Piroheptine

Piroheptine is an anticholinergic and antihistamine used as an antiparkinsonian agent.
Piroheptine was observed to prevent the reuptake of dopamine and is therefore a DRI.
Piroheptine comes from a family of drugs that includes pridefine and etifelmine.

Synthesis

Piroheptine can be synthesized starting from 5--10,11-dihydro-5H-dibenzocycloheptene and acetonitrile which react via catalysis by stannic chloride to give 2-methyl-3--1-pyrroline. Quaternization of the product with ethyl iodide affords the alkyl immonium ion. Reduction of the Schiff base with sodium borohydride then affords the product, piroheptine.