Characterization of three monohydroxyacid and two dihydroxyacid metabolites of delta 1-tetrahydrocannabinol in mouse liver.

Delta 1-Tetrahydrocannabinol-7-oic acid, together with its 2 inches-, 3 inches- and 6 alpha-monohydroxy and 2 inches, 6 alpha- and 3 inches, 6 alpha-dihydroxy derivatives have been characterized by combined gas chromatography and mass spectrometry in organic extracts of mouse liver following large doses of delta 1-tetrahydrocannabinol.

Relative potency of tetrahydrocannabinol derivatives on tonic immobility in chickens.

Chickens were given varying dosages of delta 3-, delta 8-, and delta 9-THC and tested for duration of tonic immobility (TI). Although all derivatives had a profound facilitation effect, delta 9-THC was the most potent. These results are unusual in that TI is a well documented fear-potentiated reaction and THC generally has tranquilization-like effects.

Anticonvulsant activity of four oxygenated cannabidiol derivatives.

A pharmacological comparison between cannabidiol (CBD) and four CBD derivatives, namely CBD-aldehyde-diacetate (I), 6-oxo-CBD-diacetate (II), 6-hydroxy-CBD-tri-acetate (III), and 9-hydroxy-CBD-triacetate (IV) was carried out in mice. Protection against maximal electroshock convulsions, potentiation of pentobarbital sleeping-time and reduction of spontaneous motor activity were the effects measured. All 5 compounds were equally potent in potentiating barbiturate sleeping time at doses ranging from 6.25 to 100 mg/kg. At 12.5 and 25 mg/kg only CBD and IV were able to decrease significantly the spontaneous motor activity. CBD, II, III and IV were also active in protecting mice against electroconvulsive shock at doses of 100-200 mg/kg, although at the larger dose CBD and compound II were the most efficient. Compound I was toxic, killing about half of the animals within 24 h after injection.