Drugs derived from cannabinoids. 1. Nitrogen analogs, benzopyranopyridines and benzopyranopyrroles

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Abstract
Various nitrogen analogs of .DELTA.6a,10a-tetrahydrocannabinol were synthesized. Minimum effective doses (MED50''s) and LD50''s were determined by a modified Irwin mouse screen after i.v. administration of compounds in PEG 200 polyethylene glycol-200. The most potent compounds were the propargyl allyl and chloroallyl derivatives. Overt behaviral effects (CNS depression, static ataxia and hypersensitivity) of the propargyl derivative and Roger Adams'' carbocyclic analog were similar in the mouse, cat, dog and monkey. Dichloroisoproterenol prevented and reversed many of these depressant effects but had no effect on the ataxia produced by these compounds. In antinociceptive tests, the propargyl derivative was active in the phenylquinone and Eddy hot-plate tests but was inactive in the tail-flick test.