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
Bioavailability	High[medical citation needed]
Elimination half-life	Slow[medical citation needed]
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
CAS Number	146877-60-3 Y
PubChem CID	10447943
ChemSpider	8623360
Chemical and physical data
Formula	C21H25NO
Molar mass	307.437 g·mol−1
3D model (JSmol)	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

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

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