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Epiboxidine

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Epiboxidine
Systematic (IUPAC) name
(1R,4S,6S)-6-(3-methylisoxazol-5-yl)-7-azabicyclo[2.2.1]heptane
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 188895-96-7
ATC code  ?
PubChem CID 5747670
ChemSpider 4677635
Chemical data
Formula C10H14N2O
Mol. mass 178.23 g/mol
SMILES eMolecules & PubChem

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]

Uses

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]

References

  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.  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, 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.  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



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