Enadoline is a drug which acts as a highly selective κ-opioid agonist.

In human studies, it produced visual distortions and feelings of dissociation, reminiscent of the effects of Salvinorin A.

It was looked at as a potential analgesic, but abandoned because of the dose-limiting effects of dysphoria, which could be expected from a κ-opioid agonist. There was mention of its potential in treating comatose head injury or stroke victims, where that type of side effect would be immaterial.

Synthesis

See the related spiradoline since both compounds share the same intermediate and only differ from one another with respect to the final step.

Halfpenny, Paul R.; Horwell, David C.; Hughes, John; Hunter, John C.; Rees, David C. (1990). "Highly selective .kappa.-opioid analgesics. 3. Synthesis and structure-activity relationships of novel N-[2-(1-pyrrolidinyl)-4- or -5-substituted cyclohexyl]arylacetamide derivatives". Journal of Medicinal Chemistry 33 (1): 286. doi:10.1021/jm00163a047. PMID 2153208.