| 词条 | Difluoropine |
| 释义 |
| verifiedrevid = 449575916 | IUPAC_name = methyl (1S,2S,3S,5R)-3-[bis(4-fluorophenyl)methoxy]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate | image = Difluoropine.png | width = 240 | tradename = | routes_of_administration = | CAS_number = 156774-35-5 | ATC_prefix = none | ATC_suffix = | PubChem = 190851 | ChemSpiderID = 165751 | ChEMBL = 1945126 | C=23 | H=25 | F=2 | N=1 | O=3 | molecular_weight = 401.448 | 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 }}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.[1] It is structurally related to benztropine and has similar anticholinergic and antihistamine effects in addition to its dopamine reuptake inhibitory action.[2] 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.[3] It showed promising effects in alleviating the symptoms of Parkinson's Disease in an animal model of the disorder.[4] It is not explicitly illegal anywhere in the world {{as of|2008|lc=on}}, but might be considered to be a 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
References1. ^{{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 | doi=10.1021/jm00039a014}} {{Stimulants}}{{Monoamine reuptake inhibitors}}{{Phenyltropanes}}{{nervous-system-drug-stub}}2. ^{{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 }} 3. ^{{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 }} 4. ^{{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 | last10 = Bonab | first10 = A. A. | last11 = Fischman | first11 = A. J. | 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 | display-authors = 8 }} 5 : Tropanes|Dopamine reuptake inhibitors|Stimulants|Ethers|Fluoroarenes |
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