Tropatepine
{{Short description|Chemical compound}}
{{Drugbox
| verifiedrevid = 443461881
| IUPAC_name = (1S,5S)-3-dibenzo[b,e]thiepin-11(6H)-ylidene-8-methyl-8-azabicyclo[3.2.1]octane
| image = tropatepine.png
| tradename = Lepticur
| Drugs.com = {{drugs.com|international|tropatepine}}
| pregnancy_category =
| legal_status =
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number = 27574-24-9
| ATC_prefix = N04
| ATC_suffix = AA12
| PubChem = 198068
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 171431
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = C27HY5RFU5
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07303
| C=22 | H=23 | N=1 | S=1
| smiles = S3c1ccccc1/C(c2c(cccc2)C3)=C5/CC4N(C)C(CC4)C5
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JOQKFRLFXDPXHX-UHFFFAOYSA-N
}}
Tropatepine (brand name Lepticur) is an anticholinergic used as an antiparkinsonian agent.{{cite journal | vauthors = Celsis P, Montastruc JL, Rascol O, Senard JM, Marc-Vergnes JP, Rascol A | title = Effect of tropatepine, an anticholinergic drug, on regional cerebral blood flow in patients with Parkinson's disease | journal = Journal of Neurology, Neurosurgery, and Psychiatry | volume = 52 | issue = 7 | pages = 917–8 | date = July 1989 | pmid = 2769291 | pmc = 1031949 | doi = 10.1136/jnnp.52.7.917 }}
Synthesis
Tropatepine can be synthesized from 3-chlorotropane (1).DE1952206 idem J Boissier, R Ratouis, {{US patent|3725415}} (1973 to Ind Pour La Fab Antibiotiques). A Grignard reaction between 3-chlorotropane and dibenzo[b,e]thiepin-11(6H)-one (2) followed by dehydration to the olefin produces tropatepine (3).
See also
References
{{Reflist}}
{{Antiparkinson}}
{{Muscarinic acetylcholine receptor modulators}}
{{Tricyclics}}
Category:M1 receptor antagonists
Category:M2 receptor antagonists
Category:M3 receptor antagonists
Category:M4 receptor antagonists