Pethidinic acid

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

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| verifiedrevid = 412260866

| IUPAC_name = 1-methyl-4-phenylpiperidine-4-carboxylic acid

| image = Pethidinicacid.svg

| image_class = skin-invert-image

| width = 160

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| pregnancy_AU =

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| legal_AU =

| legal_BR = A1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA =

| legal_UK =

| legal_US =

| legal_UN = N I

| legal_DE = Anlage II

| routes_of_administration = N/A

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 3627-48-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4ZGQ154PQY

| ATC_prefix = none

| ATC_suffix =

| PubChem = 101106

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C22798

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1201376

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 91344

| C=13 | H=17 | N=1 | O=2

| synonyms =

| smiles = CN1CCC(CC1)(C2=CC=CC=C2)C(=O)O

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = KHUPPYUUMRDAAX-UHFFFAOYSA-N

}}

Pethidinic acid (meperidinic acid, pethidine intermediate C) is a 4-phenylpiperidine derivative that is both a metabolite of and a precursor to pethidine (meperidine).{{cite journal | vauthors = Tompsett SL | title = The detection and determination of pethidinic acid in urine | journal = Acta Pharmacologica et Toxicologica | volume = 19 | pages = 368–70 | date = 1962 | pmid = 13985467 }}{{cite journal | vauthors = Chan K, Lau OW, Wong YC | title = Determination of pethidine and its major metabolites in human urine by gas chromatography | journal = Journal of Chromatography | volume = 565 | issue = 1–2 | pages = 247–54 | date = April 1991 | pmid = 1874871 | doi = 10.1016/0378-4347(91)80387-R}} 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. {{Cite web | title = Conversion Factors for Controlled Substances | url=http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html | work = DEA Diversion Control Division | publisher = Drug Enforcement Agency, U.S. Department of Justice }}

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,{{cite journal | vauthors = Zhang J, Burnell JC, Dumaual N, Bosron WF | title = Binding and hydrolysis of meperidine by human liver carboxylesterase hCE-1 | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 290 | issue = 1 | pages = 314–8 | date = July 1999 | doi = 10.1016/S0022-3565(24)34901-8 | pmid = 10381793 }} and since the activity of this enzyme can vary between individuals, the rate and extent of pethidinic acid production can vary.{{cite journal | vauthors = Wainer IW, Stambaugh JE | title = GLC determination of meperidinic and normeperidinic acids in urine | journal = Journal of Pharmaceutical Sciences | volume = 67 | issue = 1 | pages = 116–8 | date = January 1978 | pmid = 619098 | doi = 10.1002/jps.2600670131 }}{{cite journal | vauthors = Odar-Cederlöf I, Boréus LO, Bondesson U, Holmberg L, Heyner L | title = Comparison of renal excretion of pethidine (meperidine) and its metabolites in old and young patients | journal = European Journal of Clinical Pharmacology | volume = 28 | issue = 2 | pages = 171–5 | date = 1985 | pmid = 3987796 | doi = 10.1007/BF00609687 | s2cid = 20800555 }}

Frank Wätjen used pethidinic acid as a precursor chemical to a heterocyclic moiety.{{Cite patent|country=EP|number=0285032|title=4-Phenylpiperidine compounds and their preparation and use|pubdate=1988-10-05|

assign=Ferrosan A.S.|inventor1-last=Wätjen |inventor1-first=Frank}}