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8-Carboxamidocyclazocine

Opioid agonist drug

Opioid agonist drug

8-Carboxamidocyclazocine (8-CAC) is an opioid analgesic drug related to cyclazocine, discovered by medicinal chemist Mark P. Wentland and co-workers in Cogswell Laboratory at Rensselaer Polytechnic Institute. Similarly to cyclazocine, 8-CAC acts as an agonist at both the μ- and κ-opioid receptors, but has a much longer duration of action than cyclazocine, and does not have μ antagonist activity. Unexpectedly, it was discovered that the phenolic hydroxyl group of cyclazocine could be replaced by a carboxamido group with only slight loss of potency at opioid receptors, and this discovery has subsequently been used to develop many novel opioid derivatives where the phenolic hydroxy group has been replaced by either carboxamide or a variety of larger groups. Due to their strong κ-opioid agonist activity, these drugs are not suited for use as analgesics in humans, but have instead been researched as potential drugs for the treatment of cocaine addiction.

References

References

  1. US Patent 6784187 8-carboxamido-2,6-methano-3-benzazocines
  2. (March 2001). "8-Carboxamidocyclazocine analogues: redefining the structure-activity relationships of 2,6-methano-3-benzazocines". Bioorganic & Medicinal Chemistry Letters.
  3. (July 2002). "8-Carboxamidocyclazocine: a long-acting, novel benzomorphan". The Journal of Pharmacology and Experimental Therapeutics.
  4. (December 2004). "Effects of the mixed-action kappa/mu opioid agonist 8-carboxamidocyclazocine on cocaine- and food-maintained responding in rhesus monkeys". European Journal of Pharmacology.
  5. (September 2006). "Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. 4. Opioid receptor binding properties of 8-[N-(4'-phenyl)-phenethyl)carboxamido] analogues of cyclazocine and ethylketocycalzocine". Journal of Medicinal Chemistry.
  6. (December 2007). "Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. 5. Opioid receptor binding properties of N-((4'-phenyl)-phenethyl) analogues of 8-CAC". Bioorganic & Medicinal Chemistry Letters.
  7. (May 2008). "Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 6: Opioid receptor binding properties of cyclic variants of 8-carboxamidocyclazocine". Bioorganic & Medicinal Chemistry.
  8. (January 2009). "Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 7: syntheses and opioid receptor properties of cyclic variants of cyclazocine". Bioorganic & Medicinal Chemistry Letters.
  9. (April 2009). "Syntheses of novel high affinity ligands for opioid receptors". Bioorganic & Medicinal Chemistry Letters.
  10. (October 2005). "Kappa opioids as potential treatments for stimulant dependence". The AAPS Journal.
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synthetic-opioids benzomorphans kappa-opioid-receptor-agonists mu-opioid-receptor-agonists carboxamides
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