4-NEMD

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Chemical compound

title: "4-NEMD" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["alpha2-adrenergic-agonists", "imidazoles", "1-naphthyl-compounds", "naphthylethylamines"] description: "Chemical compound" topic_path: "general/alpha2-adrenergic-agonists" source: "https://en.wikipedia.org/wiki/4-NEMD" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477223019 | IUPAC_name = (S)-4-(1-Naphthalen-1-ylethyl)-1H-imidazole | image = 4-NEMD.svg | image_class = skin-invert-image

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | excretion = | CAS_number_Ref = | CAS_number = 156833-39-5 | UNII_Ref = | UNII = H3R6PW4CUC | ATC_prefix = None | ATC_suffix = | ATC_supplemental = | PubChem = 132110 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 24531958

| C = 15 | H = 14 | N = 2 | smiles = CC(C1=CC=CC2=CC=CC=C21)C3=CN=CN3 | StdInChI_Ref = | 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 = | 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. 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, which may have selectivity for the different subtypes of the alpha-2 receptor. It has two isomers, with the (S) isomer being the more potent, as with medetomidine. 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.

References

References

  1. (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.
  2. (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.
  3. (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.
  4. (January 2004). "Medetomidine analogs as selective agonists for the human alpha2-adrenoceptors". Biochemical Pharmacology.
  5. (1992). "Resolution and adrenergic activities of the optical isomers of 4-[1-(1-naphthyl)ethyl]-1H-imidazole". Chirality.
  6. "4-(1-(1-naphthalenyl)ethyl)-1H- imidazole, method of making and use as an anesthetic agent.".

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alpha2-adrenergic-agonistsimidazoles1-naphthyl-compoundsnaphthylethylamines