Xorphanol

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Opioid analgesic

title: "Xorphanol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["analgesics", "convulsants", "delta-opioid-receptor-agonists", "designer-drugs", "hallucinogenic-kappa-opioid-receptor-agonists", "morphinans", "hydroxyarenes", "semisynthetic-opioids", "cyclobutyl-compounds", "abandoned-drugs"] description: "Opioid analgesic" topic_path: "arts/music" source: "https://en.wikipedia.org/wiki/Xorphanol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Opioid analgesic ::

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| CAS_number_Ref = | CAS_number = 77287-89-9 | ATC_prefix = none | ATC_suffix = | PubChem = 5488631 | DrugBank_Ref = | DrugBank = | UNII_Ref = | UNII = L415991P58 | ChemSpiderID_Ref = | ChemSpiderID = 20121496

| C=23 | H=31 | N=1 | O=1 | smiles = C[C@H]1CC(=C)C[C@@]23[C@@H]1C@@HN(CC3)CC5CCC5 | StdInChI_Ref = | StdInChI = 1S/C23H31NO/c1-15-10-16(2)22-21-11-18-6-7-19(25)12-20(18)23(22,13-15)8-9-24(21)14-17-4-3-5-17/h6-7,12,16-17,21-22,25H,1,3-5,8-11,13-14H2,2H3/t16-,21+,22-,23+/m0/s1 | StdInChIKey_Ref = | StdInChIKey = AZJPPZHRNFQRRE-AZIXLERZSA-N

Xorphanol (INN; also known as xorphanol mesylate (USAN); developmental codes TR-5379 or TR-5379M) is an opioid analgesic of the morphinan family that was never marketed.

Xorphanol is a mixed agonist–antagonist of opioid receptors, acting preferentially as a high-efficacy partial agonist/near-full agonist of the κ-opioid receptor (Ki = 0.4 nM; EC50 = 3.3 nM; Imax = 49%; IA = 0.84) and to a lesser extent as a partial agonist of the μ-opioid receptor (Ki = 0.25 nM; IC50 = 3.4 nM; Imax = 29%) with lower relative intrinsic activity and marked antagonistic potential (including the ability to antagonize morphine-induced effects and induce opioid withdrawal in opioid-dependent individuals). The drug has also been found to act as an agonist of the δ-opioid receptor (Ki = 1.0 nM; IC50 = 8 nM; Imax = 76%).

Xorphanol produces potent analgesia, and was originally claimed to possess a minimal potential for dependence or abuse. Moreover, side effects in animal studies were relatively mild, with only sedation and nausea being prominent, although it also produced convulsions at the highest dose tested. However, human trials revealed additional side effects such as headaches and euphoria, and this was the subject of a lawsuit between the drug's inventors and the company to which they had licensed the marketing rights, which claimed that these side effects had not been revealed to them during the license negotiations. As a result of this dispute, the drug was never marketed commercially.

It has been encountered as a novel designer drug.

References

References

  1. (31 October 1999). "Concise Dictionary of Pharmacological Agents: Properties and Synonyms". Springer Science & Business Media.
  2. (January 1990). "Analgesics". Academic Press.
  3. Lednicer, Daniel. (25 June 1990). "The Organic Chemistry of Drug Synthesis". Wiley.
  4. (1 January 1988). "Neural Mechanisms and Biological Significance of Grooming Behavior". New York Academy of Sciences.
  5. (1988). "Role of opioid receptors in bombesin-induced grooming". Annals of the New York Academy of Sciences.
  6. (1986). "Central infusion of rats with agents selective for different types of opioid receptor". NIDA Research Monograph.
  7. (January 2006). "Pharmacological profiles of opioid ligands at kappa opioid receptors". BMC Pharmacology.
  8. Bernard Testa. (22 October 2013). "Advances in Drug Research". Elsevier.
  9. (January 2003). "Activity of opioid ligands in cells expressing cloned mu opioid receptors". BMC Pharmacology.
  10. Dr. S. S. Kadam. (1 July 2007). "PRINCIPLES OF MEDICINAL CHEMISTRY Vol. - II". Pragati Books Pvt. Ltd..
  11. (November 2002). "Activation profiles of opioid ligands in HEK cells expressing delta opioid receptors". BMC Neuroscience.
  12. (December 1981). "Analgesic narcotic antagonists. 9. 6-Methylene-8 beta-alkyl-N-(cycloalkylmethyl)-3-hydroxy- or -methoxymorphinans". Journal of Medicinal Chemistry.
  13. (December 1984). "Physical dependence induced by opiate partial agonists in the rat". Neuropeptides.
  14. (February 1985). "Xorphanol". Drug and Alcohol Dependence.
  15. (1983). "Preclinical toxicity and teratogenicity studies with the narcotic antagonist analgesic drug TR5379M". Fundamental and Applied Toxicology.
  16. "''Maruho Company Ltd v Miles Inc'' (1993) 13 F.3d 6".
  17. "Ксорфанол (Xorphanol)".

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analgesicsconvulsantsdelta-opioid-receptor-agonistsdesigner-drugshallucinogenic-kappa-opioid-receptor-agonistsmorphinanshydroxyarenessemisynthetic-opioidscyclobutyl-compoundsabandoned-drugs