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4-NEMD

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
4-NEMD
Clinical data
ATC code
  • None
Identifiers
  • (S)-4-(1-Naphthalen-1-ylethyl)-1H-imidazole
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC15H14N2
Molar mass222.291 g·mol−1
3D model (JSmol)
  • CC(C1=CC=CC2=CC=CC=C21)C3=CN=CN3
  • 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 potentsedative drug which acts as a selectivealpha-2 adrenergic receptoragonist. It is closely related todexmedetomidine but is several times more potent.[1] Like other alpha-2 agonists, it produces sedative andmuscle relaxant effects but without producingrespiratory 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 withmedetomidine.[5] 4-NEMD was also investigated by the United States military as ananesthetic 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

[edit]
  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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