Xorphanol

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IUPAC_name = N-(Cyclobutylmethyl)-8β-methyl-6-methylenemorphinan-3-ol


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CAS_number = 77287-89-9
synonyms = Xorphanol, TR-5379
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PubChem = 5488631
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C = 23 | H = 31 | N = 1 | O = 1
molecular_weight = 337.498 g/mol
smiles = C [C@H] 1CC(=C)C [C@@] 23 [C@@H] 1 [C@@H] (CC4=C2C=C(C=C4)O)N(CC3)CC5CCC5
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Xorphanol (TR-5379) is an opioid analgesic from the morphinan family of drugs. It is a mixed agonist-antagonist at the μ-opioid receptor and produces potent analgesic effects with little potential for dependence or abuse. [Polazzi JO, Kotick MP, Howes JF, Bousquet AR. Analgesic narcotic antagonists. 9. 6-Methylene-8 beta-alkyl-N-(cycloalkylmethyl)-3-hydroxy- or -methoxymorphinans. "Journal of Medicinal Chemistry". 1981 Dec;24(12):1516-8. PMID 6796691] [McCarthy PS, Howlett GJ. Physical dependence induced by opiate partial agonists in the rat. "Neuropeptides". 1984 Dec;5(1-3):11-4. PMID 6152317] [Howes JF, Villarreal JE, Harris LS, Essigmann EM, Cowan A. Xorphanol. "Drug and Alcohol Dependence". 1985 Feb;14(3-4):373-80. PMID 4039650]

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. [Porter MC, Hartnagel RE, Clemens GR, Kowalski RL, Bare JJ, Halliwell WE, Kitchen DN. Preclinical toxicity and teratogenicity studies with the narcotic antagonist analgesic drug TR5379M. "Fundamental and Applied Toxicology". 1983 Sep-Oct;3(5):478-82. PMID 6642105] 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. [ [http://bulk.resource.org/courts.gov/c/F3/13/13.F3d.6.93-1385.html "Maruho Company Ltd v Miles Inc" (1993) 13 F.3d 6] ] This dispute resulted in the drug never being marketed commercially, although it is still used in scientific research.

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