Difluoropine: Difference between revisions

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+{{Short description|Chemical compound}}
 {{Drugbox
-| verifiedrevid = 424712118
+| verifiedrevid = 449575916
-| IUPAC_name = methyl (1S,2S,3S,5R)-3-[bis(4-fluorophenyl)methoxy]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
+| IUPAC_name = methyl (1''S'',2''S'',3''S'',5''R'')-3-[bis(4-fluorophenyl)methoxy]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
-| image = Difluoropine.png
+| image = Difluoropine Structure.svg
-| width = 240
+| width =
 <!--Clinical data-->
 | tradename =
 | routes_of_administration =
 <!--Identifiers-->
@@ Line 14: / Line 15: @@
 | ATC_suffix =
 | PubChem = 190851
+| ChemSpiderID      = 165751
+| ChEMBL = 1945126
 <!--Chemical data-->
 | C=23 | H=25 | F=2 | N=1 | O=3
-| molecular_weight = 401.446
 | smiles = CN1[C@@H]2CC[C@H]1[C@@H]([C@H](C2)OC(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F)C(=O)OC
+| StdInChI          = 1S/C23H25F2NO3/c1-26-18-11-12-19(26)21(23(27)28-2)20(13-18)29-22(14-3-7-16(24)8-4-14)15-5-9-17(25)10-6-15/h3-10,18-22H,11-13H2,1-2H3/t18-,19+,20+,21+/m1/s1
+| StdInChIKey       = XSYGBVSQKPLETJ-ANULTFPQSA-N
+| synonyms = (''S'')-(+)-2β-Carbomethoxy-3α-(bis(4-fluorophenyl)methoxy)tropane
 }}
-'''(S)-(+)-2β-Carbomethoxy-3α-(bis(4-fluorophenyl)methoxy)tropane''' ('''Difluoropine''', '''O-620''') is a [[stimulant]] drug synthesised from [[tropinone]], which acts as a potent and selective [[dopamine reuptake inhibitor]]. Difluoropine is unique among the tropane-derived dopamine reuptake inhibitors in that the active [[stereoisomer]] is the (S) enantiomer rather than the (R) enantiomer, the opposite way round compared to natural [[cocaine]].<ref>{{cite journal | last1 = Meltzer | first1 = PC | last2 = Liang | first2 = AY | last3 = Madras | first3 = BK | title = The discovery of an unusually selective and novel cocaine analog: difluoropine. Synthesis and inhibition of binding at cocaine recognition sites | journal = Journal of medicinal chemistry | volume = 37 | issue = 13 | pages = 2001–10 | year = 1994 | pmid = 8027983 }}</ref> It is structurally related to [[benztropine]] and has similar [[anticholinergic]] and [[antihistamine]] effects in addition to its dopamine reuptake inhibitory action.<ref>{{cite journal | last1 = Campbell | first1 = VC | last2 = Kopajtic | first2 = TA | last3 = Newman | first3 = AH | last4 = Katz | first4 = JL | title = Assessment of the influence of histaminergic actions on cocaine-like effects of 3alpha-diphenylmethoxytropane analogs | journal = The Journal of pharmacology and experimental therapeutics | volume = 315 | issue = 2 | pages = 631–40 | year = 2005 | pmid = 16055673 | doi = 10.1124/jpet.105.090829 }}</ref>
+'''Difluoropine''' ('''O-620''') is a [[stimulant]] drug synthesised from [[tropinone]], which acts as a potent and selective [[dopamine reuptake inhibitor]]. Difluoropine is unique among the tropane-derived dopamine reuptake inhibitors in that the active [[stereoisomer]] is the (S) enantiomer rather than the (R) enantiomer, the opposite way round compared to natural [[cocaine]].<ref>{{cite journal | vauthors = Meltzer PC, Liang AY, Madras BK | title = The discovery of an unusually selective and novel cocaine analog: difluoropine. Synthesis and inhibition of binding at cocaine recognition sites | journal = Journal of Medicinal Chemistry | volume = 37 | issue = 13 | pages = 2001–10 | date = June 1994 | pmid = 8027983 | doi = 10.1021/jm00039a014 }}</ref> It is structurally related to [[benztropine]] and has similar [[anticholinergic]] and [[antihistamine]] effects in addition to its dopamine reuptake inhibitory action.<ref>{{cite journal | vauthors = Campbell VC, Kopajtic TA, Newman AH, Katz JL | title = Assessment of the influence of histaminergic actions on cocaine-like effects of 3alpha-diphenylmethoxytropane analogs | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 315 | issue = 2 | pages = 631–40 | date = November 2005 | pmid = 16055673 | doi = 10.1124/jpet.105.090829 | s2cid = 40671768 }}</ref>
