4-NEMD

Chemical compound

4-NEMD
Identifiers

IUPAC name (S)-4-(1-Naphthalen-1-ylethyl)-1H-imidazole
CAS Number	156833-39-5^Y
PubChem CID	132110
ChemSpider	24531958^Y
UNII	H3R6PW4CUC
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^Y Key:DZSQSLQSMKNVBV-NSHDSACASA-N^Y
^NY (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

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ US 5151526, Hsu FL, Ashman WP, "4-(1-(1-naphthalenyl)ethyl)-1H- imidazole, method of making and use as an anesthetic agent."

Hypnotics/sedatives (N05C)

GABA_A

Alcohols	2M2B Chloralodol Ethanol (alcohol) Diethylpropanediol Ethchlorvynol Methylpentynol Trichloroethanol
Barbiturates	Allobarbital Amobarbital Aprobarbital Barbital Butabarbital Butobarbital Cyclobarbital Ethallobarbital Heptabarb Hexobarbital Mephobarbital Methohexital Narcobarbital Pentobarbital Phenallymal Phenobarbital Propylbarbital Proxibarbal Reposal Secobarbital Talbutal Thiamylal Thiopental Thiotetrabarbital Vinbarbital Vinylbital
Benzodiazepines	Brotizolam Cinolazepam Climazolam Clonazolam Doxefazepam Estazolam Flubromazolam Flunitrazolam Flunitrazepam Flurazepam Flutoprazepam Lorazepam Loprazolam Lormetazepam Midazolam Nimetazepam Nitemazepam Nitrazepam Nitrazolam Quazepam Temazepam Triazolam
Carbamates	Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate
Imidazoles	Etomidate Metomidate Propoxate
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Capuride Carbromal Ectylurea
Neuroactive steroids	Acebrochol Allopregnanolone Alphadolone Alphaxolone Eltanolone Hydroxydione Minaxolone Progesterone
Nonbenzodiazepines	Eszopiclone Indiplon Lirequinil Necopidem Pazinaclone Saripidem Suproclone Suriclone Zaleplon Zolpidem Zopiclone
Phenols	Propofol
Piperidinediones	Glutethimide Methyprylon Pyrithyldione Piperidione
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Others	Acetophenone Acetylglycinamide chloral hydrate Bromide compounds Lithium bromide Potassium bromide Sodium bromide Centalun Chloral betaine Chloral hydrate Chloralose Clomethiazole Dichloralphenazone Gaboxadol Kavalactones Loreclezole Paraldehyde Petrichloral Sulfonylalkanes Sulfonmethane (sulfonal) Tetronal Trional Triclofos Sesquiterpene Isovaleramide Isovaleric acid Valerenic acid

GABA_B

H₁

Antihistamines	Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Perlapine Pheniramine Promethazine Propiomazine
Antidepressants	Serotonin antagonists and reuptake inhibitors Etoperidone Nefazodone Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.

α₂-Adrenergic

5-HT_2A

Antidepressants	Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.
Others	Niaprazine