Studies on 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) and related compounds VII. Quantification of alpha-methylfentanyl metabolites excreted in rat urine.

@article{Sato2010StudiesO1,
  title={Studies on 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) and related compounds VII. Quantification of alpha-methylfentanyl metabolites excreted in rat urine.},
  author={Shinichi Sato and Shin'ichi Suzuki and Xiao-Pen Lee and Keizo Sato},
  journal={Forensic science international},
  year={2010},
  volume={195 1-3},
  pages={
          68-72
        }
}

Figures and Tables from this paper

Studies on 1-(2-Phenethyl)-4-(N-Propionylanilino)Piperidine (Fentanyl) and Its Related Compounds: Novel Metabolites in Rat Urine Following Injection of α-Methylfentanyl, One of the Most Abused Typical Designer Drugs

Four novel metabolites, which reflect the original structure of α-methylfentanyl, were identified in rat urine, and were identified by comparisons of their retention times and mass spectra obtained by gas chromatography-mass spectrometry (GC/MS) and mass chromatography of mono- and di-hydroxy α- methylf fentanyl with those of the synthesized authentic compounds.

Studies on the in vitro and in vivo metabolism of the synthetic opioids U-51754, U-47931E, and methoxyacetylfentanyl using hyphenated high-resolution mass spectrometry

In general, metabolite formation was comparable in vitro and in vivo, but fewer metabolites, particularly those after multiple reaction steps and phase II conjugates, were found in phS9, consistent with those of comparable compounds obtained from human liver microsomes, human hepatocytes, and/or human case studies.

Determination of Fentanyl, Alpha-Methylfentanyl, Beta-Hydroxyfentanyl, and the Metabolite Norfentanyl in Rat Urine by LC-MS/MS.

The results showed that both alpha-methylfentanyl and beta-hydroxyfentanyl were predominantly metabolized into norfentanyl in HLM and RLM, indicating that norf fentanyl has a higher concentration in rat urine and was detectable for at least three days after exposure to these compounds.

Identification and physicochemical characterization of 4-fluorobutyrfentanyl (1-((4-fluorophenyl)(1-phenethylpiperidin-4-yl)amino)butan-1-one, 4-FBF) in seized materials and post-mortem biological samples.

The first two analytically confirmed cases of fatal intoxication associated with 4-FBF are presented, including a 26-year-old male drug user who was found dead at home and a 25- year-old female, occasional user of NPS and drugs, who was also founddead at home.

Metabolism of designer drugs of abuse: an updated review.

The metabolism of new designer drugs of abuse that have emerged on the black market during the last years and the cytochrome P450 or monoamineoxidase isoenzyme-dependent metabolism are reviewed.

Metabolic Pathways and Potencies of New Fentanyl Analogs

A review on the metabolic profiles of new fentanyl analogs responsible for a growing number of severe and fatal intoxications in the United States, Europe, Canada, Australia, and Japan in the last years, as assessed by a systematic search of the scientific literature and official reports.

Metabolism of 4-Aminopiperidine Drugs by Cytochrome P450s: Molecular and Quantum Mechanical Insights into Drug Design

It is suggested that the molecular interactions between substrates and CYP3A4 active site residues are essential for the N-dealkylation of 4-aminopiperidines and structure-based drug design approaches look promising to guide drug discovery programs into the optimized drug metabolism space.

Extension of the Temporal Window for the Determination of Alpha-Methylthiofentanyl and Thiofentanyl in Rat Urine by Monitoring the Metabolite Norfentanyl Using Online Solid-Phase Extraction (SPE) Coupled with Ultra-High Performance Liquid Chromatography–Tandem Mass Spectrometry (UHPLC–MS/MS)

Abstract Alpha-methylthiofentanyl and thiofentanyl are psychoactive substances that have been abused in recent years, strongly threatening social and public security. Because they are rapidly

Identification and analytical properties of acetyl fentanyl metabolites

Acetyl fentanyl is a novel designer drug substance, a derivative of fentanyl. Its major metabolites were identified in samples of urine from consumers of acetyl fentanyl using gas chromatography and

New synthetic opioid cyclopropylfentanyl together with other novel synthetic opioids in respiratory insufficient comatose patients detected by toxicological analysis

In cases of intoxication without a medical history, the detailed toxicological analysis may reveal new psychoactive substances which are not detected by standard toxicological screening approaches.

