2β-Propanoyl-3β-(4-tolyl)-tropane

Chemical compound
2β-Propanoyl-3β-(4-tolyl)-tropane
Identifiers
  • 1-[(1R,2S,3S,5S)-8-methyl-3-(4-methylphenyl)-8-azabicyclo[3.2.1]octan-2-yl]propan-1-one
CAS Number
  • 152783-29-4
PubChem CID
  • 127862
ChemSpider
  • 113404
CompTox Dashboard (EPA)
  • DTXSID60934599 Edit this at Wikidata
Chemical and physical data
FormulaC18H25NO
Molar mass271.404 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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

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]

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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DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
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2-Carboxymethyl Esters
(3,4-Disubstituted Phenyl)-tropanes
Arylcarboxy
Carboxyalkyl
Acyl
  • PTT/WF-11
  • WF-23
  • PIT/WF-21
  • WF-33
β,α Stereochemistry
α,β Stereochemistry
Heterocycles: 3-Substituted-isoxazol-5-yl
Heterocycles: 3-Substituted-1,2,4-oxadiazole
N-alkyl
  • FP-β-CPPIT
  • FE-β-CPPIT
  • Altropane
  • Ioflupane (123I)
N-replaced (S,O,C)
Irreversible
Nortropanes (N-demethylated)
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