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).

File:Tropatepine synthesis.svg

See also

References