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
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
Molecular 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

References

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  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.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
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