Chemistry:Piroheptine
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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.[1][2]
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).[3][4]
References
- ↑ "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 83 (2–3): 161–166. February 1988. doi:10.1016/0022-510X(88)90065-2. PMID 3258627.
- ↑ "Effect of piroheptine, a new antiparkinson drug, on dopamine uptake into synaptosomes from corpus striatum of rat brain". Arzneimittel-Forschung 22 (6): 966–972. June 1972. PMID 5068358.
- ↑ Yoshio Deguchi, Naomichi Kato, Hiroshi Nojima, U.S. Patent 3,454,595 (1969 to Fujisawa Pharmaceutical Co).
- ↑ "Synthesis and pharmacological properties of 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1,2-dialkylpyrrolidine derivatives". Journal of Medicinal Chemistry 15 (9): 891–894. September 1972. doi:10.1021/jm00279a004. PMID 4403249.
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