Synthesis and pharmacological activity of a phosphate ester of .DELTA.8-tetrahydrocannabinol

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Abstract
A water-soluble phosphate ester of .delta.8-tetrahydrocannabinol (.delta.8-THC) was synthesized and its pharmacological activities were examined. The cataleptogenic and thiopental sleep-potentiating effects of .DELTA.8-THC phosphate in the mouse were approximately 10 and 7% of those of .DELTA.8-THC, respectively. This phosphate showed almost the same potency and a longer duration of hypothermic effect, as compared with .DELTA.8-THC in the mouse. The acute toxicity of this phosphate was far lower than that of .DELTA.8-THC. .DELTA.8-THC phosphate was hydrolyzed with difficulty by alkaline phosphatase or mouse liver homogenate in vitro. The mode of action of the phosphate derivative was discussed in connection with this enzymatically difficult hydrolysis.

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