinoid receptors is reviewed by considering the extent to which the putative cannabinoid receptor satisfies a set of interrelated criteria that have often been used in the past to establish whether or not the effects of other classes of drug are receptor mediated. Expand
Cross‐tolerance between delta‐9‐tetrahydrocannabinol and the cannabimimetic agents, CP 55,940, WIN 55,212‐2 and anandamide
The finding that in vivo pretreatment with delta‐9‐THC can produce tolerance not only to its own inhibitory effect on the vas deferens but also to that of three other cannabimimetic agents, suggests that this tissue would be suitable as an experimental model for investigating the mechanisms responsible for cannabinoid tolerance. Expand
SR141716A, a potent and selective antagonist of the brain cannabinoid receptor
SR141716A is the first selective and orally active antagonist of the brain cannabinoid receptor and should prove to be a powerful tool for investigating the in vivo functions of the anandamide/cannabinoid system. Expand
Conformationally restricted hybrids of CP-55,940 and HHC: Stereoselective synthesis and activity
Abstract A stereoselective total synthesis of each of the two diastereomeric C6-hydroxyethyl analogs of (−)-9-nor-9β-hydroxyhexahydrocannabinol has been reported. Control of the stereochemistry at C6Expand
Inhibitory effects of certain enantiomeric cannabinoids in the mouse vas deferens and the myenteric plexus preparation of guinea‐pig small intestine
The findings that (−)‐Δ9‐THC and (+)‐DMH are highly potent as inhibitors of the twitch response of the mouse vas deferens and guinea‐pig myenteric plexus preparation and that DMH shows considerable stereoselectivity suggest that the inhibitory effects of cannabinoids in these preparations are mediated by cannabinoid receptors. Expand
Synthese von Haschisch-Inhaltsstoffen. 4. Mitteilung
(−)-Cannabidiol has been synthesized from (+)-cis- and (+)-trans-p-menthadien-(2, 8)-ol-(1) and olivetol, using N, N-dimethylformamide dineopentyl acetal or weak acids, such as oxalic, picric, orExpand
Synthese und Chiralität des (-)-Cannabidiols Vorläufige Mitteilung
N, N-Dimethylformamide-dineopentylacetal mediates the direct formation of (-)-cannabidiol from (+)-trans- or (+)-cis-p-menthadiene-(2,8)-ol-(1) and olivetol. This reaction provides a simple syntheticExpand
Chemical Basis of Hashish Activity
Evidence is provided that, except for Δ1-tetrahydrocannabinol, no other major, psychotomimetically active compounds are present in hashish. Expand