Structure via PubChem · Public domain (PubChem)
difluoropine
Sign in to saveDifluoropine (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. It is structurally related to benztropine and has similar anticholinergic and antihistamine effects in addition to its dopamine reuptake inhibitory action.
Chemical data
- Formula
- C23H25F2NO3
- Molecular weight
- 401.4 g/mol
- IUPAC name
- methyl (1S,2S,3S,5R)-3-[bis(4-fluorophenyl)methoxy]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
- 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
- InChIKey
- XSYGBVSQKPLETJ-ANULTFPQSA-N
- XLogP
- 4.2
- Polar surface area
- 38.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 401.18025
Show 4 more facts
- chemical formula
- C₂₃H₂₅F₂NO₃
- canonical SMILES
- CN1C2CCC1C(C(C2)OC(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F)C(=O)OC
- isomeric 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
- Commons category
- Difluoropine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
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. It is structurally related to benztropine and has similar anticholinergic and antihistamine effects in addition to its dopamine reuptake inhibitory action.
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. It showed promising effects in alleviating the symptoms of Parkinson's disease in an animal model of the disorder.
Excerpted from Wikipedia’s “difluoropine” article, available under the CC BY-SA 4.0 licence.