Identification and Quantitative Determination of Fentanyl Metabolites in Patients by Gas Chromatography-Mass Spectrometry

Goromaru, Tsuyoshi; Mizunuma, Hiroshi; Yoshimura, Natsue; Miyawaki, Takenori; Sameshima, T.; Miyao, J; Furuta, Takahisa; Baba, Shigeo

doi:10.1097/00000542-198407000-00013

Cited by 70 publications

(38 citation statements)

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“…In all previous reports regarding the metabolism of fentanyl, [11][12][13][15][16][17][18] the major metabolite was nor-fentanyl (M1), furthermore, other metabolites of ω position hydroxypropionyl nor-fentanyl (ω hydroxy nor-fentanyl, M2) and ω hydroxyfentanyl were also reported. [11][12][13] With the exception of ω hydroxyfentanyl, metabolites that preserved the original structure of fentanyl were not reported.…”

Section: Gc/ms and Mass Chromatography For Detection Of Metabolites Wmentioning

confidence: 90%

“…[11][12][13] With the exception of ω hydroxyfentanyl, metabolites that preserved the original structure of fentanyl were not reported. The structures of major metabolites, such as, norfentanyl and ω hydroxy nor-fentanyl are also summarized in Fig.…”

Section: Gc/ms and Mass Chromatography For Detection Of Metabolites Wmentioning

confidence: 99%

“…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. 1.…”

Section: Introductionmentioning

confidence: 99%

“…Similar to the case for methamphetamine, analysis of urine or blood should be performed to detect fentanyl metabolites that have the same structure as the original abused drug. There are many published papers regarding the metabolism of fentanyl itself, [11][12][13][15][16][17][18] and recent enzymatic studies of fentanyl have involved human hepatocytes and P-450 3A4. 19,20) However, none of these reports except one, ω position hydroxypropionylfentanyl (ω hydroxyfentanyl), have not focused on metabolites that reflect the structure of the dosed compound.…”

Section: Introductionmentioning

confidence: 99%

“…19,20) However, none of these reports except one, ω position hydroxypropionylfentanyl (ω hydroxyfentanyl), have not focused on metabolites that reflect the structure of the dosed compound. [11][12][13] The metabolites of fentanyl are shown in Fig. 2.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

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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