Tropatepine

Tropatepine

Clinical data
Trade names	Lepticur
AHFS/Drugs.com	International Drug Names
ATC code	N04AA12 ( WHO )
Identifiers
IUPAC name (1S,5S)-3-dibenzo[b,e]thiepin-11(6H)-ylidene-8-methyl-8-azabicyclo[3.2.1]octane
CAS Number	27574-24-9
PubChem CID	198068
ChemSpider	171431  Y
UNII	C27HY5RFU5
KEGG	D07303  Y
CompTox Dashboard (EPA)	DTXSID70865380
Chemical and physical data
Formula	C22H23NS
Molar mass	333.49 g·mol−1
3D model (JSmol)	Interactive image
SMILES S3c1ccccc1/C(c2c(cccc2)C3)=C5/CC4N(C)C(CC4)C5
InChI InChI=1S/C22H23NS/c1-23-17-10-11-18(23)13-16(12-17)22-19-7-3-2-6-15(19)14-24-21-9-5-4-8-20(21)22/h2-9,17-18H,10-14H2,1H3 Y Key:JOQKFRLFXDPXHX-UHFFFAOYSA-N Y
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Tropatepine (brand name Lepticur) is an anticholinergic used as an antiparkinsonian agent. ^[1]

Synthesis

Tropatepine can be synthesized from 3-chlorotropane (1). ^[2] A Grignard reaction between 3-chlorotropane and dibenzo[b,e]thiepin-11(6H)-one (2) followed by dehydration to the olefin produces tropatepine (3).

Synthesis of tropatepine

See also

• Muscarinic antagonist

References

1. Celsis P, Montastruc JL, Rascol O, Senard JM, Marc-Vergnes JP, Rascol A (July 1989). "Effect of tropatepine, an anticholinergic drug, on regional cerebral blood flow in patients with Parkinson's disease". Journal of Neurology, Neurosurgery, and Psychiatry. 52 (7): 917–8. doi:10.1136/jnnp.52.7.917. PMC   1031949 . PMID   2769291.
2. DE1952206 idem J Boissier, R Ratouis, U.S. patent 3,725,415 (1973 to Ind Pour La Fab Antibiotiques).