Difluoropine

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
Clinical data
Other names(S)-(+)-2β-Carbomethoxy-3α-(bis(4-fluorophenyl)methoxy)tropane
ATC code
  • none
Identifiers
IUPAC name
  • methyl (1S,2S,3S,5R)-3-[bis(4-fluorophenyl)methoxy]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H25F2NO3
Molar mass401.448 g·mol−1
3D model (JSmol)
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
InChI
  • InChI=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
  • Key:XSYGBVSQKPLETJ-ANULTFPQSA-N
  (verify)

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 United States, Canada, Australia and New Zealand.

See also

References
  1. Meltzer PC, Liang AY, Madras BK (June 1994). "The discovery of an unusually selective and novel cocaine analog: difluoropine. Synthesis and inhibition of binding at cocaine recognition sites". Journal of Medicinal Chemistry. 37 (13): 2001–10. doi:10.1021/jm00039a014. PMID 8027983.
  2. Campbell VC, Kopajtic TA, Newman AH, Katz JL (November 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. S2CID 40671768.
  3. Katz JL, Izenwasser S, Kline RH, Allen AC, Newman AH (January 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, et al. (November 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. S2CID 7523758.
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