9.ALPHA.,10.ALPHA.-Epoxyhexahydrocannabinol formation from .DELTA.9-tetrahydrocannabinol by liver microsomes of phenobarbital-treated mice and its pharmacological activities in mice.

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Abstract
9.alpha.,10.alpha.-Epoxyhexahydrocannabinol (9.alpha.,10.alpha.-EHHC) was formed from .DELTA.9-tetrahydrocannabinol (.DELTA.9-THC) by liver microsomes of mice pretreated with phenobarbital. Phamacological effects of 9.alpha.,10.alpha.-EHHC in mice were compared with those of .DELTA.9-THC using catalepsy, hypothermia, pentobarbital-induced sleep prolongation and anticonvulsant activity against pentylenetetrazol as indices. 9.alpha.,10.alpha.-EHHC was approximately equipotent with .DELTA.9-THC in the pharmacological indices except for catalepsy. The cataleptogenic effect of the epoxide was about 4 times as potent as the parent compound. 9.alpha.,10.alpha.-EHHC can apparently contribute to the pharmacological effects of .DELTA.9-THC as an active metabolite.