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Anandamide

Anandamide is a naturally occurring endogenous cannabinoid neurotransmitter found in the mammalian brain and other tissues.
It binds to and activates the same receptors as delta-9-tetrahydrocannabinol, the psychoactive component in cannabis.
Anandamide plays a role in pain perception, emotion, and memory, and has been implicated in a variety of physiological and pathological processes.
It's chemical structure is N-arachindoylethanolamie.
Reasearch on anandamide is optimized by PubCompare.ai, which helps users find the most accurate and reproducible protocols from scientific literature, pre-prints, and patents to enhance research efficiency and reliability.

Most cited protocols related to «Anandamide»

1
Quantification of Endocannabinoids and Precursors
Quantification of endogenous NAEs and 2-AG were performed as previously described with minor modifications [30] (link). Mice were rapidly euthanized by decapitation and their brains flash frozen in liquid nitrogen. The brains were subsequently thawed, weighed, and homogenized in 8 ml of 2∶1∶1 CHCl3:MeOH:Tris (50 mM, pH 8) in the presence of 4 ng d4-PEA, 4 ng d2-OEA, 400 pg d4-AEA, and 40 ng d5-2-AG. Following centrifugation at 4°C, the organic layer was removed and brought up to 8 ml with the same buffer and centrifuged again. The resulting organic layer was dried down with argon and resuspended with 100 μl of 2∶1 CHCl3:MeOH and 10 μl was injected into the Thermo TSQ Quantum Access Triple Quadropole mass spectrometer. LC separation was achieved on a Gemini C18 (50×2 mm×5 μm) equipped with a Gemini C18 SecurityGuard precolumn (4 mm length ×2 mm internal diameter). Mobile phase A consisted of 95∶5% v:v H20:MeOH while mobile phase B was composed of 60∶35∶5 v:v:v i-PrOH:MeOH:H2O and quantification was performed in the positive ion mode with the voltage set at 4 kV. 0.1% formic acid was added to assist in ionization. The sheath pressure was 30 and the capillary was set at 270 °C. The flow rate was 100 μl/min. The gradient started at 0% B and increased to 100% B over 15 min followed by an isocratic gradient of 100% B for 10 min, and was equilibrated for 15 min at 0% B.
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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Publication 2014
Argon Brain Buffers Capillaries Centrifugation Chloroform Decapitation formic acid Freezing Mice, Laboratory Nitrogen Pressure Tromethamine
2
Western Blot Analysis of Hippocampus Protein Fractions
For Western blot analysis, 0, 30 and 60 min after the vehicle or URB597 administration, male mice were sacrificed by decapitation, hippocampus was dissected, flash frozen and stored at −80°C. Tissue homogenates from the hippocampus containing freshly added 1% protease inhibitor mixture (Roche, Indianapolis, IN, USA) and phosphatase inhibitors were centrifuged at 7700 g for 1 min, and the supernatant (total extract) was aspirated and stored at −80°C until use. The pellet (nuclear fraction) was then resuspended in a nuclear extraction buffer (Grabowski, 2005 (link)) and nuclear fraction was prepared as described before (Basavarajappa and Subbanna, 2014 (link)). The supernatant was used to prepare plasma membrane (PM) fractions as described before (Basavarajappa et al., 1998 (link); Basavarajappa and Hungund, 1999 (link); Basavarajappa et al., 2006 (link); Subbanna et al., 2013 ). The nuclear and PM fractions were stored at −80°C until use. The samples were prepared in a sample buffer as previously described by our laboratory (Basavarajappa et al., 2008 (link); Subbanna et al., 2013 ). The blots were incubated in primary antibody; anti-rabbit-CB1R (0.1μg/ml, Thermo Scientific, Waltham, MA), anti-mouse CaMKIV (Sc-55501, 1: 1000), anti-rabbit pCaMKIV (Sc-28443-R, 1: 1000) (Santa Cruz Biotechnology, Santa Cruz, CA, USA), anti-rabbit p44/42 MAPK (ERK1/2) (# 9102, 1:2000), anti-rabbit-phospho-p44/42 MAPK (# 9101, 1:1000), anti-mouse-β-actin (#3700, 1:1000, Cell Signaling Technology, Danvers, MA, USA), anti-mouse-pCREB (Ser133) (# 05-807, 1:1000) and anti-rabbit-CREB (# 04-218, 1:1000) (Millipore, Billerica, MA, USA) for 3 h at room temperature or overnight at 4°C and processed as previously described by our laboratory (Basavarajappa et al., 2008 (link)).
Basavarajappa B.S., Nagre N.N., Xie S, & Subbanna S. (2014). Elevation of Endogenous Anandamide Impairs LTP, Learning and Memory through CB1 Receptor Signaling in Mice. Hippocampus, 24(7), 808-818.
Publication 2014
Actins Buffers Decapitation Freezing Immunoglobulins inhibitors Males Mice, House Mitogen-Activated Protein Kinase 3 Phosphoric Monoester Hydrolases Plasma Membrane Protease Inhibitors Rabbits Seahorses Tissues URB 597 Western Blot
3
Cannabidiol vs Amisulpride in Schizophrenia
This study was a therapeutic-exploratory (phase II), double-blinded, monocenter, randomized, parallel-group, controlled clinical trial of cannabidiol vs amisulpride (CBD-CT1; ClinicalTrials.gov. Identifier: NCT00628290). The study protocol was approved by the Ethics Committee of the University of Cologne and the BfArM (Federal Institute for Drugs and Medical Products). Initially an independent psychiatrist assessed patients to confirm their ability to provide informed consent. Then, written informed consent was obtained from each patient following a detailed explanation of study procedures.
