Studies on 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) and related compounds. I. Spectrometric and chromatographic analyses of 3-methylfentanyl and .ALPHA.-methylfentanyl.

Suzuki, Shinichi; Inoue, Takako; Kashima, Choji

doi:10.1248/cpb.34.1340

Cited by 20 publications

(14 citation statements)

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“…The fragmentation of fentanyls has been described in detail previously. 5,13,30 Mixtures of all nine amphetamines were analysed by both AP-DIOS-MS/MS and AP-MALDI-MS/MS to determine the applicability of the techniques in the unequivocal identification of a single analyte in a sample, including several compounds of the same type. The protonated molecules of the compounds (Figs 1(a) and 2(a)) were isolated automatically in sequence and fragmented by MS/MS during one run from one spot.…”

Section: Resultsmentioning

confidence: 99%

Analysis of amphetamines and fentanyls by atmospheric pressure desorption/ionization on silicon mass spectrometry and matrix‐assisted laser desorption/ionization mass spectrometry and its application to forensic analysis of drug seizures

Pihlainen

Grigoras²,

Franssila³

et al. 2005

J. Mass Spectrom.

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The suitability of atmospheric pressure desorption/ionization on silicon mass spectrometry (AP-DIOS-MS) and matrix-assisted laser desorption ionization mass spectrometry (AP-MALDI-MS) for the identification of amphetamines and fentanyls in forensic samples was studied. With both ionization techniques, the mass spectra recorded showed abundant protonated molecules, and the background did not disturb the analysis. The use of tandem mass spectrometry (MS/MS) allowed unambiguous identification of the amphetamines and fentanyls. AP-DIOS-MS/MS and AP-MALDI-MS/MS were also successfully applied to the identification of authentic compounds from drug seizures. Common diluents and tablet materials did not disturb the analysis and compounds were unequivocally identified. The limits of detection (LODs) for amphetamines and fentanyls with AP-DIOS-MS/MS were 1-3 pmol, indicating excellent sensitivity of the method. The LODs with AP-MALDI-MS/MS were about 5-10 times higher.

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Section: Resultsmentioning

confidence: 99%

Analysis of amphetamines and fentanyls by atmospheric pressure desorption/ionization on silicon mass spectrometry and matrix‐assisted laser desorption/ionization mass spectrometry and its application to forensic analysis of drug seizures

Pihlainen

Grigoras²,

Franssila³

et al. 2005

J. Mass Spectrom.

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“…Fentanyl analogues with a methyl group (e.g., α-methyl, 3-methyl, p-methyl, n-butyryl, and isobutyryl) were synthesized in accordance with previous reports [6,7,[10][11][12][13][14][15].…”

Section: Synthesis Of Fentanyl Analoguesmentioning

confidence: 98%

“…After investigation by instrumental analysis, including nuclear magnetic resonance spectroscopy and mass spectrometry, its structure was determined to be 3-methylfentanyl (3) [4,5]. In addition, comparison of the reported mass spectra of synthesized 3-methylfentanyl with those of other mono-methylated fentanyl analogues proved that the structure of the most widely abused drug was α-methylfentanyl (2) [7]. These compounds had high potential for abuse, because of their ease of synthesis and high analgesic activity.…”

Section: Introductionmentioning

confidence: 99%

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

2008

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“…In a previous study, the reported mass spectrum of bogus "China White" was compared with those of synthesized fentanyls, and reported structure of bogus "China White" was presumed to involve the introduction of a methyl group to the α-position of the phenethyl group of fentanyl (α-methylfentanyl). 7) Furthermore, several discrimination methods for fentanyl and its analogues have been reported. [8][9][10][11][12][13] The structures of fentanyl, 3-methylfentanyl and α-methylfentanyl are shown in Fig.…”

Section: Introductionmentioning

confidence: 99%

“…3. 7) Other chemicals were of analytical grade and the water used was prepared with a Milli-Q system (Nihon Millipore Inc., Tokyo, Japan). Animal and Urine Samples --Male Wistar rats (120-150 g) were used in this study.…”

Section: Introductionmentioning

confidence: 99%

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

Higashikawa

Suzuki

2008

JOURNAL OF HEALTH SCIENCE

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Although 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) is controlled by drug control laws, its slightly modified compounds, which show the same analgesic activities, cannot be controlled legally. Among these fentanyl analogues, 1-[2-(2-methylphenethyl)]-4-(N-propionylanilino)piperidine (α-methylfentanyl) is the typical and most widely abused drug and its overdose has caused a number of fatalities. Analysis of the urine of addicts has been widely performed to detect its metabolites and the unchanged compound for proof of its abuse. In this case, the metabolites detected in urine should reflect the structure of the original compound. In the present report, for clarification of α-methylfentanyl abuse, four novel metabolites, which reflect the original structure of α-methylfentanyl, were identified in rat urine. One of these was the p-hydroxy form of the aromatic ring of the α-methylfentanyl phenethyl group (mono-aromatic hydroxy α-methylfentanyl), while the second and third ones were metabolites of ω-1 or ω position hydroxypropionyl of α-methylfentanyl (mono-hydroxypropionyl α-methylfentanyl). The fourth one was a metabolite involving the p-hydroxy form of the aromatic ring of the phenethyl group and ω position of hydroxypropionyl α-methylfentanyl (di-hydroxy α-methylfentanyl). The structures of these compounds 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-methylfentanyl with those of the synthesized authentic compounds.

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Studies on 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) and related compounds. I. Spectrometric and chromatographic analyses of 3-methylfentanyl and .ALPHA.-methylfentanyl.

Cited by 20 publications

References 0 publications

Analysis of amphetamines and fentanyls by atmospheric pressure desorption/ionization on silicon mass spectrometry and matrix‐assisted laser desorption/ionization mass spectrometry and its application to forensic analysis of drug seizures

Analysis of amphetamines and fentanyls by atmospheric pressure desorption/ionization on silicon mass spectrometry and matrix‐assisted laser desorption/ionization mass spectrometry and its application to forensic analysis of drug seizures

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

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

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