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Difluoropine
Systematic (IUPAC) name
methyl (1S,2S,3S,5R)-3-[bis(4-fluorophenyl)methoxy]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Identifiers
CAS number 156774-35-5
ATC code none
PubChem 190851
Chemical data
Formula C 23H25F2NO3  
Mol. mass 401.446
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

(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, 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

References

  1. ^ Meltzer PC, Liang AY, Madras BK. The discovery of an unusually selective and novel cocaine analog: difluoropine. Synthesis and inhibition of binding at cocaine recognition sites. Journal of Medicinal Chemistry. 1994 Jun 24;37(13):2001-10. PMID 8027983
  2. ^ Campbell VC, Kopajtic TA, Newman AH, Katz JL. Assessment of the influence of histaminergic actions on cocaine-like effects of 3alpha-diphenylmethoxytropane analogs. Journal of Pharmacology and Experimental Therapeutics. 2005 Nov;315(2):631-40. PMID 16055673
  3. ^ Katz JL, Izenwasser S, Kline RH, Allen AC, Newman AH. Novel 3alpha-diphenylmethoxytropane analogs: selective dopamine uptake inhibitors with behavioral effects distinct from those of cocaine. Journal of Pharmacology and Experimental Therapeutics. 1999 Jan;288(1):302-15. PMID 9862785
  4. ^ Madras BK, Fahey MA, Goulet M, Lin Z, Bendor J, Goodrich C, Meltzer PC, Elmaleh DR, Livni E, Bonab AA, Fischman AJ. Dopamine transporter (DAT) inhibitors alleviate specific parkinsonian deficits in monkeys: association with DAT occupancy in vivo. Journal of Pharmacology and Experimental Therapeutics. 2006 Nov;319(2):570-85. PMID 16885433
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