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Difluoropine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Difluoropine
Clinical data
Other names(S)-(+)-2β-Carbomethoxy-3α-(bis(4-fluorophenyl)methoxy)tropane
ATC code
  • none
Identifiers
  • methyl (1S,2S,3S,5R)-3-[bis(4-fluorophenyl)methoxy]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC23H25F2NO3
Molar mass401.454 g·mol−1
3D model (JSmol)
  • 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=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 astimulant drug synthesised fromtropinone, which acts as a potent and selectivedopamine reuptake inhibitor. Difluoropine is unique among the tropane-derived dopamine reuptake inhibitors in that the activestereoisomer is the (S) enantiomer rather than the (R) enantiomer, the opposite way round compared to naturalcocaine.[1] It is structurally related tobenztropine and has similaranticholinergic andantihistamine 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 potentphenyltropane derived stimulant drugs such asWIN 35,428 andRTI-55.[3] It showed promising effects in alleviating the symptoms ofParkinson'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 acontrolled 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

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References

[edit]
  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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2-Carboxymethyl Esters
(3,4-Disubstituted Phenyl)-tropanes
Arylcarboxy
Carboxyalkyl
Acyl
β,α Stereochemistry
α,β Stereochemistry
Heterocycles: 3-Substituted-isoxazol-5-yl
Heterocycles: 3-Substituted-1,2,4-oxadiazole
N-alkyl
N-replaced (S,O,C)
Irreversible
Nortropanes (N-demethylated)
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