Current Eye Research · 1982 · 38 citations · 9 references
MedicineMedicinal ChemistryPharmacologyClinical PharmacologyOcular PharmacologyPharmacodynamicsCannabinoid PharmacologyOcular PharmacodynamicsCannabinoid Structure-activity RelationshipsChemical Structure-activity RelationshipsIntraocular Pressure ElevationIntraocular Pressure ReductionSystemic Administration
Various cannabinoids have been tested for activity compared to delta 9-THC in reducing intraocular pressure after intravenous administration in rabbits at 0.1 mg or 1 mg/animal. Comparison of l-delta 9-, delta 8-, 11-OH-delta 9- and 11-OH- delta 8-THC indicates that minor configurational changes have only a small influence on activity with regard to induction of a fall in intraocular pressure, although 11-OH-delta 8-THC has increased activity. 8 alpha-OH-, 8 alpha-diOH- and 8 beta-diOH-delta 9-THC have little or no activity but 8 beta-OH-delta 9-THC is as active as delta 9-THC indicating that the hydroxyl group in the beta-position does not influence activity. Modification of the C5H11 alkyl side chain (3'-OH-delta 9-THC) reduced activity to 20% relative to delta 9-THC. Cannabidiol (CBD), cannabichromene, cannabigerol and olivetol had no activity, but 10-OH-CBD had some activity at 2 mg/animal. Cannabinol (CBN) had about half the activity of delta 9-THC and activity was reduced further with 1'-OH-CBN, indicating that side chain modification reduced activity. Neither delta 9-THC, nor cannabigerol, had any effect on intraocular pressure or total outflow facility in the rhesus monkey, suggesting species differences in ocular responses to cannabinoids. Further studies on modification of these compounds is warranted in order to further delineate the structure-activity relationships.
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Roger G. Pertwee · Neuroscience · 1977 · 384 citations
Delta(9)-tetrahydrocannabinol,, euphoria and intraocular pressure in man.
Purnell Wd, Gregg Jm · PubMed · 1975 · 65 citations
Stereochemical requirements for cannabinoid activity
Raphael Mechoulam, N. Lander, Tomas H. Varkony et al. · Journal of Medicinal Chemistry · 1980 · 62 citations