Men and women age 18–50 years who had a diagnosis of schizophrenia or schizophreniform psychosis according to the DSM-IV criteria were eligible for the study. All patients were hospitalized at baseline and through day 28 after random assignment to treatment. A total number of 42 inpatients of the Department of Psychiatry and Psychotherapy of the University of Cologne participated in the study. In all, 37 patients were suffering from acute paranoid schizophrenia (DSM-IV 295.30). Another 5 patients were initially diagnosed as suffering from schizophreniform psychosis (DSM-IV 295.40) based on the duration of illness, but were followed-up and diagnosed with paranoid schizophrenia after completing the study. Only acutely psychotic patients with a total Brief Psychiatric Rating Scale (BPRS) score ⩾36 and a BPRS THOT factor (thought disorders) score ⩾12 were eligible to participate. Patients with a positive urine drug screening for illicit drugs in general and cannabinoids in particular were not allowed to participate to avoid an interaction of currently bioactive cannabinoids (including cannabidiol) with treatment. Further exclusion criteria were relevant psychiatric disorders including substance use disorders, previous treatment with a depot antipsychotic within 3 months before the participation in the study, a history of treatment resistance, defined by the persistence of severe symptoms despite adequate treatment with at least two antipsychotics or prior treatment with clozapine, a relevant and/or unstable medical condition and an insufficient contraception, pregnancy or breast-feeding in female patients.
We enrolled 42 acutely exacerbated schizophrenic patients who had met the DSM-IV criteria. In all, 39 patients were evaluated according to modified intention-to-treat (Table 1), 33 were observed and treated per protocol and all 42 were valid for safety evaluation (Figure 1). After a screening period of up to 7 days and a minimum period of 3 antipsychotic-free days patients were randomized (1:1) to receive either cannabidiol or amisulpride starting with 200 mg per day each and increased stepwise by 200 mg per day to a daily dose of 200 mg four times daily (total 800 mg per day) each within the first week. The hospital pharmacy provided individual medication kits according to a randomization sequence prepared by a person otherwise not involved in the study (drawing paper lots out of a bowl). The respective treatment was maintained for another 3 weeks. A reduction of each treatment to 600 mg per day was allowed for clinical reasons, such as unwanted side effects after week 2, which was the case for three patients in the cannabidiol and five patients in the amisulpride treatment group. In addition, lorazepam co-medication was allowed with up to 7.5 mg per day during the entire study.
Leweke F.M., Piomelli D., Pahlisch F., Muhl D., Gerth C.W., Hoyer C., Klosterkötter J., Hellmich M, & Koethe D. (2012). Cannabidiol enhances anandamide signaling and alleviates psychotic symptoms of schizophrenia. Translational Psychiatry, 2(3), e94-.
Publication 2012
4
Cannabinoid-induced paw tremors assessment
Subjects (n=36) were treated with vehicle, AEA, or Δ9-THC according to the repeated administration schedule described above. On Day 6, mice were injected with the final subchronic treatment, and placed in a Plexiglas observation chamber (21.5 × 21.5 × 15 cm). Thirty min later, subjects were administered rimonabant (10mg/kg; i.p.) and scored for paw tremors (shaking of one or both paws) and head shaking/twitching (minimum of two quick, successive head movements in a counterclockwise/clockwise fashion and righted to the original position). Mice were observed for 1 h and scored in 5- min bins, separated by 5-min break periods.
Falenski K.W., Thorpe A.J., Schlosburg J.E., Cravatt B.F., Abdullah R.A., Smith T.H., Selley D.E., Lichtman A.H, & Sim-Selley L.J. (2010). FAAH−/− Mice Display Differential Tolerance, Dependence, and Cannabinoid Receptor Adaptation After Δ9-Tetrahydrocannabinol and Anandamide Administration. Neuropsychopharmacology, 35(8), 1775-1787.
Publication 2010
Head Head Movements Mice, House Plexiglas Rimonabant Treatment Protocols
5
Dose-Response Evaluation of THC and AEA
Twenty-four h after the final subchronic injection, a cumulative dosing regimen was employed to determine the dose-response relationships for antinociception, hypothermia, and hypomotility. Subjects received increasing doses of THC or AEA every 40 min with endpoints assessed 30 min after each injection, as specified in the results. Several experiments were conducted that included control mice that received repeated vehicle injections every 40 min, with endpoints assessed 30 min to ensure that no vehicle effects occurred.
Falenski K.W., Thorpe A.J., Schlosburg J.E., Cravatt B.F., Abdullah R.A., Smith T.H., Selley D.E., Lichtman A.H, & Sim-Selley L.J. (2010). FAAH−/− Mice Display Differential Tolerance, Dependence, and Cannabinoid Receptor Adaptation After Δ9-Tetrahydrocannabinol and Anandamide Administration. Neuropsychopharmacology, 35(8), 1775-1787.
Publication 2010
Mus Treatment Protocols

