Article · Wikipedia archive · Last revised Aug 6, 2026

2β-Propanoyl-3β-(2-naphthyl)-tropane

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

Last revised
Aug 6, 2026
Read time
≈ 1 min
Length
330 w
Citations
4
Source
Wikipedia ↗
2β-Propanoyl-3β-(2-naphthyl)-tropane
Pharmacokinetic data
BioavailabilityHigh
Elimination half-lifeSlow
Identifiers
  • 1-[(1S,3S,4R,5R)-8-methyl-3-naphthalen-2-yl-8-azabicyclo[3.2.1]octan-4-yl]propan-1-one
CAS Number
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;23 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.

WF-23 is made from methyl-ferruginine i.e. PC10080982 [152668-77-4].

See also

See also

References

References

  1. US 6008227, Davies HM, Childers SR, Bennett B, "Process for blocking 5-HT and dopamine uptake with biologically active tropane derivatives", issued 28 December 1999, assigned to Wake Forest University Health Sciences 
  2. Bennett BA, Wichems CH, Hollingsworth CK, Davies HM, Thornley C, Sexton T, et al. (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. S2CID 27253009.
Further reading

Further reading