Norpethidine

Overview

Norpethidine (normeperidine, pethidine intermediate B) is a 4-phenylpiperidine derivative that is both a precursor to, and the toxic metabolite of, pethidine (meperidine). It is scheduled by UN Single Convention on Narcotic Drugs. It is a Schedule II Narcotic controlled substance in the United States and has an ACSCN of 9233. The 2014 annual manufacturing quota was 11 g.[1] WP⚠ The source also gives this in other units.

Norpethidine is a controlled drug because of its potential uses in manufacturing both pethidine itself and a range of N-substituted derivatives, but it has little opioid activity in its own right. Instead, norpethidine acts as a stimulant and causes convulsions.[2][3] WP

Bioaccumulation of norpethidine is a major complication when pethidine is used in medicine as an analgesic, as when pethidine is used in high doses or administered by intravenous infusion, norpethidine can accumulate in the body at a faster rate than it is being excreted, particularly in elderly patients or those with compromised liver or kidney function, resulting in a range of toxic effects, mainly convulsions, but also myoclonus and hyponatremia. These complications can be serious and have sometimes resulted in death.[4–10] WP

Metabolism of pethidine to norpethidine is carried out mainly by the CYP enzymes, CYP2B6, CYP2C19 and CYP3A4, in the liver, and since the activity of these enzymes can vary between individuals and can be influenced by concurrent use of other drugs, the rate and extent of norpethidine production can be difficult to predict.[11][12] WP

Chemistry

Formula

C14H19NO2 PC

CAS number

77-17-8 PC

Molar mass (g/mol)

233.31 PC

IUPAC name (computed by PubChem)

ethyl 4-phenylpiperidine-4-carboxylate PC

SMILES

CCOC(=O)C1(CCNCC1)C2=CC=CC=C2 PC

InChIKey

QKHMFBKXTNQCTM-UHFFFAOYSA-N PC

PubChem CID

32414

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Conversion Factors for Controlled Substances
2. Journal / agency Umans JG, Inturrisi CE. Antinociceptive activity and toxicity of meperidine and normeperidine in mice. The Journal of Pharmacology and Experimental Therapeutics. October 1982. doi:10.1016/S0022-3565(25)33313-6 · PMID 7120119
3. Journal / agency Plummer JL, Gourlay GK, Cmielewski PL, Odontiadis J, Harvey I. Behavioural effects of norpethidine, a metabolite of pethidine, in rats. Toxicology. January 1995. doi:10.1016/0300-483x(94)02871-q · PMID 7825188
4. Journal / agency Simopoulos TT, Smith HS, Peeters-Asdourian C, Stevens DS. Use of meperidine in patient-controlled analgesia and the development of a normeperidine toxic reaction. Archives of Surgery. January 2002. doi:10.1001/archsurg.137.1.84 · PMID 11772223
5. Journal / agency Stone PA, Macintyre PE, Jarvis DA. Norpethidine toxicity and patient controlled analgesia. British Journal of Anaesthesia. November 1993. doi:10.1093/bja/71.5.738 · PMID 8251291
6. Other Holmberg L, Odar-Cederlof I, Boreus LO, Heyner L, Ehrnebo M. Comparative disposition of pethidine and norpethidine in old and young patients. European Journal of Clinical Pharmacology. 1982;22(2):175-9
7. Journal / agency Pond SM, Tong T, Benowitz NL, Jacob P, Rigod J. Presystemic metabolism of meperidine to normeperidine in normal and cirrhotic subjects. Clinical Pharmacology and Therapeutics. August 1981. doi:10.1038/clpt.1981.146 · PMID 7249503
8. Journal / agency Reutens DC, Stewart-Wynne EG. Norpethidine induced myoclonus in a patient with renal failure. Journal of Neurology, Neurosurgery, and Psychiatry. December 1989. doi:10.1136/jnnp.52.12.1450 · PMID 2614458 · PMC1031622
9. Journal / agency Appel WC. Possible roles of normeperidine and hyponatremia in a postoperative death. Canadian Medical Association Journal. November 1987. PMID 3676934 · PMC1267380
10. Journal / agency Jiraki K. Lethal effects of normeperidine. The American Journal of Forensic Medicine and Pathology. March 1992. doi:10.1097/00000433-199203000-00009 · PMID 1585886
11. Journal / agency Ramírez J, Innocenti F, Schuetz EG, Flockhart DA, Relling MV, Santucci R, Ratain MJ. CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes. Drug Metabolism and Disposition: The Biological Fate of Chemicals. September 2004. doi:10.1016/S0090-9556(24)02975-1 · PMID 15319333
12. Journal / agency McHugh GJ. Norpethidine accumulation and generalized seizure during pethidine patient-controlled analgesia. Anaesthesia and Intensive Care. June 1999. PMID 10389564

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