Most recents protocols related to «Anandamide»

1
Synthesis of Anandamide and ACEA Compounds
Anandamide and ACEA were synthesized as described previously [50 (link)]. In short, anandamide (AEA) and chloro-anandamide (ACEA, (5Z,8Z,11Z,14Z)-N-(2-chloroethyl)icosa-5,8,11,14-tetraenamide) were synthesized from arachidonic acid and ethanolamine or 2-chloroethylamine, respectively, after activation of the carboxyl group of arachidonic acid with isobutyl chloroformate in the presence of triethylamine. AEA’s physico-chemical constants were in accordance with published data. For ACEA: 1H-NMR (δ, CDCl3: 0.902 [3H, H20], 1.313 [8H, H19,18,17,16], 1.745 [3H, H3], 2.080 [4H, H4], 2.232 [2H, H2], 2.825 [6H, H7,10,13,], 2.633 [4H, H 2’, 1’], 5.387 [8H, -CH=CH-], 5.852[1H, NH]. ESI MS m/z (C22H36ClNO, exact mass: 365.2485): 366.2335 [M+H]+, 388.2335 [M+Na]+, 404.2061 [M+K]+
Akimov M.G., Gretskaya N.M., Gorbacheva E.I., Khadour N., Chernavskaya V.S., Sherstyanykh G.D., Kovaleko T.F., Fomina-Ageeva E.V, & Bezuglov V.V. (2024). The Interaction of the Endocannabinoid Anandamide and Paracannabinoid Lysophosphatidylinositol during Cell Death Induction in Human Breast Cancer Cells. International Journal of Molecular Sciences, 25(4), 2271.
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Publication 2024
2
Cannabinoid Compound Characterization
Not available on PMC !
All the chemicals and reagents were obtained from Fisher Scienti c (Fair Lawn, NJ, USA) or Millipore Sigma (St. Louis, MO, USA). Capsaicin (Cap) was purchased from Toronto Research Chemicals (North York, ON, CAN) and Δ 9 -tetrahydrocannabinol (THC) was purchased from Cerilliant (Round Rock, TX, USA). Anandamide (AEA) was purchased from Cayman Chemical (Ann Arbor, MI, USA).
Abdollahi M., Salem J.B., Castaño J.D., & Beaudry F. (2024). Anandamide Modulates Thermal Avoidance in Caenorhabditis elegans through Vanilloid and Cannabinoid Receptor Interplay.
Publication 2024
3
Mass Spectrometry Analysis of Endocannabinoid Secretion
Not available on PMC !

