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Brasofensine

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Brasofensine
File:Brasofensine.gif
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • (E)-1-[(1R,2R,3S,5S)-3-(3,4-dichlorophenyl)-8-methyl-8-azabicyclo[3.2.1]oct-2-yl]-N-methoxymethanimine
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H20Cl2N2O
Molar mass327.249 g/mol g·mol−1
3D model (JSmol)
  • CN3[C@H]1CC[C@@H]3[C@H](\C=N\OC)[C@H](C1)c2ccc(Cl)c(Cl)c2

Brasofensine is a serotonin-noradrenaline-dopamine reuptake inhibitor. It has been researched for the treatment of Parkinson's Disease, depression and treatment of drug dependence. Phase II trials were conducted in 1996 and brasofensine was shown to be both effective and well tolerated at a dose of 4mg,[1] however development was stopped after problems with in vivo cis-anti isomerization of the 2α-methyloxime group.[2]

The isomerization of brasofensine is not between the alpha and beta positions on the 2 position of the tropane ring but rather the E/Z isomerization of the imine (i.e. "methyl-aldoxime").[3]

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Brasofensine is a Class A drug in the UK.[4]

See also

References

  1. ^ Frackiewicz EJ, Jhee SS, Shiovitz TM, Webster J, Topham C, Dockens RC, Whigan D, Salazar DE, Cutler NR. Brasofensine treatment for Parkinson's disease in combination with levodopa/carbidopa. Ann Pharmacother. 2002 Feb;36(2):225-30.
  2. ^ Runyon SP, Carroll FI. Dopamine transporter ligands: recent developments and therapeutic potential. Current Topics in Medicinal Chemistry. 2006;6(17):1825-43. PMID 17017960
  3. ^ [1]
  4. ^ [http://www.homeoffice.gov.uk/documents/cdlist.pdf?view=Binary Misuse of drugs list of drugs currently controlled under the misuse of drugs legislation. UK Home Office August 2008 (listed as 3-(3,4-Dichlorophenyl)-8-Methyl-8-Aza-Bicyclo(3.2.1) Octane-2-Carbaldehyde-0-Methyloxine)]
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