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;
UNII	04B48I6VHR;
CompTox Dashboard (EPA)	DTXSID0042618 ;
Chemical and physical data
Formula	C17H23NO2
Molar mass	273.376 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]

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

[1]
King FD, Jones BJ, Sanger GJ (22 October 1993). 5-Hydroxytryptamine-3 Receptor Antagonists. CRC Press. p. 244. ISBN 978-0-8493-5463-2. Retrieved 6 May 2012.
[2]
Johnson G (1 August 1987). "Recent Advances in Migraine Research". In Bailey DM (ed.). Annual Reports in Medicinal Chemistry. Vol. 22. Academic Press. p. 44. doi:10.1016/S0065-7743(08)61153-7. ISBN 978-0-08-058366-2.
[3]
US 4563465, Fozard JR, Gittos MW, "Treatment of migraine with substituted tropyl benzoate derivatives", issued 7 January 1986, assigned to Merrell Dow Pharma

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Synthesis

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
UNII	04B48I6VHR
CompTox Dashboard (EPA)	DTXSID0042618
Chemical and physical data
Formula	C₁₇H₂₃NO₂
Molar mass	273.376 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