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2β-Propanoyl-3β-(2-naphthyl)-tropane

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2β-Propanoyl-3β-(2-naphthyl)-tropane
Pharmacokinetic data
Bioavailabilityhigh
Metabolismslow
Identifiers
  • 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)
  • CCC(=O)[C@H]1[C@H]2CC[C@@H](C[C@@H]1c3ccc4ccccc4c3)N2C
  • 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 (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]

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): 1176–1186. 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): 1246–1254. PMID 9618429.
  4. ^ Kimmel HL, Carroll FI, Kuhar MJ (January 2003). "Withdrawal from repeated cocaine alters dopamine transporter protein turnover in the rat striatum". The Journal of Pharmacology and Experimental Therapeutics. 304 (1): 15–21. doi:10.1124/jpet.102.038018. PMID 12490570.
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