Norpethidine

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title: "Norpethidine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["convulsants", "synthetic-opioids", "opioid-metabolites", "4-phenylpiperidines", "carboxylate-esters", "ethyl-esters", "human-drug-metabolites", "serotonin–norepinephrine–dopamine-reuptake-inhibitors"] description: "Chemical compound" topic_path: "general/convulsants" source: "https://en.wikipedia.org/wiki/Norpethidine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| verifiedrevid = 421099421 | IUPAC_name = Ethyl 4-phenylpiperidine-4-carboxylate | image = Norpethidine2DACS.svg | image_class = skin-invert-image | width = 190 | image2 = Norpethidine_27feb.gif

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = Unscheduled | legal_BR = A1 | legal_BR_comment = | legal_CA = Schedule I | legal_UK = | legal_US = Schedule II | legal_UN = N I | legal_DE = Anlage II

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 77-17-8 | ATC_prefix = none | ATC_suffix = | PubChem = 32414 | KEGG = C22685 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 30039 | ChEMBL_Ref = | ChEMBL = 1052 | UNII_Ref = | UNII = JG096PMW2N

| C = 14 | H = 19 | N = 1 | O = 2 | smiles = O=C(OCC)C2(c1ccccc1)CCNCC2 | StdInChI_Ref = | StdInChI = 1S/C14H19NO2/c1-2-17-13(16)14(8-10-15-11-9-14)12-6-4-3-5-7-12/h3-7,15H,2,8-11H2,1H3 | StdInChIKey_Ref = | StdInChIKey = QKHMFBKXTNQCTM-UHFFFAOYSA-N | synonyms =

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.

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.

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.

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.

Precursor Use

Norpethidine can be used as a precursor in synthesis of other drugs, including etoxeridine, benzethidine, furethidine, morpheridine, anileridine, phenoperidine, piminodine, oxpheneridine, pheneridine & carperidine.

References

References

1. Anvisa. (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
2. "Conversion Factors for Controlled Substances". Drug Enforcement Administration (DEA), U.S. Department of Justice.
3. (October 1982). "Antinociceptive activity and toxicity of meperidine and normeperidine in mice". The Journal of Pharmacology and Experimental Therapeutics.
4. (January 1995). "Behavioural effects of norpethidine, a metabolite of pethidine, in rats". Toxicology.
5. (January 2002). "Use of meperidine in patient-controlled analgesia and the development of a normeperidine toxic reaction". Archives of Surgery.
6. (November 1993). "Norpethidine toxicity and patient controlled analgesia". British Journal of Anaesthesia.
7. 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.
8. (August 1981). "Presystemic metabolism of meperidine to normeperidine in normal and cirrhotic subjects". Clinical Pharmacology and Therapeutics.
9. (December 1989). "Norpethidine induced myoclonus in a patient with renal failure". Journal of Neurology, Neurosurgery, and Psychiatry.
10. (November 1987). "Possible roles of normeperidine and hyponatremia in a postoperative death". Canadian Medical Association Journal.
11. (March 1992). "Lethal effects of normeperidine". The American Journal of Forensic Medicine and Pathology.
12. (September 2004). "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.
13. (June 1999). "Norpethidine accumulation and generalized seizure during pethidine patient-controlled analgesia". Anaesthesia and Intensive Care.
14. "New piperidine derivatives".
15. (1958). "622. Some new analogues of pethidine. Part III. 1-Aryloxy-alkylnorpethidines, and close analogues.". Journal of the Chemical Society (Resumed).
16. (1960). "426. Some new analogues of pethidine. Part IV. Substituents at the 1-position incorporating cyclic ether groups.". Journal of the Chemical Society (Resumed).

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