2β-Propanoyl-3β-(2-naphthyl)-tropane

2β-Propanoyl-3β-(2-naphthyl)-tropane

Pharmacokinetic data
Bioavailability	high
Metabolism	slow
Identifiers
IUPAC name 1-[(1S,3S,4R,5R)-8-methyl-3-naphthalen-2-yl-8-azabicyclo[3.2.1]octan-4-yl]propan-1-one
PubChem (CID)	10447943
ChemSpider	8623360
Chemical and physical data
Formula	C21H25NO
Molar mass	307.43 g/mol
3D model (Jmol)	Interactive image
SMILES CCC(=O)[C@H]1[C@H]2CC[C@@H](C[C@@H]1c3ccc4ccccc4c3)N2C
InChI InChI=1S/C21H25NO/c1-3-20(23)21-18(13-17-10-11-19(21)22(17)2)16-9-8-14-6-4-5-7-15(14)12-16/h4-9,12,17-19,21H,3,10-11,13H2,1-2H3/t17-,18+,19+,21+/m0/s1 Key:WJVLEIDMFWNIAA-QEUVDIPISA-N

2β-Propanoyl-3β-(2-naphthyl)-tropane or WF-23 is a cocaine analogue. It is claimed to be several hundred times more potent than cocaine at being serotonin-norepinephrine-dopamine reuptake inhibitor.^[1]

As can be seen on pubmed, these acyl substituted phenyltropanes are highly potent MAT inhibitors and also have a very long half-life, spanning perhaps at least a few days.^{[2] [3]}

See also

• HDEP-28
• HDMP-28
• List of cocaine analogues

External links

• (Satendra Singh, 2000) Page 16-17

References

1. U.S. Patent 6,008,227
2. Bennett, B. A.; Wichems, C. H.; Hollingsworth, C. K.; Davies, H. M.; Thornley, C.; Sexton, T.; Childers, S. R. (1 March 1995). "Novel 2-substituted cocaine analogs: uptake and ligand binding studies at dopamine, serotonin and norepinephrine transport sites in the rat brain.". Journal of Pharmacology and Experimental Therapeutics. 272 (3): 1176–1186. PMID 7891330.
3. Daunais, J. B.; Hart, S. L.; Smith, H. R.; Letchworth, S. R.; Davies, H. M. L.; Sexton, T.; Bennett, B. A.; Childers, S. R.; Porrino, L. J. (1 June 1998). "Long-Acting Blockade of Biogenic Amine Transporters in Rat Brain by Administration of the Potent Novel Tropane 2β-Propanoyl-3β-(2-Naphthyl)-Tropane". Journal of Pharmacology and Experimental Therapeutics. 285 (3): 1246–1254. PMID 9618429.