Chemistry:Pethidinic acid
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| Routes of administration | N/A |
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| Formula | C13H17NO2 |
| Molar mass | 219.284 g·mol−1 |
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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] It is scheduled by United Nations 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. [3]
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,[4] and since the activity of this enzyme can vary between individuals, the rate and extent of pethidinic acid production can vary.[5][6]
Frank Wätjen used pethidinic acid as a precursor chemical to a heterocyclic moiety.[7]
See also
- Moramide intermediate
- Methadone intermediate
- Pethidine intermediate A
- Pethidine intermediate B (norpethidine)
References
- ↑ "The detection and determination of pethidinic acid in urine". Acta Pharmacologica et Toxicologica 19: 368–70. 1962. PMID 13985467.
- ↑ "Determination of pethidine and its major metabolites in human urine by gas chromatography". Journal of Chromatography 565 (1–2): 247–54. April 1991. doi:10.1016/0378-4347(91)80387-R. PMID 1874871.
- ↑ "Conversion Factors for Controlled Substances". DEA Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice. http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html.
- ↑ "Binding and hydrolysis of meperidine by human liver carboxylesterase hCE-1". The Journal of Pharmacology and Experimental Therapeutics 290 (1): 314–8. July 1999. PMID 10381793.
- ↑ "GLC determination of meperidinic and normeperidinic acids in urine". Journal of Pharmaceutical Sciences 67 (1): 116–8. January 1978. doi:10.1002/jps.2600670131. PMID 619098.
- ↑ "Comparison of renal excretion of pethidine (meperidine) and its metabolites in old and young patients". European Journal of Clinical Pharmacology 28 (2): 171–5. 1985. doi:10.1007/BF00609687. PMID 3987796.
- ↑ Wätjen, Frank, "4-Phenylpiperidine compounds and their preparation and use", EP patent 0285032, published 1988-10-05
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