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Compound

Pethidinic acid

Also called Meperidinic acid, Meperidine acid, IDS-NP-004

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Part of the metabolic pathway of Pethidine. See the timeline on the metabolic highway.

Overview

Pethidinic acid (meperidinic acid, pethidine intermediate C) is a 4-phenylpiperidine derivative that is both a metabolite of and a precursor to 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 9234. The 2014 annual manufacturing quota was 6 grams.[1][2][3] WP

Pethidinic acid is a controlled drug because of its potential uses in manufacturing both pethidine itself and some of its substituted derivatives, but it has little opioid activity in its own right. Metabolism of pethidine to pethidinic acid is carried out mainly by the carboxylesterase enzyme hCE-1 in the liver, and since the activity of this enzyme can vary between individuals, the rate and extent of pethidinic acid production can vary.[4][5][6] WP

Frank Wätjen used pethidinic acid as a precursor chemical to a heterocyclic moiety.[7] WP

Chemistry

Formula
C13H17NO2 PC
CAS number
3627-48-3 PC
Molar mass (g/mol)
219.28 PC
IUPAC name (computed by PubChem)
1-methyl-4-phenylpiperidine-4-carboxylic acid PC
SMILES
CN1CCC(CC1)(C2=CC=CC=C2)C(=O)O PC
InChIKey
KHUPPYUUMRDAAX-UHFFFAOYSA-N PC
PubChem CID
101106

Harm reduction information

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Sources

  1. Journal / agency Tompsett SL. The detection and determination of pethidinic acid in urine. Acta Pharmacologica et Toxicologica. 1962. PMID 13985467
  2. Journal / agency Chan K, Lau OW, Wong YC. Determination of pethidine and its major metabolites in human urine by gas chromatography. Journal of Chromatography. April 1991. doi:10.1016/0378-4347(91)80387-R · PMID 1874871
  3. Other Conversion Factors for Controlled Substances
  4. Journal / agency Zhang J, Burnell JC, Dumaual N, Bosron WF. Binding and hydrolysis of meperidine by human liver carboxylesterase hCE-1. The Journal of Pharmacology and Experimental Therapeutics. July 1999. doi:10.1016/S0022-3565(24)34901-8 · PMID 10381793
  5. Journal / agency Wainer IW, Stambaugh JE. GLC determination of meperidinic and normeperidinic acids in urine. Journal of Pharmaceutical Sciences. January 1978. doi:10.1002/jps.2600670131 · PMID 619098
  6. Journal / agency Odar-Cederlöf I, Boréus LO, Bondesson U, Holmberg L, Heyner L. Comparison of renal excretion of pethidine (meperidine) and its metabolites in old and young patients. European Journal of Clinical Pharmacology. 1985. doi:10.1007/BF00609687 · PMID 3987796
  7. Other 4-Phenylpiperidine compounds and their preparation and use

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