References

SHOWING 1-10 OF 33 REFERENCES

Studies on 1-(2-Phenethyl)-4-(N-Propionylanilino)Piperidine (Fentanyl) and Its Related Compounds: Novel Metabolites in Rat Urine Following Injection of α-Methylfentanyl, One of the Most Abused Typical Designer Drugs

Four novel metabolites, which reflect the original structure of α-methylfentanyl, were identified in rat urine, and were identified by comparisons of their retention times and mass spectra obtained by gas chromatography-mass spectrometry (GC/MS) and mass chromatography of mono- and di-hydroxy α- methylf fentanyl with those of the synthesized authentic compounds.

Studies on 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) and its related compounds. VI. Structure-analgesic activity relationship for fentanyl, methyl-substituted fentanyls and other analogues

3-Methylfentanyl showed the strongest analgesic activity among these compounds, and the most frequently abused fentanyl derivative, α-methylf fentanyl, also showed quite strong activity.

N-4-Substituted 1-(2-arylethyl)-4-piperidinyl-N-phenylpropanamides, a novel series of extremely potent analgesics with unusually high safety margin.

R 30 730 has a rapid onset of action and is 4521 times more potent than morphine at the time of peak effect; it has a relatively short duration of action comparable to that of fentanyl and its safety margin is unusually high.

Identification of fentanyl metabolites in rat urine by gas chromatography-mass spectrometry with stable-isotope tracers.

The metabolites of fentanyl (l), which has been widely used as a neuroleptic analgesic agent, were identified in urine of rats by gas chromatography-mass spectrometry combined with a stable-isotope

Synthetic analgesics. Synthesis and pharmacology of the diastereoisomers of N-(3-methyl-1-(2-phenylethyl)-4-piperidyl)-N-phenylpropanamide and N-(3-methyl-1-(1-methyl-2-phenylethyl)-4-piperidyl)-N-phenylpropanamide.

The synthesis of the respective diastereoisomers and enantiomers of N-[3-methyl-1-(2-phenylethyl)-4-piperidylj-Nphenylpropanamide and N-phenyl Propanamide is reported, which are found to be an extremely potent analgesic, up to 6684 times morphine.

3‐Allyl analogues of fentanyl

Data on the effects of 3-substitution so far available support the view of fentanyl and pethidine-related analgesics sharing common drugreceptor association modes, and results on studies of phenolic analogues of the two series further corroborate this argument.

Synthesis and evaluation of 1- and 2-substituted fentanyl analogues for opioid activity.

Results of synthesized fentanyl analogues suggest that fentanyl and the opioid peptides interact with different subsites on either mu or sigma receptors, and studies using the irreversible mu opioid receptor antagonist, beta-funaltrexamine, indicate that fentanyl interacts preferentially with mu opioid receptors.

Conformationally restrained fentanyl analogues. 2. Synthesis and analgetic evaluation of perhydro-1,6-naphthyridin-2-ones.

Conformational flexibility of the N-acyl portion of fentanyl-type analgetics was restricted through the synthesis of novel perhydro-1,6-naphthyridin-2-one derivatives, reaffirming the sensitivity of this portion of 4-anilidopiperidine anal getics to conformational restraint.

Studies on fentanyl and related compounds IV. Chromatographic and spectrometric discrimination of fentanyl and its derivatives.

Chromatographic and spectrometric discrimination of fentanyl and its 24 analogues are discussed, and the combination of GC and mass spectrometry enabled discrimination of all 25 samples.