:Tropanserin

{{Short description|Chemical compound}}

{{Distinguish|Tropisetron}}

{{Drugbox

| IUPAC_name = [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3,5-dimethylbenzoate

| image = Tropanserin.svg

| CAS_number = 85181-40-4

| CAS_supplemental =
{{CAS|85181-38-0}} (HCl)

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 04B48I6VHR

| ATC_prefix = None

| ATC_suffix =

| PubChem = 68600

| ChemSpiderID = 19969918

| C=17 | H=23 | N=1 | O=2

| smiles = CN3[C@H]1CC[C@@H]3C[C@@H](C1)OC(=O)c2cc(C)cc(C)c2

| StdInChI = 1S/C17H23NO2/c1-11-6-12(2)8-13(7-11)17(19)20-16-9-14-4-5-15(10-16)18(14)3/h6-8,14-16H,4-5,9-10H2,1-3H3/t14-,15+,16+

| StdInChIKey = HDDNYFLPWFSBLN-ZSHCYNCHSA-N

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

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| pregnancy_category =

| legal_status =

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}}

Tropanserin (INN; MDL-72,422) is a drug which acts as a potent and selective 5-HT3 receptor antagonist.{{cite book | vauthors = King FD, Jones BJ, Sanger GJ | title = 5-Hydroxytryptamine-3 Receptor Antagonists | url = https://books.google.com/books?id=YSUAQFAga3oC&pg=PA244 | access-date = 6 May 2012 | date = 22 October 1993 | publisher = CRC Press | isbn = 978-0-8493-5463-2 | page = 244}} It was investigated in clinical trials for the treatment of migraine in the 1980s but was never marketed.{{cite book | vauthors = Johnson G | chapter = Recent Advances in Migraine Research | veditors = Bailey DM | title = Annual Reports in Medicinal Chemistry | chapter-url = https://books.google.com/books?id=oJeTSJveeuAC&pg=PA44 | date = 1 August 1987 | volume = 22 | publisher = Academic Press | isbn = 978-0-08-058366-2 | doi = 10.1016/S0065-7743(08)61153-7 | page = 44}}

Synthesis

Tropanserin can be prepared by the reaction of tropine with 3,5-dimethylbenzoyl chloride.

File:Tropanserin synthesis.svg

See also

References

{{Reflist}}

{{Serotonergics}}

Category:5-HT3 antagonists

Category:Benzoate esters

Category:Tropanes

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