Structure–Activity Relationships of Classical Cannabinoids

Abstract

In this chapter an overview of the more recent developments in the structure-activity relationships (SARs) of classical cannabinoids is discussed, especially the profound pharmacological effects produced by various chemical entities in the side chain at C-3, the hydroxyl at C-1, C-11, and hydroxyalkyl chains at C-6. Also cardiovascular studies point to the presence of a novel cannabinoid subtype receptor and the antagonist activity of cannabidiol has opened up new areas for research. Ligands, which had either a unique pharmacological profile, were potent agonists, partial agonists/antagonists, or were CB2 selective, were identified, generating leads with the potential to be drugs in the treatment of various diseases.

Identification of a cannabimimetic indole as a designer drug in a herbal product

“…In the past few decades, a number of analogs of Δ 9 -THC have been synthesized based on the partially reduced dibenzopyran structure of THC, and their structure-activity relationships were studied [12,13]. In the 1980s, a group at Pfi zer explored the development of analgesics using potent synthetic nontraditional cannabinoids, which lack the dibenzopyran structure present in the traditional cannabinoids but exhibit typical cannabinoid pharmacological effects [14][15][16][17][18][19][20][21][22].…”

Chemical analysis of synthetic cannabinoids as designer drugs in herbal products

“…Over the past few decades, a number of analogs of classical cannabinoids D 9 -THC have been synthesized based on its partially reduced dibenzopyran structure, and their structure-activity relationships have been studied [22,23]. In the 1980s, a group at Pfizer Inc. explored the development of analgesics using potent synthetic non-classical cannabinoids, which lack the dibenzopyran structure present in traditional cannabinoids but exhibit typical cannabinoid pharmacology [4][5][6][7][8]20,[24][25][26].…”

Δ9-Tetrahydrocannabinol and Its Major Metabolite Δ9-Tetrahydrocannabinol-11-oic Acid as 15-Lipoxygenase Inhibitors

“…Some of 9 -THC metabolites are known to be pharmacologically more active than the parent cannabinoid. 28 Thus, the effects of 9 -THC including its major metabolites, 11-OH-9 -THC and 9 -THC-11-oic acid, on 15-LOX were studied. The concentrations of cannabinoids used here (2 :M) were determined based on the IC 50 value of 9 -THC-mediated 15-LOX inhibition (Fig.…”