Example 6

The identification of AMEND was further narrowed down by mass spectrometry. Enriched AMEND preparation prepared from epithelial cells treated with or without verapamil were subjected to reversed-phase HPLC, revealing a specific peak in the absence of verapamil that contained potential AMEND compounds (FIG. 2D). Enriched AMEND preparations from control and P-gp deficient mice were subjected to electrospray mass spectrometry run in the positive ion mode (LC/MS), and it was found that levels of several endocannabinoids of both NAE and MAG classes were decreased in the absence of P-gp (Table 2). Qualitative analysis of relative abundance revealed a striking difference in peak profiles for H+ and Na+ adduct masses consistent with anandamide (AEA) (FIG. 2E). In order to determine which of these P-gp transported ECs exhibited actual AMEND inhibitory activity, purified compounds were tested in the cell-free migration assay. Only AEA, oleoyl ethanolamide (OEA), and alpha-linolenoyl ethanolamide (α-LEA) exhibited significant inhibitory activity, identifying these NAEs as putative AMEND components (FIG. 2F).

TABLE 2
Endocannabinoids are secreted from epithelial cells via P-gp.
Average*Std Error% of Control
Anandamidecontrol3.340.56
(AEA)B4-mdr1a1.960.0659
B5-mdr1a2.040.1361
Palmitoylcontrol27.205.14
ethanolamideB4-mdr1a10.871.5040
(PEA)B5-mdr1a2.200.268
Oleoylcontrol5.970.98
ethanolamideB4-mdr1a2.530.1242
(OEA)B5-mdr1a2.570.2143
2-Arachidonoylcontrol35.536.35
GlycerolB4-mdr1a32.171.3791
(2-AG)B5-mdr1a29.471.1983
Noladin ethercontrol33.4313.32
B4-mdr1a154.033.47461
B5-mdr1a56.231.32168
N-Arachidonoylcontrol0.000.00
DopamineB4-mdr1a1.970.06N/A
B5-mdr1a1.900.00N/A
*(normalized to anandamide-d8 standard, which was at 1 μg/μL)

With respect to Table 2, semi-quantitative MS analysis was performed to compare enriched AMEND preparations from control T84 cells to those with shRNA-mediated P-gp knockdown (B4-mdr1a and B5-mdr1a). Relative abundance of each compound was calculated by comparison with measured intensity of anandamide-d8 standard; while this is only accurately quantitative for anandamide itself, it allowed for comparison of relative units between samples for the remaining compounds.

US11865093B2. Methods and compositions for treating inflammation (2024-01-09). UNIVERSITY OF MASSACHUSETTS [US], UNIVERSITY OF BATH [GB]. Inventors: Randall Mrsny [US], Beth McCormick [US], Roland Ellwood Dolle [US].
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Patent 2024
4
Quantification of Endocannabinoids in Plasma
Not available on PMC !
The procedures for blood collection and analyses are explained in online Supplementary Methods S2. Briefly, venous blood samples were collected into ethylenediaminetetraacetic acid (EDTA) tubes. Given the fluctuations of plasma anandamide and 2-AG levels throughout the day (Hanlon, 2020; (link)Hanlon et al., 2016) (link), we strived to collect all blood samples in the late afternoon. Samples were centrifuged at room temperature. After centrifugation, 1.10 ml of plasma was stored in a -80 °C freezer in the presence of 1.10 μl of a 100 mM phenylmethanesulfonyl fluoride (PMSF) solution. PMSF is a serine protease inhibitor and prevents anandamide breakdown by fatty acid amide hydrolase (FAAH), which could potentially be released by blood cells during the venipuncture. Plasma concentrations (ng/ml) of anandamide and 2-AG were determined using previously published methods that are based on liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS) (Balvers, Verhoeckx, & Witkamp, 2009; (link)Balvers, Wortelboer, Witkamp, & Verhoeckx, 2013) (link). As 2-AG is prone to isomerization to 1-arachidonoylglycerol (1-AG) and as this is unavoidable in plasma, we reported the total concentration of plasma 1-AG plus 2-AG (hereafter labelled as 2-AG).
van Hooijdonk C.F.M., Balvers M.G.J., van der Pluijm M., Smith C.L.C., de Haan L., Schrantee A., Yaqub M., Witkamp R.F., van de Giessen E., van Amelsvoort T.A.M.J., Booij J, & Selten J.P. (2024). Endocannabinoid levels in plasma and neurotransmitters in the brain: a preliminary report on patients with a psychotic disorder and healthy individuals. Psychological medicine.
Publication 2024
5
Structural Prediction and Docking of TRPV1
Structural prediction of transmembrane protein topology (TMHMM, Transmembrane prediction using Hidden Markov Models) was performed from protein FASTA sequences using the platform provided by the Department of Health Technology at the Technical University of Denmark,4 which was made publicly available in 2001 (Krogh et al., 2001 (link)). Homology models were created using Phyre2 (Kelley and Sternberg, 2009 (link); Kelley et al., 2015 (link)). For docking of anandamide into TRPV1, the Cryo-EM structure of human TRPV1 in complex with the analgesic drug SB-366791 (PDB: 8GFA) was used. The A chain of the multimer was used with ligand and phospholipids removed from the .pdb file. The anandamide ligand (CHEMBL15848) was retrieved from the ChEMBL webserver as a .csv file and converted to a .pdb file using the Online SMILES Translator and Structure File Generator and then to a .pdbqt file with merged non-polar hydrogens with AutoDockTools version 1.5.7. The ligand was docked into the receptor using AutoDock Vina 1.1.2 (Trott and Olson, 2010 (link)) with a docking grid 20 Å in length in the x, y, and z directions centered on the “tunnel” anandamide-binding pocket previously identified (Morales et al., 2022 (link)), flexible N438, Y555, Y554, Y487 and D708 side-chains and an exhaustiveness of 20. Structural analysis was performed by superposition in PyMol (Schrödinger and DeLano, 2020 ). A professional academic license was acquired for PyMol.
Cherry A.L., Wheeler M.J., Mathisova K, & Di Miceli M. (2024). In silico analyses of the involvement of GPR55, CB1R and TRPV1: response to THC, contribution to temporal lobe epilepsy, structural modeling and updated evolution. Frontiers in Neuroinformatics, 18, 1294939.
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Publication 2024

