2β-Propanoyl-3β-(2-naphthyl)-tropane

2β-Propanoyl-3β-(2-naphthyl)-tropane or WF-23 (Wake Forest-23, named after the university where it was first created) is a cocaine analogue. It is several hundred times more potent than cocaine at being a serotonin-norepinephrine-dopamine reuptake inhibitor.[1]

2β-Propanoyl-3β-(2-naphthyl)-tropane
Pharmacokinetic data
Bioavailabilityhigh
Metabolismslow
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
ChemSpider
Chemical and physical data
FormulaC21H25NO
Molar mass307.437 g·mol−1
3D model (JSmol)
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

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] as the half-life of the dopamine transporter in rats was found to be 2-3 days under normal conditions (with agonists, antagonists, and transporter inhibitors altering the half-life),[4] it may be that WF-23 largely or mostly binds to its transporters until they are degraded.

See also

References
  1. U.S. Patent 6,008,227
  2. Bennett BA, Wichems CH, Hollingsworth CK, Davies HM, Thornley C, Sexton T, Childers SR (March 1995). "Novel 2-substituted cocaine analogs: uptake and ligand binding studies at dopamine, serotonin and norepinephrine transport sites in the rat brain". The Journal of Pharmacology and Experimental Therapeutics. 272 (3): 1176–86. PMID 7891330.
  3. Daunais JB, Hart SL, Smith HR, Letchworth SR, Davies HM, Sexton T, et al. (June 1998). "Long-acting blockade of biogenic amine transporters in rat brain by administration of the potent novel tropane 2beta-propanoyl-3beta-(2-Naphthyl)-tropane". The Journal of Pharmacology and Experimental Therapeutics. 285 (3): 1246–54. PMID 9618429.
  4. Kimmel, Heather L.; Carroll, F. Ivy; Kuhar, Michael J. (Jan 2003). "Withdrawal from repeated cocaine alters dopamine transporter protein turnover in the rat striatum". J Pharmacol Exp Ther. 304 (1): 15–21. doi:10.1124/jpet.102.038018. PMID 12490570. Retrieved 14 July 2022.
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