4-NEMD

4-NEMD

4-NEMD
Systematic (IUPAC) name
4-(1-Naphthalen-1-ylethyl)-1H-imidazole
Clinical data
Legal status
?
Identifiers
CAS number  N
ATC code ?
PubChem
ChemSpider  YesY
Chemical data
Formula C15H14N2 
Mol. mass 222.285 g/mol
 N   

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.[6]

References

  1. ^ Hong, SS; Romstedt, KJ; Feller, DR; Hsu, FL; Cupps, TL; Lyon, RA; Miller, DD (1994). "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 Medical Chemistry 37 (15): 2328–33.  
  2. ^ Zhang, X; Yao, XT; Dalton, JT; Shams, G; Lei, L; Patil, PN; Feller, DR; Hsu, FL; George, C; Miller, DD (1996). "Medetomidine analogs as alpha 2-adrenergic ligands. 2. Design, synthesis, and biological activity of conformationally restricted naphthalene derivatives of medetomidine". Journal of Medical Chemistry 39 (15): 3001–13.  
  3. ^ Zhang, X; De Los Angeles, JE; He, MY; Dalton, JT; Shams, G; Lei, L; Patil, PN; Feller, DR; Miller, DD; Hsu, FL (1997). "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 Medical Chemistry 40 (19): 3014–24.  
  4. ^ Lalchandani, SG; Zhang, X; Hong, SS; Liggett, SB; Li, W; Moore Bm, 2nd; Miller, DD; Feller, DR (2004). "Medetomidine analogs as selective agonists for the human alpha2-adrenoceptors".  
  5. ^ Hong, SS; Romstedt, KJ; Feller, DR; Hsu, FL; George, C; Cupps, TL; Lyon, RA; Miller, DD (1992). "Resolution and adrenergic activities of the optical isomers of 4-1-(1-naphthyl)ethyl-1H-imidazole". Chirality 4 (7): 432–8.  
  6. ^ Fu-Lian Hsu and William P. Ashman. 4-(1-(1-naphthalenyl)ethyl)- 1H- imidazole, method of making and use as an anesthetic agent. US patent 5151526.