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Pethidinic Acid


Pethidinic Acid
Systematic (IUPAC) name
1-methyl-4-phenylpiperidine-4-carboxylic acid
Identifiers
CAS number	3627-48-3
ATC code	?
PubChem	101106
Chemical data
Formula	C₁₃H₁₇N O₂
Mol. mass	219.28 g/mol
Synonyms	Pethidinic acid, Meperidinic acid, Pethidine Intermediate C
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	N/A

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]

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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.

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Opioids

Opiate derivatives

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Morphinans

Butorphanol • Cyclorphan • Dextro-3-hydroxy-N-allylmorphinan • Dextrorphan • Drotebanol • Levargorphan • Levallorphan • Levorphanol • Levorphan • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Racemethorphan • Racemorphan

Benzomorphans

Bremazocine • Cyclazocine • Dezocine • Ethylketocyclazocine • Ketazocine • Metazocine • Pentazocine • Phenazocine

4-Phenylpiperidines

Pethidines (Meperidines)	Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Morpheridine • Oxpheneridine (Carbamethidine) • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine • WIN-7681
Prodines	Allylprodine • α-meprodine • α-prodine • β-meprodine • β-prodine • Meprodine • MPPP • PEPAP • Prodine • Prosidol • Trimeperidine
Ketobemidones	Acetoxyketobemidone • Ketobemidone • Methylketobemidone • Propylketobemidone
Others	Alvimopan • Loperamide • Picenadol

Open Chain Opioids

Amidones	Dextromethadone • Dipipanone • Isomethadone • Levomethadone • Methadone • Methadone Intermediate • Norpipanone • Phenadoxone (Heptazone) • Pipidone
Methadols	Acetylmethadol • α-methadol • α-acetylmethadol • β-methadol • β-acetylmethadol • Dimepheptanol • Levo-α-acetylmethadol • Noracymethadol
Moramides	Dextromoramide • Levomoramide • Moramide Intermediate • Racemoramide
Thiambutenes	Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene
Phenalkoxams	Dextropropoxyphene • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Propoxyphene
Ampromides	Diampromide • Phenampromide • Propiram
Others	Lefetamine