Tropanserin

Tropanserin
Clinical data
ATC code	None;
Identifiers
	IUPAC name [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3,5-dimethylbenzoate;
CAS Number	85181-40-4 ; 85181-38-0 (HCl);
PubChem CID	68600;
ChemSpider	19969918;
Chemical and physical data
Formula	C17H23NO2
Molar mass	273.370 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN3[C@H]1CC[C@@H]3C[C@@H](C1)OC(=O)c2cc(C)cc(C)c2;
	InChI InChI=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+; Key:HDDNYFLPWFSBLN-ZSHCYNCHSA-N;

Tropanserin (INN; MDL-72,422) is a drug which acts as a potent and selective 5-HT₃ receptor antagonist.[1] It was investigated in clinical trials for the treatment of migraine in the 1980s but was never marketed.[2]

Synthesis

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

Tropanserin synthesis[3]

Frank D. King; Brian John Jones; Gareth J. Sanger (22 October 1993). 5-Hydroxytryptamine-3 Receptor Antagonists. CRC Press. p. 244. ISBN 978-0-8493-5463-2. Retrieved 6 May 2012.
Denis M. Bailey (1 August 1987). Annual Reports in Medicinal Chemistry. Academic Press. p. 44. ISBN 978-0-12-040522-0. Retrieved 6 May 2012.
J. R. Fozard and M. W. Gittos, U.S. Patent 4,563,465 (1986) via Chem. Abstr., 105:54,608j(1986)

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