Pethidinic acid (meperidinic acid, pethidine intermediate C) is a 4-
phenylpiperidine derivative that is both a
metabolite of and a
precursor to
pethidine (meperidine).[2][3] It is scheduled by
UNSingle 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. [4]
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,[5] and since the activity of this enzyme can vary between individuals, the rate and extent of pethidinic acid production can vary.[6][7]
Frank Wätjen used pethidinic acid as a precursor chemical to a heterocyclic moiety.[8]
^Tompsett SL (1962). "The detection and determination of pethidinic acid in urine". Acta Pharmacologica et Toxicologica. 19: 368–70.
PMID13985467.
^Chan K, Lau OW, Wong YC (April 1991). "Determination of pethidine and its major metabolites in human urine by gas chromatography". Journal of Chromatography. 565 (1–2): 247–54.
doi:
10.1016/0378-4347(91)80387-R.
PMID1874871.
^Zhang J, Burnell JC, Dumaual N, Bosron WF (July 1999). "Binding and hydrolysis of meperidine by human liver carboxylesterase hCE-1". The Journal of Pharmacology and Experimental Therapeutics. 290 (1): 314–8.
PMID10381793.
^Wainer IW, Stambaugh JE (January 1978). "GLC determination of meperidinic and normeperidinic acids in urine". Journal of Pharmaceutical Sciences. 67 (1): 116–8.
doi:
10.1002/jps.2600670131.
PMID619098.
^Odar-Cederlöf I, Boréus LO, Bondesson U, Holmberg L, Heyner L (1985). "Comparison of renal excretion of pethidine (meperidine) and its metabolites in old and young patients". European Journal of Clinical Pharmacology. 28 (2): 171–5.
doi:
10.1007/BF00609687.
PMID3987796.
S2CID20800555.
^EP 0285032, Wätjen, Frank, "4-Phenylpiperidine compounds and their preparation and use", published 1988-10-05, assigned to
Ferrosan A.S.