3627-48-3

Basic information

• Product Name: PETHIDINIC ACID
• Synonyms: PETHIDINIC ACID;1-Methyl-4-phenyl-4-piperidinecarboxylic acid;Meperidine acid;1-methyl-4-phenyl-isonipecotic acid;1-methyl-4-phenyl-piperidine-4-carboxylic acid;1-methyl-4-phenylpiperidine-4-carboxylic acid;1-methyl-4-phenylpiperidine-4-carboxylic acid(SALTDATA: H2O);KHUPPYUUMRDAAX-UHFFFAOYSA-N
• CAS NO: 3627-48-3
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 0
• Mol File: 3627-48-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 360.9°Cat760mmHg
• Flash Point: 172.1°C
• Appearance: /
• Density: 1.139g/cm³
• Vapor Pressure: 7.71E-06mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: PETHIDINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: PETHIDINIC ACID(3627-48-3)
• EPA Substance Registry System: PETHIDINIC ACID(3627-48-3)

Safety Data

• Hazardous Substances Data: 3627-48-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H17NO2/c1-14-9-7-13(8-10-14,12(15)16)11-5-3-2-4-6-11/h2-6H,7-10H2,1H3,(H,15,16)

Upstream product

• 50-13-5 meperidine hydrochloride 
• 71258-18-9 1-benzyl-4-phenyl-piperidine-4-carbonitrile; hydrochloride 
• 51-75-2 nitrogen mustard 
• 140-29-4 phenylacetonitrile 
• 92039-99-1 (1-methyl-[4]piperidyl)-phenyl ketone; hydrochloride 
• 100119-73-1 1,5-dichloro-3-cyano-3-phenylpentane 
• 56-23-5 tetrachloromethane 
• 107054-93-3 (4-chloro-1-methyl-[4]piperidyl)-phenyl ketone 
• 57-42-1 pethidine 
• 3627-62-1 1-methyl-4-phenyl-piperidine-4-carbonitrile 

Downstream Products

• 57-42-1 pethidine 
• 96004-85-2 bis-(1-methyl-4-phenyl-[4]piperidylmethyl)-amine 
• 60257-12-7 1-methyl-4-phenyl-piperidine-4-carbonyl chloride ; hydrochloride 
• 3691-79-0 1-methyl-4-phenyl-piperidine-4-carbaldehyde 
• 774-52-7 1-methyl-4-phenylpiperidine 

Relevant articles and documents

Impact of cytochrome P450 variation on meperidine N-demethylation to the neurotoxic metabolite normeperidine

1. Meperidine is an opioid analgesic that undergoes N-demethylation to form the neurotoxic metabolite normeperidine. Previous studies indicate that meperidine N-demethylation is catalyzed by cytochrome P450 2B6 (CYP2B6), CYP3A4, and CYP2C19. 2. The purpose of this study was to examine the relative P450 contributions to meperidine N-demethylation and to evaluate the effect of CYP2C19 polymorphism on normeperidine generation. Experiments were performed using recombinant P450 enzymes, selective chemical inhibitors, enzyme kinetic assays, and correlation analysis with individual CYP2C19-genotyped human liver microsomes. 3. The catalytic efficiency (kcat/Km) for meperidine N-demethylation was similar between recombinant CYP2B6 and CYP2C19, but markedly lower by CYP3A4. 4. In CYP2C19-genotyped human liver microsomes, normeperidine formation was significantly correlated with CYP2C19 activity (S-mephenytoin 4′-hydroxylation). 5. CYP2C19 inhibitor (+)-N-3-benzylnirvanol and CYP3A inhibitor ketoconazole significantly reduced microsomal normeperidine generation by an individual donor with high CYP2C19 activity, whereas donors with lower CYP2C19 activity were sensitive to inhibition by ketoconazole but not benzylnirvanol. 6. These findings demonstrate that the relative CYP3A4, CYP2B6, and CYP2C19 involvement in meperidine N-demethylation depends on the enzyme activities in individual human liver microsomal samples. CYP2C19 is likely an important contributor to normeperidine generation in individuals with high CYP2C19 activity, but additional factors influence inter-individual metabolite accumulation.

TLC identification adn GLC determination of meperidine and its metabolites in biological fluids.

Procedures were developed for TLC identification and GLC determination of meperidine and its metabolites, i.e., p-hydroxymeperidine, normeperidine, and meperidinic and normeperidinic acids. Meperidine, p-hydroxymeperidine, and normeperidine were extracted with ether from biological fluids at pH 10, whereas meperidinic and normeperidinic acids and conjugated metabolites remained in the aqueous phase. The residue, upon evaporation of the extract to dryness, was derivatized with trifluoroacetic anhydride and gas chromatographed. Total (free and conjugated) meperidinic and normeperidinic acids in the aqueous phase were converted and determined as meperidine and normeperidine, respectively. A preliminary result of urinary disposition of meperidine and its metabolites in the rat is presented. The identity of these metabolites was confirmed with GLC-mass spectrometry.

The role of analgesic drug metabolites in the formation of lens opacities.

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