Acetyl fentanyl

Manufactured by Cayman Chemical

Sourced in United States

Acetyl fentanyl is a synthetic opioid compound. It is a structural analogue of the pharmaceutical drug fentanyl. Acetyl fentanyl can be used in research applications involving the study of opioid pharmacology and toxicology.

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8 protocols using acetyl fentanyl

Opioid Analytics in Human Samples

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Mepirapim hydrochloride, acetyl fentanyl, and acetyl fentanyl-d₅ were purchased from Cayman Chemical (Ann Arbor, MI, USA). Other common chemicals used in this study were of the highest purity commercially available.
To prepare the calibrators and quality controls, we collected human whole blood and urine from two healthy volunteers with no known diseases and no history of drug use. Informed consent was obtained from both participants who supplied blood and urine for use as blank matrices. The samples obtained in December 2013 were stored at −80 °C until analysis.

Mochizuki A., Nakazawa H., Adachi N., Takekawa K, & Shojo H. (2017). Identification and quantification of mepirapim and acetyl fentanyl in authentic human whole blood and urine samples by GC–MS/MS and LC–MS/MS. Forensic Toxicology, 36(1), 81-87.

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Analytical Standards for Opioid Detection

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Carfentanil, cocaine, fentanyl, heroin, oxycodone, and remifentanil were purchased as analytical standards (100 μg/mL diluted in methanol) from Cerilliant Corporation (Round Rock, TX). Acetyl fentanyl, butyryl fentanyl, crotonyl fentanyl, cyclopropyl fentanyl, p-fluoroisobutyryl fentanyl (FIBF), 2-furanyl fentanyl, β-hydroxythiol fentanyl, methoxy fentanyl, methyl fentanyl, norfentanyl, and U-47700 were purchased as analytical standards (100 μg/mL diluted in methanol) from Cayman Chemical (Ann Arbor, MI). A complete list of test compounds used in this study is shown in Table 1.

Angelini D.J., Biggs T.D., Maughan M.N., Feasel M.G., Sisco E, & Sekowski J.W. (2019). Evaluation of a lateral flow immunoassay for the detection of the synthetic opioid fentanyl. Forensic science international, 300, 75-81.

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Quantitative Analysis of Synthetic Opioids

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Standard of acetylfentanyl (hydrochloride), acrylfentanyl (hydrochloride), alfentanil (hydrochloride), butyrylfentanyl, carfentanyl, (±)-cis-3-methylfentanyl (hydrochloride), (±)-cis-3-methylthiofentanyl (hydrochloride), fentanyl (hydrochloride), furanylfentanyl (hydrochloride), α-methylfentanyl (hydrochloride), α-methylthiofentanyl (hydrochloride), β-hydroxyfentanyl (hydrochloride), ortho-fluorofentanyl (hydrochloride), ocfentanyl, para-fluorofentanyl (hydrochloride), remifentanyl (hydrochloride), sufentanyl, 4-ANPP, norfentanyl, butyrylfentanyl carboxy metabolite, despropionylpara-fluorofentanyl, (±)-trans-3-methyl norfentanyl, methoxyacetyl norfentanyl (hydrochloride), valerylfentanyl carboxy metabolite, morphine, methadone, EDDP, 6-MAM, codeine, MT-45, fentanyl-d5 (hydrochloride) and nordentanyl-d5 were purchased from Cayman Chemical (Ann Arbor, MI, USA) in form of methanolic solution at the concentration of 1 mg mL⁻¹. Working solutions were prepared at the concentration of 1 μg mL⁻¹ and stored at −20 °C. Water, methanol, acetonitrile and 2-propanol were obtained from Carlo Erba (Milano, Italia) while sodium carbonate, sodium bicarbonate and ammonium formate were purchased from Sigma-Aldrich (Milwaukee, WI, USA).

Vincenti F., Montesano C., Pirau S., Gregori A., Di Rosa F., Curini R, & Sergi M. (2021). Simultaneous Quantification of 25 Fentanyl Derivatives and Metabolites in Oral Fluid by Means of Microextraction on Packed Sorbent and LC–HRMS/MS Analysis. Molecules, 26(19), 5870.

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Novel Synthetic Opioid Quantification

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Mepirapim hydrochloride, acetyl fentanyl, JWH-200 and acetyl fentanyl-d₅ were purchased from Cayman Chemical (Ann Arbor, MI, USA), and Isolute SLE + (1 mL capacity) columns from Biotage (Uppsala, Sweden). Other common chemicals used in this study were of the highest purity commercially available.

Mochizuki A., Nakazawa H., Adachi N., Takekawa K, & Shojo H. (2018). Postmortem distribution of mepirapim and acetyl fentanyl in biological fluid and solid tissue specimens measured by the standard addition method. Forensic Toxicology, 37(1), 27-33.

