Epiboxidine

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Epiboxidine
Epiboxidine.png
Systematic (IUPAC) name
(1R,4S,6S)-6-(3-methylisoxazol-5-yl)-7-azabicyclo[2.2.1]heptane
Identifiers
CAS Number 188895-96-7
PubChem CID 5747670
ChemSpider 4677635
Chemical data
Formula C10H14N2O
Molar mass 178.23 g/mol

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 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.[1]

Uses[edit]

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]

See also[edit]

ABT-418

References[edit]

  1. ^ Badio, B.; Garraffo, H. M.; Plummer, C. V.; Padgett, W. L.; Daly, J. W. (1997). "Synthesis and nicotinic activity of epiboxidine: an isoxazole analogue of epibatidine". European Journal of Pharmacology 321 (2): 189–194. doi:10.1016/S0014-2999(96)00939-9. PMID 9063687. 
  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. 
  3. ^ Fitch, R. W.; Pei, X. F.; Kaneko, Y.; Gupta, T.; Shi, D.; Federova, I.; Daly, J. W. (2004). "Homoepiboxidines: further potent agonists for nicotinic receptors". Bioorganic & Medicinal Chemistry 12 (1): 179–190. doi:10.1016/j.bmc.2003.10.015. PMID 14697783. 
  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. 
  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.