Jump to content

Epiboxidine: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
Importing Wikidata short description: "Chemical compound" (Shortdesc helper)
Restored revision 1105372579 by Ruud Buitelaar (talk): Was fine before, without the sock
 
(5 intermediate revisions by 3 users not shown)
Line 39: Line 39:
== Uses ==
== 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<ref>{{cite journal | vauthors = Yan X, Zhao B, Butt CM, Debski EA | title = Nicotine exposure refines visual map topography through an NMDA receptor-mediated pathway | journal = The European Journal of Neuroscience | volume = 24 | issue = 11 | pages = 3026–42 | date = December 2006 | pmid = 17156364 | doi = 10.1111/j.1460-9568.2006.05204.x | s2cid = 25993659 }}</ref> and as a parent compound to derive newer analogues which may be safer and have greater potential for clinical development.<ref>{{cite journal | vauthors = Fitch RW, Pei XF, Kaneko Y, Gupta T, Shi D, Federova I, Daly JW | title = Homoepiboxidines: further potent agonists for nicotinic receptors | journal = Bioorganic & Medicinal Chemistry | volume = 12 | issue = 1 | pages = 179–90 | date = January 2004 | pmid = 14697783 | doi = 10.1016/j.bmc.2003.10.015 }}</ref><ref>{{cite journal | vauthors = Cheng J, Izenwasser S, Zhang C, Zhang S, Wade D, Trudell ML | title = Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo[3.2.1]octanes | journal = Bioorganic & Medicinal Chemistry Letters | volume = 14 | issue = 7 | pages = 1775–8 | date = April 2004 | pmid = 15026069 | doi = 10.1016/j.bmcl.2004.01.025 }}</ref><ref>{{cite journal | vauthors = Armstrong A, Bhonoah Y, Shanahan SE | title = Aza-Prins-pinacol approach to 7-azabicyclo[2.2.1]heptanes: syntheses of (+/-)-epibatidine and (+/-)-epiboxidine | journal = The Journal of Organic Chemistry | volume = 72 | issue = 21 | pages = 8019–24 | date = October 2007 | pmid = 17867705 | doi = 10.1021/jo701536a }}</ref>
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<ref>{{cite journal | vauthors = Yan X, Zhao B, Butt CM, Debski EA | title = Nicotine exposure refines visual map topography through an NMDA receptor-mediated pathway | journal = The European Journal of Neuroscience | volume = 24 | issue = 11 | pages = 3026–42 | date = December 2006 | pmid = 17156364 | doi = 10.1111/j.1460-9568.2006.05204.x | s2cid = 25993659 }}</ref> and as a parent compound to derive newer analogues which may be safer and have greater potential for clinical development.<ref>{{cite journal |author-link4=Taruna Madan Gupta |vauthors=Fitch RW, Pei XF, Kaneko Y, Gupta T, Shi D, Federova I, Daly JW |date=January 2004 |title=Homoepiboxidines: further potent agonists for nicotinic receptors |journal=Bioorganic & Medicinal Chemistry |volume=12 |issue=1 |pages=179–90 |doi=10.1016/j.bmc.2003.10.015 |pmid=14697783}}</ref><ref>{{cite journal | vauthors = Cheng J, Izenwasser S, Zhang C, Zhang S, Wade D, Trudell ML | title = Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo[3.2.1]octanes | journal = Bioorganic & Medicinal Chemistry Letters | volume = 14 | issue = 7 | pages = 1775–8 | date = April 2004 | pmid = 15026069 | doi = 10.1016/j.bmcl.2004.01.025 }}</ref><ref>{{cite journal | vauthors = Armstrong A, Bhonoah Y, Shanahan SE | title = Aza-Prins-pinacol approach to 7-azabicyclo[2.2.1]heptanes: syntheses of (+/-)-epibatidine and (+/-)-epiboxidine | journal = The Journal of Organic Chemistry | volume = 72 | issue = 21 | pages = 8019–24 | date = October 2007 | pmid = 17867705 | doi = 10.1021/jo701536a }}</ref>


== See also ==
== See also ==

Latest revision as of 10:23, 20 November 2022

Epiboxidine
Legal status
Legal status
  • Investigational
Identifiers
  • (1R,4S,6S)-6-(3-Methylisoxazol-5-yl)-7-azabicyclo[2.2.1]heptane
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H14N2O
Molar mass178.235 g·mol−1
3D model (JSmol)
  • CC1=NOC(=C1)[C@H]2C[C@@H]3CC[C@H]2N3
  • InChI=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
  • Key:GEEFPQBPVBFCSD-XHNCKOQMSA-N

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.[1][2][3]

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[4] and as a parent compound to derive newer analogues which may be safer and have greater potential for clinical development.[5][6][7]

See also

[edit]

References

[edit]
  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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[3.2.1]octanes". Bioorganic & Medicinal Chemistry Letters. 14 (7): 1775–8. doi:10.1016/j.bmcl.2004.01.025. PMID 15026069.
  7. ^ Armstrong A, Bhonoah Y, Shanahan SE (October 2007). "Aza-Prins-pinacol approach to 7-azabicyclo[2.2.1]heptanes: syntheses of (+/-)-epibatidine and (+/-)-epiboxidine". The Journal of Organic Chemistry. 72 (21): 8019–24. doi:10.1021/jo701536a. PMID 17867705.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Epiboxidine&oldid=1122882693"