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Epiboxidine

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Epiboxidine
Identifiers
  • (1R,4S,6S)-6-(3-methylisoxazol-5-yl)-7-azabicyclo[2.2.1]heptane
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H14N2O
Molar mass178.23 g/mol
3D model (JSmol)
  • CC1=NOC(=C1)[C@H]2C[C@@H]3CC[C@H]2N3

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. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 9063687, please use {{cite journal}} with |pmid=9063687 instead.
  2. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 17156364, please use {{cite journal}} with |pmid=17156364 instead.
  3. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 14697783, please use {{cite journal}} with |pmid=14697783 instead.
  4. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 15026069, please use {{cite journal}} with |pmid=15026069 instead.
  5. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 17867705, please use {{cite journal}} with |pmid=17867705 instead.



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