4-NEMD

{{short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477223019

| IUPAC_name = (S)-4-(1-Naphthalen-1-ylethyl)-1H-imidazole

| image = 4-NEMD.svg

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 156833-39-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = H3R6PW4CUC

| ATC_prefix = None

| ATC_suffix =

| ATC_supplemental =

| PubChem = 132110

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 24531958

| C = 15

| H = 14

| N = 2

| smiles = CC(C1=CC=CC2=CC=CC=C21)C3=CN=CN3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = DZSQSLQSMKNVBV-NSHDSACASA-N

}}

4-NEMD is a potent sedative drug which acts as a selective alpha-2 adrenergic receptor agonist. It is closely related to dexmedetomidine but is several times more potent.{{cite journal | vauthors = Hong SS, Romstedt KJ, Feller DR, Hsu FL, Cupps TL, Lyon RA, Miller DD | title = 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 = Journal of Medicinal Chemistry | volume = 37 | issue = 15 | pages = 2328–33 | date = July 1994 | pmid = 7914537 | doi = 10.1021/jm00041a011 }} 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,{{cite journal | vauthors = Zhang X, Yao XT, Dalton JT, Shams G, Lei L, Patil PN, Feller DR, Hsu FL, George C, Miller DD | display-authors = 6 | title = Medetomidine analogs as alpha 2-adrenergic ligands. 2. Design, synthesis, and biological activity of conformationally restricted naphthalene derivatives of medetomidine | journal = Journal of Medicinal Chemistry | volume = 39 | issue = 15 | pages = 3001–13 | date = July 1996 | pmid = 8709134 | doi = 10.1021/jm9506074 }}{{cite journal | vauthors = Zhang X, De Los Angeles JE, He MY, Dalton JT, Shams G, Lei L, Patil PN, Feller DR, Miller DD, Hsu FL | display-authors = 6 | title = 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 = Journal of Medicinal Chemistry | volume = 40 | issue = 19 | pages = 3014–24 | date = September 1997 | pmid = 9301663 | doi = 10.1021/jm960642q }} which may have selectivity for the different subtypes of the alpha-2 receptor.{{cite journal | vauthors = Lalchandani SG, Zhang X, Hong SS, Liggett SB, Li W, Moore BM, Miller DD, Feller DR | display-authors = 6 | title = Medetomidine analogs as selective agonists for the human alpha2-adrenoceptors | journal = Biochemical Pharmacology | volume = 67 | issue = 1 | pages = 87–96 | date = January 2004 | pmid = 14667931 | doi = 10.1016/j.bcp.2003.08.043 }} It has two isomers, with the (S) isomer being the more potent, as with medetomidine.{{cite journal | vauthors = Hong SS, Romstedt KJ, Feller DR, Hsu FL, George C, Cupps TL, Lyon RA, Miller DD | display-authors = 6 | title = Resolution and adrenergic activities of the optical isomers of 4-[1-(1-naphthyl)ethyl]-1H-imidazole | journal = Chirality | volume = 4 | issue = 7 | pages = 432–8 | year = 1992 | pmid = 1361151 | doi = 10.1002/chir.530040706 }} 4-NEMD was also investigated by the United States military as an anesthetic 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.{{cite patent | url = http://www.google.com/patents?id=MLUiAAAAEBAJ&dq=5151526 | inventor = Hsu FL, Ashman WP | title = 4-(1-(1-naphthalenyl)ethyl)-1H- imidazole, method of making and use as an anesthetic agent. | country = US | number = 5151526 }}