4-NEMD

drugbox
IUPAC_name = 4-(1-naphthalen-1-ylethyl)-1H-imidazole


CAS_number = 137967-81-8
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PubChem = 132110
DrugBank =
C=15 | H=14 | N=2
molecular_weight = 222.285 g/mol
smiles = CC(C1=CC=CC2=CC=CC=C21)C3=CN=CN3
bioavailability =
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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. [Hong SS, Romstedt KJ, Feller DR, Hsu FL, Cupps TL, Lyon RA, Miller DD. 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". 1994 Jul 22;37(15):2328-33. PMID 7914537] 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, [Zhang X, Yao XT, Dalton JT, Shams G, Lei L, Patil PN, Feller DR, Hsu FL, George C, Miller DD. Medetomidine analogs as alpha 2-adrenergic ligands. 2. Design, synthesis, and biological activity of conformationally restricted naphthalene derivatives of medetomidine. "Journal of Medicinal Chemistry". 1996 Jul 19;39(15):3001-13. PMID 8709134] [Zhang X, De Los Angeles JE, He MY, Dalton JT, Shams G, Lei L, Patil PN, Feller DR, Miller DD, Hsu FL. 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". 1997 Sep 12;40(19):3014-24. PMID 9301663] which may have selectivity for the different subtypes of the alpha-2 receptor. [Lalchandani SG, Zhang X, Hong SS, Liggett SB, Li W, Moore BM 2nd, Miller DD, Feller DR. Medetomidine analogs as selective agonists for the human alpha2-adrenoceptors. "Biochemical Pharmacology". 2004 Jan 1;67(1):87-96. PMID 14667931] It has two isomers, with the (S) isomer being the more potent, as with medetomidine. [Hong SS, Romstedt KJ, Feller DR, Hsu FL, George C, Cupps TL, Lyon RA, Miller DD. Resolution and adrenergic activities of the optical isomers of 4- [1-(1-naphthyl)ethyl] -1H-imidazole. "Chirality". 1992;4(7):432-8. PMID 1361151] 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. [ [http://www.google.com/patents?id=MLUiAAAAEBAJ&dq=5151526 Fu-Lian Hsu and William P. Ashman. 4-(1-(1-naphthalenyl)ethyl)-1H-imidazole, method of making and use as an anaesthetic agent. US patent 5151526.] ]

References


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