Norpethidine

Norpethidine
Clinical data


Routes of administration	N/A
ATC code	none
Legal status
Legal status	AU: Unscheduled CA: Schedule I DE: Anlage II (Prohibited) US: Schedule II UN: Narcotic Schedule I
Identifiers
IUPAC name Ethyl 4-phenylpiperidine-4-carboxylate
CAS Number	77-17-8^Y
PubChem (CID)	32414
ChemSpider	30039^Y
UNII	JG096PMW2N^Y
ChEMBL	CHEMBL1052^Y
ECHA InfoCard	100.000.918
Chemical and physical data
Formula	C₁₄H₁₉NO₂
Molar mass	233.31 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(OCC)C2(c1ccccc1)CCNCC2
InChI InChI=1S/C14H19NO2/c1-2-17-13(16)14(8-10-15-11-9-14)12-6-4-3-5-7-12/h3-7,15H,2,8-11H2,1H3^Y Key:QKHMFBKXTNQCTM-UHFFFAOYSA-N^Y

Norpethidine (normeperidine, pethidine intermediate B) is a 4-phenylpiperidine derivative that is both a metabolite of and a precursor to pethidine (meperidine). 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 9233. The 2014 annual manufacturing quota was 11 grammes.

Norpethidine is a controlled drug because of its potential uses in manufacturing both pethidine itself and a range of N-substituted derivatives, but it has little opioid activity in its own right. Instead, norpethidine acts as a stimulant and causes convulsions.

Build up of norpethidine is a major complication when pethidine is used in medicine as an analgesic, as when pethidine is used in high doses or administered by intravenous infusion, norpethidine can accumulate in the body at a faster rate than it is being excreted, particularly in elderly patients or those with compromised liver or kidney function, resulting in a range of toxic effects, mainly convulsions, but also myoclonus and hyponatremia. These complications can be serious and have sometimes resulted in death.

Metabolism of pethidine to norpethidine is carried out mainly by the enzymes, CYP2B6, CYP2C19 and CYP3A4, in the liver, and since the activity of these enzymes can vary between individuals and can be influenced by concurrent use of other drugs, the rate and extent of norpethidine production can be difficult to predict.

Norpethidine can be used as a precuror in synthesis of other drugs, including etoxeridine,benzethidine,furethidine,morpheridine, anileridine, phenoperidine, Piminodine and oxpheneridine.

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