Pea d4

Manufactured by Cayman Chemical

Sourced in United States

PEA-d4 is a deuterated form of palmitoylethanolamide (PEA), a fatty acid amide that occurs naturally in the body. It is used as an internal standard in analytical procedures and for research purposes.

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Palmitoylethanolamide-d4 (PEA-d4) (2 citations)

24 protocols using pea d4

Quantification of Endocannabinoids and Metabolites

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OEA, PEA, the deuterated standards D₉-progesterone and D₇-cortisone, and ¹³C-labeled standards ¹³C₃-androstenedione, ¹³C₃-testosterone, and ¹³C₃-progesterone were purchased from Sigma-Aldrich (Buchs, Switzerland). ¹³C₃-cortisol and ¹³C₃-cortisone were purchased from Isoscience (Ambler, USA). AEA, 2-AG, and the deuterated eCBs (D₄-AEA, D₅-2-AG, D₄-OEA, D₄-PEA, and D₁₁-AEA) were purchased from Cayman Chemicals (Ann Arbor, USA). Water and methanol (MeOH) were of LC–MS grade (Chromasolv®) and purchased from Sigma-Aldrich (Buchs SG, Switzerland). Acetone, ethyl acetate, and ammonium fluoride were purchased from Merck (Darmstadt, Germany). Reconstitution solution consisted of 0.2 mM NH₄F in water/methanol 97/3 v/v, respectively. Isolute® SLE + columns were purchased from Biotage® (Uppsala, Sweden). All chemicals were of highest analytical grade.

Restin T., Byland N., Voegel C.D., La Marca-Ghaemmaghami P., Baumgartner M.R., Bassler D., Kraemer T, & Binz T.M. (2022). Endocannabinoid and steroid analysis in infant and adult nails by LC–MS/MS. Analytical and Bioanalytical Chemistry, 414(20), 6201-6211.

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Endocannabinoid Quantification Protocol

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PEA, d₄-PEA, OEA, d₂-OEA, 2-AG, d₅-2-AG, and AMG9810 were from Cayman Chemical (Ann Arbor, MI). AEA and d₄-AEA were from R&D systems. [¹⁴C]AEA (arachidonoyl-[1-¹⁴C]ethanolamide) and rimonabant were provided by the Drug Supply Program at the National Institute on Drug Abuse. GW6471 was purchased from Sigma. All other chemicals were obtained from Fisher Scientific.

Peng X., Studholme K., Kanjiya M.P., Luk J., Bogdan D., Elmes M.W., Carbonetti G., Tong S., Gary Teng Y.H., Rizzo R.C., Li H., Deutsch D.G., Ojima I., Rebecchi M.J., Puopolo M, & Kaczocha M. (2017). Fatty-acid-binding protein inhibition produces analgesic effects through peripheral and central mechanisms. Molecular Pain, 13, 1744806917697007.

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Quantitation of Endocannabinoids in Tissues

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Brain areas and liver were dounce-homogenized and extracted with chloroform/methanol/Tris-HCl (50 mM, pH 7.4) (2:1:1, v/v) containing internal deuterated standards for PEA, OEA, AEA, and 2-AG quantification by isotope dilution (d4-PEA, d4-OEA, d8-AEA and d5-2-AG, Cayman Chemical). The lipid-containing organic phases were then purified by open bed chromatography on silica and aliquots of fractions containing NAEs and monoacylglycerols were analyzed by isotope dilution liquid chromatography/mass spectrometry (LC-MS). MS detection was performed by using values of m/z 304 and 300 (molecular ions + 1 for d4-PEA and PEA), m/z 330 and 326 (molecular ions + 1 for d4-OEA and OEA), m/z 356 and 348 (molecular ions + 1 for d8-AEA and AEA), and 384 and 379 (molecular ion +1 for d5-2-AG and 2-AG). The levels of eCBs were then calculated on the basis of their area ratios with the internal deuterated standard signal areas and their amounts expressed as picomoles were then normalized per gram or milligram of wet tissue.

Giacovazzo G., Bisogno T., Piscitelli F., Verde R., Oddi S., Maccarrone M, & Coccurello R. (2019). Different Routes to Inhibit Fatty Acid Amide Hydrolase: Do All Roads Lead to the Same Place?. International Journal of Molecular Sciences, 20(18), 4503.

