Piroheptine

Piroheptine

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-1-ethyl-2-methylpyrrolidine
CAS Number	16378-21-5 HCl:  16378-22-6  Y
PubChem CID	4854
ChemSpider	4688
UNII	AR6Y753ARL HCl:  4ZM573199N  Y
KEGG	D01231  Y
ChEBI	CHEBI:135287
CompTox Dashboard (EPA)	DTXSID30864672
Chemical and physical data
Formula	C22H25N
Molar mass	303.449 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCN1CCC(=C2C3=CC=CC=C3CCC4=CC=CC=C42)C1C
InChI InChI=1S/C22H25N/c1-3-23-15-14-19(16(23)2)22-20-10-6-4-8-17(20)12-13-18-9-5-7-11-21(18)22/h4-11,16H,3,12-15H2,1-2H3 Key:NKJQZSDCCLDOQH-UHFFFAOYSA-N
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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

1. Saitoh T (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. 83 (2–3): 161–166. doi:10.1016/0022-510X(88)90065-2. PMID   3258627. S2CID   25230405.
2. Ohashi T, Akita H, Tamura T, Noda K, Honda F (June 1972). "Effect of piroheptine, a new antiparkinson drug, on dopamine uptake into synaptosomes from corpus striatum of rat brain". Arzneimittel-Forschung. 22 (6): 966–972. PMID   5068358.
3. Yoshio Deguchi, Naomichi Kato, Hiroshi Nojima, U.S. patent 3,454,595 (1969 to Fujisawa Pharmaceutical Co).
4. Umio, S., Hitomi, M., Nojima, H., Kumadaki, N., Ueda, I., Kanaya, T., Deguchi, Y. (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. 15 (9): 891–894. doi:10.1021/jm00279a004. PMID   4403249.