Difluoropine
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| 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 |
| Molar mass | 401.448 |
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| (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, 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
- ↑ Meltzer, PC; Liang, AY; Madras, BK (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.
- ↑ Campbell, VC; Kopajtic, TA; Newman, AH; Katz, JL (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.
- ↑ 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.
- ↑ Madras, BK; Fahey, MA; Goulet, M; Lin, Z; Bendor, J; Goodrich, C; Meltzer, PC; Elmaleh, DR; et al. (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.
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