Pethidinic acid

Pethidinic acid
Clinical data
Routes of; administration	N/A
ATC code	none;
Legal status
Legal status	DE: Anlage II (Authorized trade only, not prescriptible); UN: Narcotic Schedule I;
Identifiers
	IUPAC name 1-methyl-4-phenylpiperidine-4-carboxylic acid;
CAS Number	3627-48-3 ;
PubChem CID	101106;
ChemSpider	91344 ;
ChEMBL	ChEMBL1201376 ;
CompTox Dashboard (EPA)	DTXSID30189812 ;
Chemical and physical data
Formula	C13H17NO2
Molar mass	219.28 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCC(CC1)(C2=CC=CC=C2)C(=O)O;
	InChI InChI=1S/C13H17NO2/c1-14-9-7-13(8-10-14,12(15)16)11-5-3-2-4-6-11/h2-6H,7-10H2,1H3,(H,15,16) ; Key:KHUPPYUUMRDAAX-UHFFFAOYSA-N ;
	(what is this?) (verify)

Pethidinic acid (meperidinic acid, pethidine intermediate C) is a 4-phenyl piperidine 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]

References

^ Tompsett SL. The detection and determination of pethidinic acid in urine. Acta Pharmacologica et Toxicologica (Copenhagen). 1962;19:368-70.
^ 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.
^ 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.
^ Wainer IW, Stambaugh JE. GLC determination of meperidinic and normeperidinic acids in urine. Journal of Pharmaceutical Sciences. 1978 Jan;67(1):116-8.
^ 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.

This pharmacology-related article is a stub. You can help Wikipedia by expanding it.

[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.

[1]

[2]

[3]

[4]

[5]

See also

References