Norpethidine

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Norpethidine
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Clinical data
Routes of
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N/A
ATC code
  • none
Legal status
Legal status
Identifiers
  • Ethyl 4-phenylpiperidine-4-carboxylate
CAS Number
PubChem CID
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UNII
KEGG
ChEMBL
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Chemical and physical data
Formula C14H19NO2
Molar mass 233.311 g·mol−1
3D model (JSmol)
  • O=C(OCC)C2(c1ccccc1)CCNCC2
  • 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 Yes check.svgY
  • Key:QKHMFBKXTNQCTM-UHFFFAOYSA-N Yes check.svgY
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Norpethidine (normeperidine, pethidine intermediate B) is a 4-phenylpiperidine derivative that is both a precursor to, and the toxic metabolite of, 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 grams (0.39 oz). [2]

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. [3] [4]

Bioaccumulation of norpethidine is a major complication when pethidine is used in medicine as an analgesic, as when pethidine is used in high doses [5] or administered by intravenous infusion, [6] norpethidine can accumulate in the body at a faster rate than it is being excreted, particularly in elderly patients [7] or those with compromised liver or kidney function, [8] resulting in a range of toxic effects, mainly convulsions, but also myoclonus [9] and hyponatremia. [10] These complications can be serious and have sometimes resulted in death. [11]

Metabolism of pethidine to norpethidine is carried out mainly by the CYP 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. [12] [13]

Norpethidine can be used as a precursor in synthesis of other drugs, including etoxeridine, [14] benzethidine, [15] furethidine, [16] morpheridine, anileridine, phenoperidine, piminodine and oxpheneridine.

See also

Related Research Articles

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Benzethidine is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine.

<span class="mw-page-title-main">Furethidine</span> Chemical compound

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Morpheridine (Morpholinoethylnorpethidine) is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine). It is a strong analgesic with around 4 times the potency of pethidine, and unlike pethidine, does not cause convulsions, although it produces the standard opioid side effects such as sedation and respiratory depression.

<span class="mw-page-title-main">Oxpheneridine</span> Chemical compound

Oxpheneridine is a 4-phenylpiperidine derivative that is related to the opioid analgesic drug pethidine (meperidine).

<span class="mw-page-title-main">Pethidine intermediate A</span> Chemical compound

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References

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