Chemistry:4-NEMD

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Short description: Chemical compound
4-NEMD
4-NEMD.svg
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC15H14N2
Molar mass222.291 g·mol−1
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

4-NEMD is a potent sedative drug which acts as a selective alpha-2 adrenergic agonist. It is closely related to dexmedetomidine but is several times more potent.[1] Like other alpha-2 agonists, it produces sedative and muscle relaxant effects but without producing respiratory depression. It is not currently used in medicine but has been researched as the basis for a potential new generation of alpha-2 agonist drugs,[2][3] which may have selectivity for the different subtypes of the alpha-2 receptor.[4] It has two isomers, with the (S) isomer being the more potent, as with medetomidine.[5] 4-NEMD was also investigated by the United States military as an anaesthetic agent, most likely for use in surgery but possibly also for use as a non-lethal incapacitating agent, although this has not been officially confirmed.[6]

References

  1. "A structure-activity relationship study of benzylic modifications of 4-[1-(1-naphthyl)ethyl]-1H-imidazoles on alpha 1- and alpha 2-adrenergic receptors". Journal of Medicinal Chemistry 37 (15): 2328–33. July 1994. doi:10.1021/jm00041a011. PMID 7914537. 
  2. "Medetomidine analogs as alpha 2-adrenergic ligands. 2. Design, synthesis, and biological activity of conformationally restricted naphthalene derivatives of medetomidine". Journal of Medicinal Chemistry 39 (15): 3001–13. July 1996. doi:10.1021/jm9506074. PMID 8709134. 
  3. "Medetomidine analogs as alpha 2-adrenergic ligands. 3. Synthesis and biological evaluation of a new series of medetomidine analogs and their potential binding interactions with alpha 2-adrenoceptors involving a "methyl pocket"". Journal of Medicinal Chemistry 40 (19): 3014–24. September 1997. doi:10.1021/jm960642q. PMID 9301663. 
  4. "Medetomidine analogs as selective agonists for the human alpha2-adrenoceptors". Biochemical Pharmacology 67 (1): 87–96. January 2004. doi:10.1016/j.bcp.2003.08.043. PMID 14667931. 
  5. "Resolution and adrenergic activities of the optical isomers of 4-[1-(1-naphthyl)ethyl]-1H-imidazole". Chirality 4 (7): 432–8. 1992. doi:10.1002/chir.530040706. PMID 1361151. 
  6. Hsu FL, Ashman WP, "4-(1-(1-naphthalenyl)ethyl)-1H- imidazole, method of making and use as an anesthetic agent.", US patent 5151526