Oxilorphan

Chemical compound From Wikipedia, the free encyclopedia

Oxilorphan (INN, USAN) (developmental code name L-BC-2605) is an opioid antagonist of the morphinan family that was never marketed.[1] It acts as a μ-opioid receptor (MOR) antagonist but a κ-opioid receptor (KOR) partial agonist, and has similar effects to naloxone and around the same potency as an MOR antagonist.[2] Oxilorphan has some weak partial agonist actions at the MOR (with miosis, nausea, dizziness, and some euphoria observed)[3][4] and can produce hallucinogenic/dissociative effects at sufficient doses, indicative of KOR activation.[5] It was trialed for the treatment of opioid addiction, but was not developed commercially.[6] The KOR agonist effects of oxilorphan are associated with dysphoria, which combined with its hallucinogenic effects, serve to limit its clinical usefulness; indeed, many patients who experienced these side effects refused to take additional doses in clinical trials.[7] It has been encountered as a novel designer drug.[8]

ATC code
  • None
Quick facts Clinical data, ATC code ...
Oxilorphan
Clinical data
ATC code
  • None
Identifiers
  • (-)-17-(Cyclopropylmethyl)-morphinan-3,14-diol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.050.664 Edit this at Wikidata
Chemical and physical data
FormulaC20H27NO2
Molar mass313.441 g·mol−1
3D model (JSmol)
  • Oc3ccc4C[C@H]1N(CC[C@@]2(CCCC[C@@]12O)c4c3)CC5CC5
  • InChI=1S/C20H27NO2/c22-16-6-5-15-11-18-20(23)8-2-1-7-19(20,17(15)12-16)9-10-21(18)13-14-3-4-14/h5-6,12,14,18,22-23H,1-4,7-11,13H2/t18-,19+,20-/m1/s1 checkY
  • Key:STBZIDOIKQNFCQ-HSALFYBXSA-N checkY
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