Xorphanol - Misplaced Pages

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Xorphanol
Clinical data

ATC code	none
Identifiers
IUPAC name N-(Cyclobutylmethyl)- 8β-methyl- 6-methylenemorphinan- 3-ol
CAS Number	77287-89-9
PubChem CID	5488631
UNII	L415991P58
Chemical and physical data
Formula	C₂₃H₃₁NO
Molar mass	337.498 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES C1CC(=C)C231(CC4=C2C=C(C=C4)O)N(CC3)CC5CCC5
(verify)

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.

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. This dispute resulted in the drug never being marketed commercially, although it is still used in scientific research.

References

Polazzi, JO; Kotick, MP; Howes, JF; Bousquet, AR (1981). "Analgesic narcotic antagonists. 9. 6-Methylene-8 beta-alkyl-N-(cycloalkylmethyl)-3-hydroxy- or -methoxymorphinans". Journal of medicinal chemistry. 24 (12): 1516–8. PMID 6796691.
McCarthy, PS; Howlett, GJ (1984). "Physical dependence induced by opiate partial agonists in the rat". Neuropeptides. 5 (1–3): 11–4. PMID 6152317.
Howes, JF; Villarreal, JE; Harris, LS; Essigmann, EM; Cowan, A (1985). "Xorphanol". Drug and alcohol dependence. 14 (3–4): 373–80. PMID 4039650.
Porter, MC; Hartnagel, RE; Clemens, GR; Kowalski, RL; Bare, JJ; Halliwell, WE; Kitchen, DN (1983). "Preclinical toxicity and teratogenicity studies with the narcotic antagonist analgesic drug TR5379M". Fundamental and applied toxicology : official journal of the Society of Toxicology. 3 (5): 478–82. PMID 6642105.
Maruho Company Ltd v Miles Inc (1993) 13 F.3d 6