-Difluoropine has some stimulant effects in animals, although it is significantly less powerful than many of the potent [[phenyltropane]] derived stimulant drugs such as [[WIN 35,428]] and [[RTI-55]].<ref>{{cite journal | last1 = Katz | first1 = JL | last2 = Izenwasser | first2 = S | last3 = Kline | first3 = RH | last4 = Allen | first4 = AC | last5 = Newman | first5 = AH | title = Novel 3alpha-diphenylmethoxytropane analogs: selective dopamine uptake inhibitors with behavioral effects distinct from those of cocaine | journal = The Journal of pharmacology and experimental therapeutics | volume = 288 | issue = 1 | pages = 302–15 | year = 1999 | pmid = 9862785 }}</ref> It showed promising effects in alleviating the symptoms of [[Parkinson's Disease]] in an animal model of the disorder.<ref>{{cite journal | last1 = Madras | first1 = BK | last2 = Fahey | first2 = MA | last3 = Goulet | first3 = M | last4 = Lin | first4 = Z | last5 = Bendor | first5 = J | last6 = Goodrich | first6 = C | last7 = Meltzer | first7 = PC | last8 = Elmaleh | first8 = DR | last9 = Livni | first9 = E | title = Dopamine transporter (DAT) inhibitors alleviate specific parkinsonian deficits in monkeys: association with DAT occupancy in vivo | journal = The Journal of pharmacology and experimental therapeutics | volume = 319 | issue = 2 | pages = 570–85 | year = 2006 | pmid = 16885433 | doi = 10.1124/jpet.106.105312 }}</ref>
+Difluoropine has some stimulant effects in animals, although it is significantly less powerful than many of the potent [[phenyltropane]] derived stimulant drugs such as [[WIN 35,428]] and [[RTI-55]].<ref>{{cite journal | vauthors = Katz JL, Izenwasser S, Kline RH, Allen AC, Newman AH | title = Novel 3alpha-diphenylmethoxytropane analogs: selective dopamine uptake inhibitors with behavioral effects distinct from those of cocaine | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 288 | issue = 1 | pages = 302–15 | date = January 1999 | pmid = 9862785 }}</ref> It showed promising effects in alleviating the symptoms of [[Parkinson's disease]] in an animal model of the disorder.<ref>{{cite journal | vauthors = Madras BK, Fahey MA, Goulet M, Lin Z, Bendor J, Goodrich C, Meltzer PC, Elmaleh DR, Livni E, Bonab AA, Fischman AJ | s2cid = 7523758 | display-authors = 6 | title = Dopamine transporter (DAT) inhibitors alleviate specific parkinsonian deficits in monkeys: association with DAT occupancy in vivo | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 319 | issue = 2 | pages = 570–85 | date = November 2006 | pmid = 16885433 | doi = 10.1124/jpet.106.105312 }}</ref>
-It is not explicitly illegal anywhere in the world {{as of|2008|lc=on}}, but might be considered to be a [[Federal Analog Act|controlled substance analogue]] of cocaine on the grounds of its related chemical structure, in some jurisdictions such as the [[USA]], [[Canada]], [[Australia]] and [[New Zealand]].
+It is not explicitly illegal anywhere in the world {{as of|2008|lc=on}}, but might be considered to be a [[Federal Analog Act|controlled substance analogue]] of cocaine on the grounds of its related chemical structure, in some jurisdictions such as the United States, Canada, Australia and New Zealand.
-==See also==
+== See also ==
 * [[List of cocaine analogues]]
-==References==
+== References ==
 {{reflist}}
 {{Stimulants}}
+{{Monoamine reuptake inhibitors}}
-{{Dopaminergics}}
+{{Phenyltropanes}}
 [[Category:Tropanes]]
 [[Category:Dopamine reuptake inhibitors]]
 [[Category:Stimulants]]
-[[Category:Ethers]]
+[[Category:Diphenylmethanol ethers]]
-[[Category:Organofluorides]]
+[[Category:Bis(4-fluorophenyl)methanes]]
+[[Category:Methyl esters]]
 {{nervous-system-drug-stub}}
-[[de:Difluoropin]]