Epiboxidine

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Chemical compound

title: "Epiboxidine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["analgesics", "nicotinic-agonists", "stimulants", "isoxazoles", "nitrogen-heterocycles"] description: "Chemical compound" topic_path: "general/analgesics" source: "https://en.wikipedia.org/wiki/Epiboxidine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| IUPAC_name = (1R,4S,6S)-6-(3-Methylisoxazol-5-yl)-7-azabicyclo[2.2.1]heptane | image = Epiboxidine skeletal.svg | image_class = skin-invert-image

| tradename = | pregnancy_category = | legal_status = Investigational | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number = 188895-96-7 | UNII_Ref = | UNII = XI646L2ARJ | ATC_prefix = | ATC_suffix = | PubChem = 5747670 | ChemSpiderID = 4677635 | StdInChI = 1S/C10H14N2O/c1-6-4-10(13-12-6)8-5-7-2-3-9(8)11-7/h4,7-9,11H,2-3,5H2,1H3/t7-,8-,9+/m0/s1 | StdInChIKey = GEEFPQBPVBFCSD-XHNCKOQMSA-N

| C=10 | H=14 | N=2 | O=1 | smiles = CC1=NOC(=C1)[C@H]2C[C@@H]3CC[C@H]2N3

Epiboxidine is a chemical compound which acts as a partial agonist at neural nicotinic acetylcholine receptors, binding to both the α3β4 and the α4β2 subtypes. It was developed as a less toxic analogue of the potent frog-derived alkaloid epibatidine, which is around 200 times stronger than morphine as an analgesic but is deadly toxic.

Epiboxidine is around one-tenth as potent as epibatidine as an α4β2 agonist, but has around the same potency as an α3β4 agonist. It has only one-tenth of the analgesic power of epibatidine, but is also much less toxic.

Uses

Despite reduced toxicity compared to epibatidine, epiboxidine itself is still too toxic to be developed as a drug for use in humans. It is used in scientific research and as a parent compound to derive newer analogues which may be safer and have greater potential for clinical development.

References

References

  1. (August 2008). "Epiboxidine and novel-related analogues: a convenient synthetic approach and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes". Bioorganic & Medicinal Chemistry Letters.
  2. (July 2012). "The enantiomers of epiboxidine and of two related analogs: synthesis and estimation of their binding affinity at α4β2 and α7 neuronal nicotinic acetylcholine receptors". Chirality.
  3. (February 1997). "Synthesis and nicotinic activity of epiboxidine: an isoxazole analogue of epibatidine". European Journal of Pharmacology.
  4. (December 2006). "Nicotine exposure refines visual map topography through an NMDA receptor-mediated pathway". The European Journal of Neuroscience.
  5. (January 2004). "Homoepiboxidines: further potent agonists for nicotinic receptors". Bioorganic & Medicinal Chemistry.
  6. (April 2004). "Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo[3.2.1]octanes". Bioorganic & Medicinal Chemistry Letters.
  7. (October 2007). "Aza-Prins-pinacol approach to 7-azabicyclo[2.2.1]heptanes: syntheses of (+/-)-epibatidine and (+/-)-epiboxidine". The Journal of Organic Chemistry.

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analgesicsnicotinic-agonistsstimulantsisoxazolesnitrogen-heterocycles