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Quantitative Determination of Fentanyl Analogs

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Working standards (acetylfentanyl, acetyl norfentanyl, alfentanil, butyrylfentanyl, butyrylfentanyl carboxy metabolite, butyryl norfentanyl, carfentanil, cyclopropylfentanyl, cyclopropyl norfentanyl, 4-ANPP, despropionyl para-fluorofentanyl, fentanyl, furanylfentanyl, furanyl norfentanyl, furanylethyl fentanyl, β-hydroxyfentanyl, β-hydroxythiofentanyl, methoxyacetylfentanyl, methoxyacetyl norfentanyl, norfentanyl, phenylacetyl fentanyl, sufentanil, and valerylfentanyl carboxy metabolite) and deuterated internal standards (IS; acetyl norfentanyl-D5 and fentanyl-D5) were purchased from Cayman Chemical (Ann Arbor, MI, USA) and stored at −20°C until use. LC-MS grade water, acetonitrile, methanol, and formic acid and LC grade acetone and dichloromethane were obtained from Sigma-Aldrich® (Milano, Italy). Ammonium acetate buffer was prepared with ≥97% purity ammonium acetate salt (Sigma-Aldrich®) dissolved in LC-MS water. VMA-T M3®, Washing Solution, and Multimatrix Eluent were acquired from Comedical® s.r.l. (Trento, Italy); their composition is not disclosed.

Busardò F.P., Carlier J., Giorgetti R., Tagliabracci A., Pacifici R., Gottardi M, & Pichini S. (2019). Ultra-High-Performance Liquid Chromatography-Tandem Mass Spectrometry Assay for Quantifying Fentanyl and 22 Analogs and Metabolites in Whole Blood, Urine, and Hair. Frontiers in Chemistry, 7, 184.

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Opioid and Synthetic Opioid Separations

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The run buffer used for opioid and synthetic opioid separations was 12 mmol/L acetic acid, 3.3 mmol/L ammonium acetate pH 4.4 (Sigma-Aldrich, St. Louis, MO, USA) in ultrapure water (Millipore Milli-Q, 18.0 MΩ-cm). Acetaminophen, caffeine, mannitol, procaine, quinine, and methanol were all purchased from Sigma-Aldrich (St. Louis, MO, USA).
All fentanyl analogues (acetyl fentanyl, acryl fentanyl, benzyl fentanyl, butyryl fentanyl, furanyl fentanyl, methacryl fentanyl, methoxyacetyl fentanyl, phenyl fentanyl, valeryl fentanyl) were purchased as hydrochloride salts from Cayman Chemical (Ann Arbor, MI, USA) or, when possible, as 1 mg·mL⁻¹ methanolic solutions. Powdered standards and samples were dissolved gravimetrically in methanol (Sigma-Aldrich, St. Louis, MO). The remaining opioids and narcotics (heroin, fentanyl, cocaine, U-47700) were purchased as 1 mg·mL⁻¹ solutions in methanol or acetonitrile from Cerilliant (Round Rock, TX, USA). All sample dilutions were prepared in run buffer, and methanol was added as necessary to allow for a constant 4 % by volume organic solvent across all analyses. When increased analyte concentrations were desired, standards were concentrated to assure each sample contained a maximum of 4 % (v/v) solvent.

Krauss S.T., Ross D, & Forbes T.P. (2019). Separation and detection of trace fentanyl from complex mixtures using gradient elution moving boundary electrophoresis.. Analytical chemistry, 91(20), 13014-13021.

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Quantification of Novel Fentanyl Analogs

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Acetylfentanyl, acrylfentanyl, furanylfentanyl and 4-fluoro-isobutyrylfentanyl were purchased as powders from Cayman Chemical (Ann Arbor, USA), diclofenac from Sigma (Stockholm, Sweden). Cryopreserved hepatocytes LiverPool (10-donor-pool), InVitro Gro HT and InVitro Gro KHB media were obtained from Bioreclamation IVT (Brussels, Belgium). Liquid chromatography mass spectrometry grade acetonitrile, water, methanol and formic acid were from Fisher Scientific (Gothenburg, Sweden), ammonium formate from Fluka (Sigma-Aldrich, Stockholm, Sweden), ammonium acetate and acetic acid from Merck (Darmstadt, Germany). The βglucuronidase/sulfatase mixture (Helix pomatia) was purchased from Roche (Mannheim, Germany). Ultra-pure water was prepared in-house using a MilliQ Gradient 10 production unit (Millipore, Billerica, USA).

Watanabe S., Vikingsson S., Roman M., Green H., Kronstrand R, & Wohlfarth A. (2017). In Vitro and In Vivo Metabolite Identification Studies for the New Synthetic Opioids Acetylfentanyl, Acrylfentanyl, Furanylfentanyl, and 4-Fluoro-Isobutyrylfentanyl. The AAPS journal, 19(4).

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Sourcing and Characterization of Fentanyl Analogues

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Fentanyl, 4-ANPP, Valeryl Fentanyl, Furanyl Fentanyl, Methoxyacetyl Fentanyl, Acetyl Fentanyl, Acryl Fentanyl, and 2′-fluoro ortho-FluoroFentanyl were purchased from Cayman Chemical Company (Ann Arbor, MI). Perchloric acid was obtained from Fisher Scientific (Fair Lawn, NJ). Potassium chloride was received from Sigma-Aldrich (St. Louis, MO). Water (18.2 MΩ) was obtained using a Millipore Direct-Q ® UV water purification system (Billerica, MA).

Ott C.E., Perez-Estebañez M., Hernandez S., Kelly K., Dalzell K.A., Arcos‐Martínez M.J., Heras A., Colina Á., & Arroyo‐Mora L.E. (2022). Forensic Identification of Fentanyl and its Analogs by Electrochemical-Surface Enhanced Raman Spectroscopy (EC-SERS) for the Screening of Seized Drugs of Abuse. Frontiers in Analytical Science, 2.

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