Picenadol
Picenadol is a 4-phenylpiperidine derivative that is an opioid analgesic drug developed by Eli Lilly in the 1970s.
Picenadol is an effective analgesic with similar efficacy to pethidine. It has been investigated for some applications such as obstetrics and dentistry, but never commercialised.
It is unusual in that one enantiomer is a pure μ-opioid agonist, while the other is an antagonist. The isomer is the agonist, while is antagonist. This means that the racemic mix of the two enantiomers is a mixed agonist-antagonist, with relatively low abuse potential, and little of the κ-opioid activity that tends to cause problems with other opioid mixed agonist-antagonists such as pentazocine.Synthesis