6-Hydroxy-4-[2-di-n-propylaminoethyl]indole: synthesis and dopaminergic actions

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Abstract
The title compound was proposed to be a biologically active metabolite of a dopaminergic agent, 4-[2-(di-n-propylamino)ethyl]indole. This proposed metabolite was synthesized by a multistep sequence beginning with methyl 3,5-dinitro o-toluate, and involving the Batcho-Leimgruber modification of the Reissert indole synthesis. The target compound exhibited high potency/activity in vivo in a cat cardioaccelerator nerve assay and in vitro in an isolated cat atrium assay. It manifested maximal pharmacological effect less than 5 min after i.v. administration in cats, as compared with a 20-min lag time following i.v. administration of the nonoxygenated congener. The target compound is evidently a metabolite of 4-[2-(di-n-propylamino)ethyl]indole.

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