Phenoperidine

Phenoperidine

Clinical data
Routes of administration	Intravenous
ATC code	N01AH04 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage I (Controlled) US: Schedule I
Pharmacokinetic data
Metabolism	Liver
Excretion	Bile and Urine
Identifiers
IUPAC name ethyl 1-(3-hydroxy-3-phenylpropyl)-4-phenylpiperidine-4-carboxylate
CAS Number	562-26-5 N
PubChem CID	11226
ChemSpider	10752 Y
UNII	G9BH09J4JW
KEGG	D02611 Y
ECHA InfoCard	100.008.391
Chemical and physical data
Formula	C23H29NO3
Molar mass	367.481
3D model (Jmol)	Interactive image
SMILES OC(C1=CC=CC=C1)CCN(CC2)CCC2(C3=CC=CC=C3)OC(CC)=O
InChI InChI=1S/C23H29NO3/c1-2-27-22(26)23(20-11-7-4-8-12-20)14-17-24(18-15-23)16-13-21(25)19-9-5-3-6-10-19/h3-12,21,25H,2,13-18H2,1H3 Y Key:IPOPQVVNCFQFRK-UHFFFAOYSA-N Y
NY (what is this?)

Phenoperidine (Operidine or Lealgin), is an opioid used as a general anesthetic.

Phenoperidine is an opioid pain killer -- narcotic analgesic.

It is a derivative of isonipecotic acid, like pethidine, and is metabolized in part to norpethidine. It's potency range is due to method of ingestion. figure 20-80 times as potent as pethidine as an analgesic. The greatly increased potency essentially eliminates the toxic effects of norpethidine accumulation which are seen when pethidine is administered in high doses or for long periods of time.

Phenoperidine was first synthesized in 1957 by Paul Janssen, of the company now known as Janssen Pharmaceutica, who was seeking better opioid pain-killers. His two prototype drugs were methadone and pethidine, each which had been invented in 1930s by Otto Eisleb, who worked for IG Farben. His initial work starting with methadone yielded dextromoramide in 1954. Janssen then turned to making pethidine analogues, due in part to the less complicated chemistry of the compound. During his explorations, he replaced the methyl group attached to the pethidine nitrogen with a propiophenone group, and this yielded phenoperidine, in 1957. Phenoperidine was determined to have decreased stability and enhanced lipophilicity compared to pethidine. Soon after, studies in mice showed that phenoperidine was over 100 times more potent than pethidine.

In 1958, the same line of work yielded “one of the greatest advances of the 20th century psychiatry", haloperidol, as well as diphenoxylate, which lacked the opioid's analgesic properties but still stopped peristalsis in the intestines, a typical side effect of opioids; Janssen brought diphenoxylate to market as a drug to treat diarrhea. And through further advances, Janssen created fentanyl in 1960, which proved to be ten times more potent than phenoperidine.