Piroheptine (brand name Trimol) 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-(3-bromopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (1) and acetonitrile which react via catalysis by stannic chloride (SnCl4) to give 2-methyl-3-(10,11-dihydro-5H-dibenzo[a,d] cycloheptene-5-ylidene)-1-pyrroline (2). Quaternization of the product with ethyl iodide affords the alkyl immonium ion (3). Reduction of the Schiff base with sodium borohydride then affords the product, piroheptine (4).Yoshio Deguchi, Naomichi Kato, Hiroshi Nojima, (1969 to Fujisawa Pharmaceutical Co).
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