Picenadol (LY-97435) is a 4-

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen ...

piperidine Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor de ...

derivative that is an

opioid Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioid use ...

analgesic drug developed by Eli Lilly in the 1970s. Picenadol is an effective analgesic with similar efficacy to

pethidine Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Otto Eis ...

(meperidine). 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 (3R,4R) isomer is the agonist, while (3S,4S) is antagonist.Froimowitz M, Cody V. Absolute configurations and conformations of the opioid agonist and antagonist enantiomers of picenadol. ''Chirality''. 1995;7(7):518-25. This means that the racemic mix of the two enantiomers is a mixed agonist-antagonist, with relatively low

abuse potential Substance abuse, also known as drug abuse, is the use of a drug in amounts or by methods which are harmful to the individual or others. It is a form of substance-related disorder. Differing definitions of drug abuse are used in public health, ...

, and little of the κ-opioid activity that tends to cause problems with other opioid mixed agonist-antagonists such as

pentazocine Pentazocine, sold under the brand name Talwin among others, is a painkiller used to treat moderate to severe pain. It is believed to work by activating (agonizing) κ-opioid receptors (KOR) and μ-opioid receptors (MOR). As such it is called an ...

Synthesis

References

Synthetic opioids 4-Phenylpiperidines Phenols Mu-opioid receptor agonists {{analgesic-stub

Synthesis

See also

References