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Endocannabinoid Quantification Protocols

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PEA, d₄-PEA, OEA, d₂-OEA, 2-AG and d₅-2-AG were from Cayman Chemical while AEA and d₄-AEA were from R&D systems. [¹⁴C]AEA, rimonabant and SR144528 were obtained from the Drug Supply Program at the National Institute on Drug Abuse. GW6471 was purchased from Sigma while capsazepine was purchased from Cayman Chemical.

Kaczocha M., Glaser S.T., Maher T., Clavin B., Hamilton J., O’Rourke J., Rebecchi M., Puopolo M., Owada Y, & Thanos P.K. (2015). Fatty acid binding protein deletion suppresses inflammatory pain through endocannabinoid/N-acylethanolamine-dependent mechanisms. Molecular Pain, 11, 52.

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Radiolabeled Lipid Signaling Molecules

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12-NBD-stearate [12-N-methyl-(7-nitrobenz-2-oxa-1,3-diazo)aminostearicacid] was from Avanti Polar Lipids (Alabaster, AL). PEA, d₄-PEA, OEA, d₂-OEA, 2-AG and d₅-2-AG were from Cayman Chemical (Ann Arbor, MI). AEA and d₄-AEA were from R&D systems. [¹⁴C]AEA (arachidonoyl-[1-¹⁴C]ethanolamide, 60 mCi/mmol) was provided by the Drug Supply Program at the National Institute on Drug Abuse while [³H]2-oleoylglycerol ([³H]2-OG) was purchased from Perkin Elmer. Acetonitrile, chloroform, and methanol were of the highest possible purity and were obtained from Fisher Scientific.

Kaczocha M., Rebecchi M.J., Ralph B.P., Teng Y.H., Berger W.T., Galbavy W., Elmes M.W., Glaser S.T., Wang L., Rizzo R.C., Deutsch D.G, & Ojima I. (2014). Inhibition of Fatty Acid Binding Proteins Elevates Brain Anandamide Levels and Produces Analgesia. PLoS ONE, 9(4), e94200.

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Pharmacological Compounds for Endocannabinoid Research

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GW6471, AM251, URB937, PF3845, AMC-AEA, LEI-401, PEA, d₄-PEA, OEA, d₂-OEA, 2-AG, and d₅-2-AG were purchased from Cayman Chemical (Ann Arbor, MA). NGF was from Gibco (Waltham. MA). AEA and d₄-AEA were from R&D Systems (Minneapolis, MN). Capsaicin was from Sigma-Aldrich (St. Louis, MO), Fura-2AM and PED-A1 were from Thermo Fisher (Waltham, MA) and Cyclosporin A was from TCI (Portland, OR).

Bogdan D.M., Studholme K., DiBua A., Gordon C., Kanjiya M.P., Yu M., Puopolo M, & Kaczocha M. (2022). FABP5 deletion in nociceptors augments endocannabinoid signaling and suppresses TRPV1 sensitization and inflammatory pain. Scientific Reports, 12, 9241.

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Quantification of Palmitoylethanolamide in Murine Tissues

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Main bronchi and blood were harvested from mice, 15 days after OVA or vehicle administration, and immediately immersed into liquid nitrogen and stored at -80°C until extraction of PEA. PEA was extracted from 100 μL of plasma by liquid–liquid extraction and separated by liquid chromatography (Ultimate 3000 RS, Dionex, CA, United States). Quantitative analyses were performed on a 5500 QTrap^® triple quadrupole/linear ion trap (QqQLIT) mass spectrometer equipped with a TurboIon-Spray TM interface (AB Sciex, Concord, ON, Canada).
Tissues were extracted with chloroform/methanol (2:1, by volume) containing 10 pmol of d4-PEA (provided by Cayman Chemicals, United States). The lipid extracts were purified by silica column chromatography and the fractions containing PEA were analyzed by isotope dilution liquid chromatography–atmospheric pressure chemical ionization mass spectrometry (LC-MS). Results were expressed as picomoles per milligram of tissue (Borrelli et al., 2015 (link)).

