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Chemical compound
2β-Propanoyl-3β-(4-tolyl)-tropane
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 )
Formula C 18 H 25 N O
Molar mass 271.404 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 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
^ 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 .
DAT Tooltip Dopamine transporter (
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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)