Phenoperidine was discovered by Janssen Pharmaceutica 1960.^[1] Marketed as its hydrochloride as Operidine or Lealgin, is an opioid used as a general anesthetic. It is a derivative of isonipecotic acid, like pethidine, and is metabolized in part to norpethidine. It is 20-200 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.

In humans 1 milligram is equipotent with 10 mg morphine. It has less effect on the circulatory system and is less hypnotic than morphine, but it has about the same emetic effect. The nausea can be prevented by giving droperidol or haloperidol. After an intravenous dose the analgesia sets in after 3–5 minutes.^[2]

Phenoperidine shares structural similarities with both pethidine and haloperidol (and related butyrophenone antipsychotics, e.g. droperidol). While not commonly used today in clinical practice, it is of historical interest as a precursor in the development of some of the most widely used neuroleptic drugs on the market today.

Opioid Market

Phenoperidine
Clinical data
Routes of; administration	Intravenous
ATC code	N01AH04 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled drug); 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 ;
PubChem CID	11226;
ChemSpider	10752 ;
UNII	G9BH09J4JW;
KEGG	D02611 ;
CompTox Dashboard (EPA)	DTXSID90862199 ;
ECHA InfoCard	100.008.391
Chemical and physical data
Formula	C23H29NO3
Molar mass	367.481 g·mol−1
3D model (JSmol)	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 ; Key:IPOPQVVNCFQFRK-UHFFFAOYSA-N ;
	(what is this?) (verify)

In 2011, the total global morphine equivalent opioid consumption per person was 61.66 mg/capita. While in the Americas, the total morphine equivalent opioid consumption was roughly 750 mg/capita. ^[3]

References

^ BE Patent 576331
^ Farmacevtiska specialiteter i Sverige (FASS) (in Swedish). Stockholm: Linfo. 1983. ISBN 91-85314-44-7.
^ "Regional". Pain & Policy Studies Group. Pain & Policy Studies, University of Wisconsin—Madison. Retrieved 2014-11-24.

External links

Kintz, P.; Godelar, B.; Mangin, P.; Lugnier, A.; Chaumont, A. (1989). "Simultaneous Determination of Pethidine (Meperidine), Phenoperidine, and Norpethidine (Normeperidine), their Common Metabolite, by Gas Chromatography with Selective Nitrogen Detection". Forensic Science International. 43 (3): 267–273. doi:10.1016/0379-0738(89)90154-0. PMID 2613140.{{cite journal}}: CS1 maint: multiple names: authors list (link)
Claris, O.; Bertrix, L. (1988). "Phenoperidine: Pharmacology and Use in Pediatric Resuscitation". Pédiatrie (in French). 43 (6): 509–513. PMID 3186421.{{cite journal}}: CS1 maint: multiple names: authors list (link)
"Antipsychotics - Reference pathway". Kyoto Encyclopedia of Genes and Genomes. Kanehisa Laboratories, Kyoto University, University of Tokyo. Retrieved 2007-01-16.

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

[1] BE Patent 576331

[fass-2] Farmacevtiska specialiteter i Sverige (FASS) (in Swedish). Stockholm: Linfo. 1983. ISBN 91-85314-44-7.

[”pain-3] "Regional". Pain & Policy Studies Group. Pain & Policy Studies, University of Wisconsin—Madison. Retrieved 2014-11-24.

[1]

[2]

[3]