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2β-Propanoyl-3β-(4-tolyl)-tropane

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical 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
PubChemCID
ChemSpider
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC18H25NO
Molar mass271.404 g·mol−1
3D model (JSmol)
  • CCC(=O)[C@@H]1[C@H]2CC[C@H](N2C)C[C@@H]1C3=CC=C(C=C3)C
  • 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 asWF-11 or2-PTT is acocaineanalogue 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 uniformdownregulation oftyrosine hydroxylase protein and activitygene expression with a regimen of use.[1]

See also

[edit]

References

[edit]
  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
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2-Carboxymethyl Esters
(3,4-Disubstituted Phenyl)-tropanes
Arylcarboxy
Carboxyalkyl
Acyl
β,α Stereochemistry
α,β Stereochemistry
Heterocycles: 3-Substituted-isoxazol-5-yl
Heterocycles: 3-Substituted-1,2,4-oxadiazole
N-alkyl
N-replaced (S,O,C)
Irreversible
Nortropanes (N-demethylated)
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