Difluoropine

Chemical compound
  • none
Identifiers
  • methyl (1S,2S,3S,5R)-3-[bis(4-fluorophenyl)methoxy]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number
  • 156774-35-5
PubChem CID
  • 190851
ChemSpider
  • 165751
ChEMBL
  • ChEMBL1945126
CompTox Dashboard (EPA)
  • DTXSID20935527 Edit this at Wikidata
Chemical and physical dataFormulaC23H25F2NO3Molar mass401.454 g·mol−13D model (JSmol)
  • Interactive image
  • 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 (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[update], 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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DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
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See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
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2-Carboxymethyl Esters
(3,4-Disubstituted Phenyl)-tropanes
Arylcarboxy
Carboxyalkyl
Acyl
  • PTT/WF-11
  • WF-23
  • PIT/WF-21
  • WF-33
β,α Stereochemistry
α,β Stereochemistry
Heterocycles: 3-Substituted-isoxazol-5-yl
Heterocycles: 3-Substituted-1,2,4-oxadiazole
N-alkyl
  • FP-β-CPPIT
  • FE-β-CPPIT
  • Altropane
  • Ioflupane (123I)
N-replaced (S,O,C)
Irreversible
Nortropanes (N-demethylated)
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