Mirfentanil

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Mirfentanil
Mirfentanil.png
Names
IUPAC name
N-[1-(2-phenylethyl)piperidin-4-yl]-N-pyrazin-2-yl-2-furamide
Other names
MS-32, NIH-10647
Identifiers
117523-47-4 YesY
ChemSpider 54703 N
Jmol-3D images Image
MeSH C069209
PubChem 60698
UNII Q2U943H24P YesY
Properties
C22H24N4O2
Molar mass 376.45156 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

Mirfentanil is a fentanyl derivative with strong selectivity for the μ opioid receptor. At lower doses, it antagonizes the analgesic effects of alfentanil and substitutes for naloxone in morphine-treated monkeys; however, it also reverses naloxone-precipitated withdrawal in pigeons trained to discriminate morphine from naloxone.[1]

At high doses, it exhibits analgesic activity which is not fully reversed by opioid antagonists, suggesting that the drug has both opioid and non-opioid mechanisms of action.[1][2]

Synthesis[edit]

Mirfentanil was synthesized via acylation of the product of the reaction of 2-chloropyrazine and 1-(2-phenylethyl)-4-piperidinone oxime with 2-Furoyl chloride.[3]

See also[edit]

References[edit]

  1. ^ a b France CP, Winger G, Medzihradsky F, Seggel MR, Rice KC, Woods JH. "Mirfentanil: pharmacological profile of a novel fentanyl derivative with opioid and nonopioid effects." Journal of Pharmacology and Experimental Therapeutics. 1991 Aug;258(2):502-10. PMID 1650830
  2. ^ Carr DJ, Brockunier LL, Scott M, Bagley JR, France CP. "Mirfentanil antagonizes morphine-induced suppression of splenic NK activity in mice." Immunopharmacology. 1996 Aug;34(1):9-16. PMID 8880221
  3. ^ Jerome R. Bagley; Wynn, Richard; Rudo, Frieda; Doorley, Brian; Spencer, Kenneth; Spaulding, Theodore (1989). "New 4-(heteroanilido)piperidines, structurally related to the pure opioidagonist fentanyl, with agonist and/or antagonist properties". Journal of Medicinal Chemistry 32 (3): 663–71. doi:10.1021/jm00123a028.