Piroheptine

Piroheptine (brand name Trimol) is an anticholinergic and antihistamine used as an antiparkinsonian agent.

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
(verify)

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]