Epiboxidine

Chemical compound From Wikipedia, the free encyclopedia

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 is deadly toxic.

Legal status
  • Investigational
CAS Number
PubChem CID
ChemSpider
Quick facts Legal status, Identifiers ...
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
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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

Despite reduced 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

References

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