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Systematic (IUPAC) name
CAS Number 188895-96-7
PubChem CID 5747670
ChemSpider 4677635
Chemical data
Formula C10H14N2O
Molar mass 178.23 g/mol
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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 produces extremely dangerous toxic side effects.

Epiboxidine is around ten times less potent than 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.[1]


Despite its decreased potency and 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[2] and as a parent compound to derive newer analogues which may be safer and have greater potential for clinical development.[3][4][5]


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  1. Badio, B; Garraffo, HM; Plummer, CV; Padgett, WL; Daly, JW (1997). "Synthesis and nicotinic activity of epiboxidine: an isoxazole analogue of epibatidine". European journal of pharmacology. 321 (2): 189–94. doi:10.1016/S0014-2999(96)00939-9. PMID 9063687.  edit
  2. Yan, X.; Zhao, B.; Butt, C.; Debski, E. (2006). "Nicotine exposure refines visual map topography through an NMDA receptor-mediated pathway". The European journal of neuroscience. 24 (11): 3026–3042. doi:10.1111/j.1460-9568.2006.05204.x. PMID 17156364.  edit
  3. Fitch, RW; Pei, XF; Kaneko, Y; Gupta, T; Shi, D; Federova, I; Daly, JW (2004). "Homoepiboxidines: further potent agonists for nicotinic receptors". Bioorganic & medicinal chemistry. 12 (1): 179–90. doi:10.1016/j.bmc.2003.10.015. PMID 14697783.  edit
  4. Cheng, J.; Izenwasser, S.; Zhang, C.; Zhang, S.; Wade, D.; Trudell, M. (2004). "Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo3.2.1octanes". Bioorganic & medicinal chemistry letters. 14 (7): 1775–1778. doi:10.1016/j.bmcl.2004.01.025. PMID 15026069.  edit
  5. Armstrong, A.; Bhonoah, Y.; Shanahan, S. (2007). "Aza-Prins-pinacol approach to 7-azabicyclo2.2.1heptanes: syntheses of (+/-)-epibatidine and (+/-)-epiboxidine". The Journal of organic chemistry. 72 (21): 8019–8024. doi:10.1021/jo701536a. PMID 17867705.  edit