Structure via PubChem · Public domain (PubChem)
normeperidine
Sign in to saveAlso known as norpethidine
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 .
Chemical data
- Formula
- C14H19NO2
- Molecular weight
- 233.31 g/mol
- IUPAC name
- ethyl 4-phenylpiperidine-4-carboxylate
- SMILES
- CCOC(=O)C1(CCNCC1)C2=CC=CC=C2
- InChIKey
- QKHMFBKXTNQCTM-UHFFFAOYSA-N
- XLogP
- 2
- Polar surface area
- 38.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
163 papers- Normeperidine toxicity.Anesthesia and analgesia · 1986
- Recognizing normeperidine toxicity.Nursing · 2003
- Disposition of meperidine and normeperidine following multiple doses during labor. I. Mother.American journal of obstetrics and gynecology · 1985
- Pharmacology.International anesthesiology clinics · 1999
- Clearance of meperidine and its metabolite normeperidine in hemodialysis patients with chronic noncancer pain.Journal of pain and symptom management · 2014
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 233.142
Show 4 more facts
- chemical formula
- C₁₄H₁₉NO₂
- canonical SMILES
- CCOC(=O)C1(CCNCC1)C2=CC=CC=C2
- subject has role
- acetylcholinesterase inhibitor
- Commons category
- Norpethidine
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Precursor Use
- See also
- References
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 .
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.
Excerpted from Wikipedia’s “normeperidine” article, available under the CC BY-SA 4.0 licence.