4-NEMD

4-NEMD
Identifiers
	IUPAC name 4-(1-Naphthalen-1-ylethyl)-1H-imidazole;
CAS Number	137967-81-8 ;
PubChem CID	132110;
ChemSpider	24531958 ;
CompTox Dashboard (EPA)	DTXSID501237378 ;
Chemical and physical data
Formula	C15H14N2
Molar mass	222.291 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:DZSQSLQSMKNVBV-NSHDSACASA-N ;
	(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.^[6]

References

^ 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 Medicinal Chemistry. 37 (15): 2328–33. doi:10.1021/jm00041a011. PMID 7914537.
^ 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 Medicinal Chemistry. 39 (15): 3001–13. doi:10.1021/jm9506074. PMID 8709134.
^ 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 Medicinal Chemistry. 40 (19): 3014–24. doi:10.1021/jm960642q. PMID 9301663.
^ 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". Biochemical pharmacology. 67 (1): 87–96. doi:10.1016/j.bcp.2003.08.043. PMID 14667931.{{cite journal}}: CS1 maint: numeric names: authors list (link)
^ 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. doi:10.1002/chir.530040706. PMID 1361151.
^ 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.

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[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 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; 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 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; 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 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, 2nd; Miller, DD; Feller, DR (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.{{cite journal}}: CS1 maint: numeric names: authors list (link)

[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. doi:10.1002/chir.530040706. PMID 1361151.

[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.

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