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Eclanamine

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Eclanamine
File:Eclanamine.png
Systematic (IUPAC) name
N-(3,4-dichlorophenyl)-N-[(1R,2R)-2-(dimethylamino)cyclopentyl]propanamide
Clinical data
Identifiers
71027-14-0
67450-45-7 (maleate)
None
PubChem CID 130380
ChemSpider 115358
UNII 5Y67H9W4KQ 7pxY
Chemical data
Formula C16H22Cl2N2O
329.26 g/mol

Eclanamine (U-48,753) is a drug which was patented as an antidepressant, but was never marketed.[1] It acts by inhibiting the reuptake of serotonin and norepinephrine.[2] Eclanamine was discovered by accident as a derivative of the κ-opioid receptor agonist U-50,488.[2]

Synthesis

Some alicyclic 1,2-diamine derivatives have recently been shown to have interesting CNS properties. For example, eclanamine (5) is an antidepressant with a rapid onset of action. The reasons for its potency are not as yet clear but pharmacologists note that the drug desensitizes adrenergic alpha-2 receptors and antagonizes the actions of clonidine.

File:Eclanamine synthesis.svg
Eclanamine synthesis: J. Szmuszkovicz, U.S. Patent 4,159,340 (1979) U.S. Patent 4,156,015 (1979)

The synthesis of eclanamine starts with attack of cyclopentene oxide (1) by dimethylamine (to give 2). This product is converted to the mesylate by reaction with sodium hydride followed by mesyl chloride. Attack of the product (3) by 3,4-dichloroaniline leads to trans-diamine 4. The stereochemical outcome represents a double rear side displacement. The synthesis is completed by acylation with propionic anhydride to give eclanamine (5),[3][4]

See also

References

  1. ^ David J. Triggle (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9. 
  2. ^ a b Progress in Medicinal Chemistry : Volume 29. Elsevier Science Pub Co. 1992. ISBN 0-444-89472-1. 
  3. ^ J. Szmuszkovicz, U.S. Patent 4,159,340 (1979)
  4. ^ U.S. Patent 4,156,015 (1979)