Pethidinic acid (meperidinic acid, pethidine intermediate C) is a 4-
phenyl
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydroge ...
piperidine
Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic compound, heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless ...
derivative that is both a
metabolite
In biochemistry, a metabolite is an intermediate or end product of metabolism.
The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, ...
of and a
precursor
Precursor or Precursors may refer to:
*Precursor (religion), a forerunner, predecessor
** The Precursor, John the Baptist
Science and technology
* Precursor (bird), a hypothesized genus of fossil birds that was composed of fossilized parts of un ...
to
pethidine
Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Otto Ei ...
(meperidine).
It is scheduled by
UN Single Convention on Narcotic Drugs
The Single Convention on Narcotic Drugs, 1961 (Single Convention, 1961 Convention, or C61) is an Treaty, international treaty that controls activities (cultivation, production, supply, trade, transport) of specific narcotic drugs and lays down ...
. 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.
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
Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioi ...
activity in its own right. Metabolism of pethidine to pethidinic acid is carried out mainly by the
carboxylesterase
The enzyme carboxylesterase (or carboxylic-ester hydrolase, EC 3.1.1.1; systematic name carboxylic-ester hydrolase) catalyzes reactions of the following form:
:a carboxylic ester + H2O \rightleftharpoons an alcohol + a carboxylate
Most enzymes fr ...
enzyme hCE-1 in the liver,
and since the activity of this enzyme can vary between individuals, the rate and extent of pethidinic acid production can vary.
Frank Wätjen used pethidinic acid as a precursor chemical to a heterocyclic moiety.
See also
*
Moramide intermediate
Moramide intermediate (3-methyl-4-morpholin-4-yl-2,2-diphenylbutanoic acid, on INCB Yellow List as 2-methyl-3-morpholino-1,1-diphenylpropane carboxylic acid) is a moramide precursor scheduled by UN Single Convention on Narcotic Drugs.
In the Un ...
*
Methadone intermediate
Methadone intermediate is a methadone precursor 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 9254. The 2014 annual manufacturing quota was ...
*
Pethidine intermediate A
Pethidine intermediate A is a 4- phenyl piperidine derivative that is a precursor to the opioid analgesic drug pethidine (meperidine). It is not known to have any analgesic activity in its own right, however other derivatives of pethidine with a ...
*
Pethidine intermediate B (norpethidine)
References
Synthetic opioids
4-Phenylpiperidines
Carboxylic acids
Human drug metabolites
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