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| Formula | C10H14N2O |
| Molar mass | 178.235 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 nicotinic 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.
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 and as a parent compound to derive newer analogues which may be safer and "have greater potential for clinical development."
See also※
References※
- ^ Rizzi L, "Dallanoce C," Matera C, Magrone P, Pucci L, Gotti C, et al. (August 2008). "Epiboxidine and novel-related analogues: a convenient synthetic approach and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes" (PDF). Bioorganic & Medicinal Chemistry Letters. 18 (16): 4651–4. doi:10.1016/j.bmcl.2008.07.016. hdl:2434/59291. PMID 18644719.
- ^ Dallanoce C, Matera C, De Amici M, Rizzi L, Pucci L, Gotti C, et al. (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. 24 (7): 543–51. doi:10.1002/chir.22052. PMID 22566097.
- ^ Badio B, Garraffo HM, Plummer CV, Padgett WL, Daly JW (February 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.
- ^ Yan X, Zhao B, Butt CM, Debski EA (December 2006). "Nicotine exposure refines visual map topography through an NMDA receptor-mediated pathway". The European Journal of Neuroscience. 24 (11): 3026–42. doi:10.1111/j.1460-9568.2006.05204.x. PMID 17156364. S2CID 25993659.
- ^ Fitch RW, Pei XF, Kaneko Y, Gupta T, Shi D, Federova I, Daly JW (January 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.
- ^ Cheng J, Izenwasser S, Zhang C, Zhang S, Wade D, Trudell ML (April 2004). "Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo※octanes". Bioorganic & Medicinal Chemistry Letters. 14 (7): 1775–8. doi:10.1016/j.bmcl.2004.01.025. PMID 15026069.
- ^ Armstrong A, Bhonoah Y, Shanahan SE (October 2007). "Aza-Prins-pinacol approach to 7-azabicyclo※heptanes: syntheses of (+/-)-epibatidine and (+/-)-epiboxidine". The Journal of Organic Chemistry. 72 (21): 8019–24. doi:10.1021/jo701536a. PMID 17867705.