Difluoropine

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Difluoropine
Difluoropine.png
Systematic (IUPAC) name
methyl (1S,2S,3S,5R)-3-[bis(4-fluorophenyl)methoxy]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Clinical data
Legal status ?
Identifiers
CAS number 156774-35-5
ATC code None
PubChem CID 190851
Synonyms (S)-(+)-2β-Carbomethoxy-3α-(bis(4-fluorophenyl)methoxy)tropane
Chemical data
Formula C23H25F2NO3 
Mol. mass 401.448
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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, 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 USA, Canada, Australia and New Zealand.

See also[edit]

References[edit]

  1. ^ Meltzer, PC; Liang, AY; Madras, BK (1994). "The discovery of an unusually selective and novel cocaine analog: difluoropine. Synthesis and inhibition of binding at cocaine recognition sites". Journal of Medical Chemistry 37 (13): 2001–10. doi:10.1021/jm00039a014. PMID 8027983. 
  2. ^ Campbell, VC; Kopajtic, TA; Newman, AH; Katz, JL (2005). "Assessment of the influence of histaminergic actions on cocaine-like effects of 3alpha-diphenylmethoxytropane analogs". The Journal of Pharmacology and Experimental Therapeutics 315 (2): 631–40. doi:10.1124/jpet.105.090829. PMID 16055673. 
  3. ^ Katz, JL; Izenwasser, S; Kline, RH; Allen, AC; Newman, AH (1999). "Novel 3alpha-diphenylmethoxytropane analogs: selective dopamine uptake inhibitors with behavioral effects distinct from those of cocaine". The Journal of Pharmacology and Experimental Therapeutics 288 (1): 302–15. PMID 9862785. 
  4. ^ Madras, BK; Fahey, MA; Goulet, M; Lin, Z; Bendor, J; Goodrich, C; Meltzer, PC; Elmaleh, DR et al. (2006). "Dopamine transporter (DAT) inhibitors alleviate specific parkinsonian deficits in monkeys: association with DAT occupancy in vivo". The Journal of Pharmacology and Experimental Therapeutics 319 (2): 570–85. doi:10.1124/jpet.106.105312. PMID 16885433.