4-NEMD

4-NEMD
Identifiers
IUPAC name
  • (S)-4-(1-Naphthalen-1-ylethyl)-1H-imidazole
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC15H14N2
Molar mass222.291 g·mol−1
3D model (JSmol)
SMILES
  • CC(C1=CC=CC2=CC=CC=C21)C3=CN=CN3
InChI
  • InChI=1S/C15H14N2/c1-11(15-9-16-10-17-15)13-8-4-6-12-5-2-3-7-14(12)13/h2-11H,1H3,(H,16,17)/t11-/m0/s1 checkY
  • Key:DZSQSLQSMKNVBV-NSHDSACASA-N checkY
 ☒NcheckY (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. ↑ Hong SS, Romstedt KJ, Feller DR, Hsu FL, Cupps TL, Lyon RA, Miller DD (July 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 Medicinal Chemistry. 37 (15): 2328–33. doi:10.1021/jm00041a011. PMID 7914537.
  2. ↑ Zhang X, Yao XT, Dalton JT, Shams G, Lei L, Patil PN, et al. (July 1996). "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. doi:10.1021/jm9506074. PMID 8709134.
  3. ↑ Zhang X, De Los Angeles JE, He MY, Dalton JT, Shams G, Lei L, et al. (September 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 Medicinal Chemistry. 40 (19): 3014–24. doi:10.1021/jm960642q. PMID 9301663.
  4. ↑ Lalchandani SG, Zhang X, Hong SS, Liggett SB, Li W, Moore BM, et al. (January 2004). "Medetomidine analogs as selective agonists for the human alpha2-adrenoceptors". Biochemical Pharmacology. 67 (1): 87–96. doi:10.1016/j.bcp.2003.08.043. PMID 14667931.
  5. ↑ Hong SS, Romstedt KJ, Feller DR, Hsu FL, George C, Cupps TL, et al. (1992). "Resolution and adrenergic activities of the optical isomers of 4-[1-(1-naphthyl)ethyl]-1H-imidazole". Chirality. 4 (7): 432–8. doi:10.1002/chir.530040706. PMID 1361151.
  6. ↑ US 5151526, Hsu FL, Ashman WP, "4-(1-(1-naphthalenyl)ethyl)-1H- imidazole, method of making and use as an anesthetic agent."
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