2β-Propanoyl-3β-(4-tolyl)-tropane

2β-Propanoyl-3β-(4-tolyl)tropane also known as WF-11 or 2-PTT is a cocaine analogue 20 times more potent than cocaine at binding to the dopamine transporter with increased selectivity for the norepinephrine transporters. It also shows marked increase in metabolic stability. In contrast to the findings of cocaine effects, WF-11 has been shown to produce a uniform downregulation of tyrosine hydroxylase protein and activity gene expression with a regimen of use.[1]

2β-Propanoyl-3β-(4-tolyl)-tropane
Identifiers
IUPAC name
  • 1-[(1R,2S,3S,5S)-8-methyl-3-(4-methylphenyl)-8-azabicyclo[3.2.1]octan-2-yl]propan-1-one
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H25NO
Molar mass271.404 g·mol−1
3D model (JSmol)
SMILES
  • CCC(=O)[C@@H]1[C@H]2CC[C@H](N2C)C[C@@H]1C3=CC=C(C=C3)C
InChI
  • InChI=1S/C18H25NO/c1-4-17(20)18-15(13-7-5-12(2)6-8-13)11-14-9-10-16(18)19(14)3/h5-8,14-16,18H,4,9-11H2,1-3H3/t14-,15+,16+,18-/m0/s1
  • Key:PZEAJTAVRYLBTK-LHHMISFZSA-N

See also

References
  1. Freeman WM, Yohrling GJ, Daunais JB, Gioia L, Hart SL, Porrino LJ, et al. (December 2000). "A cocaine analog, 2beta-propanoyl-3beta-(4-tolyl)-tropane (PTT), reduces tyrosine hydroxylase in the mesolimbic dopamine pathway". Drug and Alcohol Dependence. 61 (1): 15–21. doi:10.1016/S0376-8716(00)00119-8. PMID 11064180.
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