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]
Side effects of
fentanyl analogs are similar to those of fentanyl itself, which include
itching,
nausea and potentially serious
respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.[3]
Synthesis
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.[4]
^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.
PMID2563773.