Two of the major metabolites which appear in rabbit urine after the administration of Delta(1)-tetrahydrocannabinol have been isolated and their structures have been tentatively established. The available evidence indicates that they are 7-carboxy-Delta(1)-tetrahydrocannabinols with an additional hydroxyl group on the side chain. The substances occur both free and as conjugates.

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The BF3 catalyzed cleavage of some steroidal 9a,1 la-epoxides has been studied in an attempt to induce migration of the C-10 methyl group to C-9. In the case of 9a,l la-epoxyandrost-4-ene-3,17-dione, cleavage with BF3 gas in benzene led to two major products. One of these was the required 3,lla-dihydroxy-9[3-methylestra-1,3,5(10)-triene-17-one, thus leading to a novel class of steroids and possibly opening a route to the synthesis of compounds of the cucurbitacin class. The other main product was shown to be 1la- hydroxy-9[3-androst-4,8(14)-diene-3,17-dione. A possiblestructural feature directing therearrangement pathway to these materials is proposed from the study of other epoxide rearrangements and some reported in the literature.

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