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- Q7404462 subject Q7158322.
- Q7404462 subject Q7484882.
- Q7404462 subject Q8388304.
- Q7404462 subject Q8600287.
- Q7404462 subject Q8699468.
- Q7404462 subject Q8873601.
- Q7404462 abstract "Salicylmethylecgonine, (2′-Hydroxycocaine) is a tropane derivative drug which is both a synthetic analogue and a possible active metabolite of cocaine. Its potency in vitro is around 10x that of cocaine, although it is only around three times more potent than cocaine when administered to mice (likely owing to it having a higher LogP: 2.89 than that of cocaine: 2.62) Note however that the compound 2′-Acetoxycocaine would act as a prodrug to Salicylmethylecgonine in humans, and has a more efficient partition coefficient which would act as a delivery system and would circumvent this reason for a loss in potency. Salicylmethylecgonine also shows increased behavioral stimulation compared to cocaine similar to the phenyltropanes. The hydroxy branch renders the molecule a QSAR of a 10-fold increase over cocaine in its binding potency for the dopamine transporter & a 52-fold enhanced affinity for the norepinephrine transporter. It also has a reduced selectivity for the serotonin transporter though only due to its greater increase at NET binding; it's SERT affinity being 4-fold increased compared to cocaine. However, in overall binding affinity (not uptake inhibition) it displaces ligands better across the board than cocaine in all monoamine categories.Study of molecular modeling inferred that, in addition to intramolecular hydrogen bonding between the adjacent 3β-carbonyl and the 2′-OH ortho group of 185d (i.e. salicylmethylecgonine), that intermolecular hydrogen bonding between its hydroxy ortho substituent and the dopamine transporter was also possible; and was rationalized to be due to its nearness of where the nitrogen and oxygen atoms reside in the para-hydroxy of dopamine itself and its own intrinsic relation to DAT whereby that mutual hydroxyl functionality is mediated in both salicylmethylecgonine and dopamine in a similar manner. That is, at serine residue 359 on DAT, as the distance of the hydroxy to the bridge-nitrogen on salicylmethylecgonine is 7.96 Å (close to that of the distance between the p-OH & the NH2 atoms of dopamine, their distance apart being 7.83 Å). Which may play a role in this analogs increased behavioral stimulation over its parent compound cocaine. The meta-hydroxy group of dopamine, by contrast, has a distance of 6.38 Å from its nitrogen and is believed to engage with the 356 residue on DAT.".
- Q7404462 iupacName "methyl (1R,2R,3S,5S)-3-(2-hydroxybenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate".
- Q7404462 pubchem "10519659".
- Q7404462 thumbnail Salicylecgonine.png?width=300.
- Q7404462 wikiPageWikiLink Q2499888.
- Q7404462 wikiPageWikiLink Q407595.
- Q7404462 wikiPageWikiLink Q410271.
- Q7404462 wikiPageWikiLink Q41576.
- Q7404462 wikiPageWikiLink Q420028.
- Q7404462 wikiPageWikiLink Q4596728.
- Q7404462 wikiPageWikiLink Q4637034.
- Q7404462 wikiPageWikiLink Q485014.
- Q7404462 wikiPageWikiLink Q603741.
- Q7404462 wikiPageWikiLink Q6610369.
- Q7404462 wikiPageWikiLink Q7050488.
- Q7404462 wikiPageWikiLink Q7158322.
- Q7404462 wikiPageWikiLink Q7181444.
- Q7404462 wikiPageWikiLink Q7484882.
- Q7404462 wikiPageWikiLink Q766383.
- Q7404462 wikiPageWikiLink Q8388304.
- Q7404462 wikiPageWikiLink Q8600287.
- Q7404462 wikiPageWikiLink Q8699468.
- Q7404462 wikiPageWikiLink Q8873601.
- Q7404462 wikiPageWikiLink Q898797.
- Q7404462 iupacName "methyl -3--8-methyl-8-azabicyclo[3.2.1] octane-2-carboxylate".
- Q7404462 pubchem "10519659".
- Q7404462 type ChemicalSubstance.
- Q7404462 type Drug.
- Q7404462 type ChemicalObject.
- Q7404462 type Thing.
- Q7404462 type Q8386.
- Q7404462 comment "Salicylmethylecgonine, (2′-Hydroxycocaine) is a tropane derivative drug which is both a synthetic analogue and a possible active metabolite of cocaine.".
- Q7404462 label "Salicylmethylecgonine".
- Q7404462 depiction Salicylecgonine.png.