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{{Short description|Chemical compound}} |
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{{drugbox | |
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{{Drugbox |
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| IUPAC_name = 1-methyl-4-phenylpiperidine-4-carboxylic acid |
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| Verifiedfields = changed |
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| image = Pethidinicacid.svg |
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| Watchedfields = changed |
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| width = 160 |
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| verifiedrevid = 412260866 |
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| CAS_number = 3627-48-3 |
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| IUPAC_name = 1-methyl-4-phenylpiperidine-4-carboxylic acid |
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| synonyms = |
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| image = Pethidinicacid.svg |
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| ATC_prefix = none |
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| image_class = skin-invert-image |
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| ATC_suffix = |
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| width = 160 |
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| PubChem = 101106 |
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| DrugBank = |
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<!--Clinical data--> |
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| C = 13 | H = 17 | N = 1 | O = 2 |
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| tradename = |
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| molecular_weight = 219.28 g/mol |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| bioavailability = |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| protein_bound = |
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| pregnancy_category = |
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| metabolism = |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| elimination_half-life = |
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| excretion = |
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| legal_BR = A1 |
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| legal_BR_comment = <ref>{{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=] |language=pt-BR |publication-date=2023-04-04}}</ref> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| legal_CA = <!-- Schedule I --> |
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| legal_UK = <!-- Class A --> |
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| pregnancy_category= |
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| legal_US = <!-- Schedule I --> |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_UN = N I |
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| legal_CA = <!-- Schedule I --> |
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| legal_DE = Anlage II |
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| legal_UK = <!-- Class A --> |
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| legal_US = <!-- Schedule I --> |
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| legal_status = |
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| routes_of_administration = N/A |
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| routes_of_administration = N/A |
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<!--Pharmacokinetic data--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 3627-48-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 4ZGQ154PQY |
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| ATC_prefix = none |
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| ATC_suffix = |
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| PubChem = 101106 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C22798 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1201376 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 91344 |
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<!--Chemical data--> |
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| C=13 | H=17 | N=1 | O=2 |
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| synonyms = |
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| smiles = CN1CCC(CC1)(C2=CC=CC=C2)C(=O)O |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = KHUPPYUUMRDAAX-UHFFFAOYSA-N |
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}} |
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'''Pethidinic acid''' ('''meperidinic acid''', '''pethidine intermediate C''') is a 4-]] derivative that is both a ] of and a ] to ] (meperidine).<ref>Tompsett SL. The detection and determination of pethidinic acid in urine. ''Acta Pharmacologica et Toxicologica (Copenhagen)''. 1962;19:368-70.</ref><ref>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.</ref> |
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'''Pethidinic acid''' ('''meperidinic acid''', '''pethidine intermediate C''') is a 4-]] derivative that is both a ] of and a ] to ] (meperidine).<ref name="pmid13985467">{{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 }}</ref><ref name="pmid1874871">{{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}}</ref> It is scheduled by ] ]. 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. <ref>{{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 }}</ref> |
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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 ] activity in its own right. Metabolism of pethidine to pethidinic acid is carried out mainly by the ] enzyme hCE-1 in the liver,<ref>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.</ref> and since the activity of this enzyme can vary between individuals, the rate and extent of pethidinic acid production can vary.<ref>Wainer IW, Stambaugh JE. GLC determination of meperidinic and normeperidinic acids in urine. ''Journal of Pharmaceutical Sciences''. 1978 Jan;67(1):116-8.</ref><ref>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.</ref> |
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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 ] activity in its own right. Metabolism of pethidine to pethidinic acid is carried out mainly by the ] enzyme hCE-1 in the liver,<ref name="pmid10381793">{{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 | pmid = 10381793 }}</ref> and since the activity of this enzyme can vary between individuals, the rate and extent of pethidinic acid production can vary.<ref name="pmid619098">{{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 }}</ref><ref name="pmid3987796">{{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 }}</ref> |
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Frank Wätjen used pethidinic acid as a precursor chemical to a heterocyclic moiety.<ref>{{Cite patent|country=EP|number=0285032|title=4-Phenylpiperidine compounds and their preparation and use|pubdate=1988-10-05| |
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assign=]|inventor1-last=Wätjen |inventor1-first=Frank}}</ref> |
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==See also== |
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==See also== |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] (norpethidine) |
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== References == |
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== References == |
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{{Reflist|2}} |
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{{opioids}} |
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