Pethidinic acid

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Pethidinic acid
Pethidinicacid.svg
Systematic (IUPAC) name
1-methyl-4-phenylpiperidine-4-carboxylic acid
Clinical data
Legal status
Routes N/A
Identifiers
CAS number 3627-48-3 YesY
ATC code None
PubChem CID 101106
ChemSpider 91344 N
ChEMBL CHEMBL1201376 N
Chemical data
Formula C13H17NO2 
Mol. mass 219.28 g/mol
 N (what is this?)  (verify)

Pethidinic acid (meperidinic acid, pethidine intermediate C) is a 4-phenylpiperidine derivative that is both a metabolite of and a precursor to pethidine (meperidine).[1][2] It is scheduled by UN Single Convention on Narcotic Drugs.

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,[3] and since the activity of this enzyme can vary between individuals, the rate and extent of pethidinic acid production can vary.[4][5]

See also[edit]

References[edit]

  1. ^ Tompsett SL. The detection and determination of pethidinic acid in urine. Acta Pharmacologica et Toxicologica (Copenhagen). 1962;19:368-70.
  2. ^ Chan K, Lau OW, Wong YC. Determination of pethidine and its major metabolites in human urine by gas chromatography. Journal of Chromatography. 1991 Apr 19;565(1-2):247-54.
  3. ^ Zhang J, Burnell JC, Dumaual N, Bosron WF. Binding and hydrolysis of meperidine by human liver carboxylesterase hCE-1. Journal of Pharmacology and Experimental Therapeutics. 1999 Jul;290(1):314-8.
  4. ^ Wainer IW, Stambaugh JE. GLC determination of meperidinic and normeperidinic acids in urine. Journal of Pharmaceutical Sciences. 1978 Jan;67(1):116-8.
  5. ^ Odar-Cederlof I, Boreus 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;28(2):171-5.