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Piroheptine

Chemical compound

Piroheptine

Chemical compound

| Drugs.com =

| elimination_half-life =

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).

References

References

  1. (February 1988). "Suppression of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced dopaminergic neurotoxicity in mouse brain by piroheptine and trihexyphenidyl". Journal of the Neurological Sciences.
  2. (June 1972). "Effect of piroheptine, a new antiparkinson drug, on dopamine uptake into synaptosomes from corpus striatum of rat brain". Arzneimittel-Forschung.
  3. Yoshio Deguchi, Naomichi Kato, Hiroshi Nojima, {{US patent. 3454595 (1969 to Fujisawa Pharmaceutical Co).
  4. (September 1972). "Synthesis and pharmacological properties of 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1,2-dialkylpyrrolidine derivatives". Journal of Medicinal Chemistry.
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antihistamines antiparkinsonian-agents dibenzocycloheptenes h1-receptor-antagonists muscarinic-antagonists pyrrolidines
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