Roviezzo F., Rossi A., Caiazzo E., Orlando P., Riemma M.A., Iacono V.M., Guarino A., Ialenti A., Cicala C., Peritore A., Capasso R., Di Marzo V, & Izzo A.A. (2017). Palmitoylethanolamide Supplementation during Sensitization Prevents Airway Allergic Symptoms in the Mouse. Frontiers in Pharmacology, 8, 857.

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Lipid Profiling Using LC-APCI-MS

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First, tissues were dounce-homogenized and extracted with chloroform/methanol/Tris-HCl 50 mM pH 7.4 (2:1:1, v/v) containing internal deuterated standards for AEA, 2-AG, PEA and OEA quantification by isotope dilution (5 pmol of d 8 -AEA, 50 pmol of d 5 -2AG, d 4 -PEA and d 2 -OEA Cayman Chemicals, MI, USA). The lipid-containing organic phase was dried down, weighed and pre-purified by open bed chromatography on silica gel. Fractions were obtained by eluting the column with 99:1, 90:10 and 50:50 (v/v) chloroform/methanol. The 90:10 fraction was used for AEA, 2-AG, PEA and OEA quantification by liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry (LC-APCI-MS), as previously described and using selected ion monitoring at M + 1 values for the four compounds and their deuterated homologues, as described in Piscitelli et al. (2011) (link).

Forner-Piquer I., Mylonas C.C., Calduch-Giner J., Maradonna F., Gioacchini G., Allarà M., Piscitelli F., Di Marzo V., Pérez-Sánchez J, & Carnevali O. (2018). Endocrine disruptors in the diet of male Sparus aurata: Modulation of the endocannabinoid system at the hepatic and central level by Di-isononyl phthalate and Bisphenol A. Environment international, 119.

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Quantification of N-acylethanolamines in Myometrium and Fibroids

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N-acylethanolamine (NAE) concentrations were determined in normal myometrium and fibroids as previously described [19 ]. Briefly, frozen tissues were first pulverized under liquid nitrogen in a pestle and mortar. Approximately 100 mg of pulverized tissue was mixed with deuterated internal standards (12.5 pmol/g AEA-d8 and OEA-d2, and 25 pmol/g PEA-d4, Cayman Chemical, Ann Arbor, MI, USA) and 1 mL phosphoric acid (5%), and thoroughly mixed on a benchtop vortex mixer. The mixture was then diluted with 1 mL deionized water and homogenized for 40 seconds using TissueRuptor (QIAGEN) on ice. The samples were then subjected to centrifugation at 1500 g for 30 minutes at 4°C. The supernatant was carefully transferred to a fresh tube and NAEs extracted by solid phase extraction as described previously [17 (link)]. The extract was dried under a constant stream of nitrogen before being reconstituted in 80 μL of acetonitrile [19 ]. The NAEs were separated and quantified using a previously validated UHPLC-MS/MS method [17 (link),37 (link)].

Ayakannu T., Taylor A.H., Marczylo T.H, & Konje J.C. (2019). New Insights of Uterine Leiomyoma Pathogenesis: Endocannabinoid System. Medical Science Monitor Basic Research, 25, 76-87.

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LC-MS/MS Analysis of Endocannabinoids

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Standards of AEA, 2-AG, PEA, and OEA were obtained from Tocris (Bristol, United Kingdom), AEA-d₄, 2-AG-d₅, PEA-d₄ and OEA-d₄ were from Cayman Chemical (Ann Arbor, MI, USA), acetonitrile and chloroform were from Merck (Darmstadt, Germany), while methanol and formic acid were from POCh (Katowice, Poland). All the stock solutions of the standards, excluding 2-AG and 2-AG-d₅, were prepared in ethanol, whereas 2-AG and 2-AG-d₅ stock solutions were prepared in acetonitrile (concentration 1 mg/mL). All the stock solutions were stored at −80 °C. Further dilutions were prepared using acetonitrile.

Bystrowska B., Frankowska M., Smaga I., Niedzielska-Andres E., Pomierny-Chamioło L, & Filip M. (2019). Cocaine-Induced Reinstatement of Cocaine Seeking Provokes Changes in the Endocannabinoid and N-Acylethanolamine Levels in Rat Brain Structures. Molecules, 24(6), 1125.

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