View source for Epiboxidine

{{Drugbox
| IUPAC_name        = (''1R'',''4S'',''6S'')-6-(3-methylisoxazol-5-yl)-7-azabicyclo[2.2.1]heptane
| image             = Epiboxidine.png
| CAS_number        = 188895-96-7
| ATC_prefix        = 
| ATC_suffix        = 
| PubChem           = 5747670
| ChemSpiderID      = 4677635
| chemical_formula  = C<sub>10</sub>H<sub>14</sub>N<sub>2</sub>O
| molecular_weight  = 178.23 g/mol
| smiles            = CC1=NOC(=C1)[C@H]2C[C@@H]3CC[C@H]2N3
| bioavailability   = 
| protein_bound     = 
| metabolism        = 
| elimination_half-life = 
| excretion         = 
| pregnancy_category= 
| legal_status      = 
| routes_of_administration = 
}}

'''Epiboxidine''' is a chemical compound which acts as a [[partial agonist]] at neural [[nicotinic acetylcholine receptor]]s, binding to both the [[ganglion type nicotinic receptor|α3β4]] and the [[Alpha-4 beta-2 nicotinic receptor|α4β2]] [[nicotinic acetylcholine receptor#Subunits|subtypes]]. It was developed as a less toxic [[analog (chemistry)|analogue]] of the potent frog-derived [[alkaloid]] [[epibatidine]], which is around 200 times stronger than [[morphine]] as an [[analgesic]] but produces extremely dangerous toxic [[adverse reaction|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.<ref>{{Cite pmid|9063687}}</ref>

== 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 pmid|17156364}}</ref> and as a parent compound to derive newer analogues which may be safer and have greater potential for clinical development.<ref>{{Cite pmid|14697783}}</ref><ref>{{Cite pmid|15026069}}</ref><ref>{{Cite pmid|17867705}}</ref>

== References ==
{{Reflist|2}}


{{Stimulants}}
{{Analgesics}}
{{Cholinergics}}



[[Category:Analgesics]]
[[Category:Nicotinic agonists]]
[[Category:Stimulants]]
[[Category:Isoxazoles]]


{{analgesic-stub}}

[[es:Epiboxidina]]
[[Category:2Fix]]