Top products related to «Anandamide»

1
Anandamide by Merck Group
Sourced in United States, Germany
Anandamide is a naturally occurring endocannabinoid compound found in the human body. It plays a role in the endocannabinoid system and acts on cannabinoid receptors. Anandamide is used in laboratory research settings to study the effects of endocannabinoids.
2
Anandamide by Cayman Chemical
Sourced in United States
Anandamide is a naturally occurring endocannabinoid compound found in the human body. It serves as a neurotransmitter and plays a role in various physiological processes.
3
Bovine serum albumin (bsa) by Merck Group
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Bovine serum albumin (BSA) is a common laboratory reagent derived from bovine blood plasma. It is a protein that serves as a stabilizer and blocking agent in various biochemical and immunological applications. BSA is widely used to maintain the activity and solubility of enzymes, proteins, and other biomolecules in experimental settings.
4
Am251 by Bio-Techne
Sourced in United Kingdom, United States, Italy, France
AM251 is a synthetic cannabinoid receptor antagonist. It functions by selectively binding to and inhibiting the CB1 cannabinoid receptor.
5
High capacity cdna reverse transcription kit by Thermo Fisher Scientific
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The High-Capacity cDNA Reverse Transcription Kit is a laboratory tool used to convert RNA into complementary DNA (cDNA) molecules. It provides a reliable and efficient method for performing reverse transcription, a fundamental step in various molecular biology applications.
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Am630 by Bio-Techne
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AM630 is a high-performance liquid chromatography (HPLC) system designed for analytical and preparative chromatography applications. It offers precise flow control, high-pressure capabilities, and reliable performance for a wide range of sample types and separation methods.
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Urb597 by Cayman Chemical
Sourced in United States
URB597 is a selective and potent inhibitor of fatty acid amide hydrolase (FAAH), an enzyme responsible for the breakdown of the endocannabinoid anandamide. This compound is used in research applications to study the effects of FAAH inhibition and the role of the endocannabinoid system.
8
Dimethyl sulfoxide (dmso) by Merck Group
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DMSO is a versatile organic solvent commonly used in laboratory settings. It has a high boiling point, low viscosity, and the ability to dissolve a wide range of polar and non-polar compounds. DMSO's core function is as a solvent, allowing for the effective dissolution and handling of various chemical substances during research and experimentation.
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Fetal bovine serum (fbs) by Thermo Fisher Scientific
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Fetal Bovine Serum (FBS) is a cell culture supplement derived from the blood of bovine fetuses. FBS provides a source of proteins, growth factors, and other components that support the growth and maintenance of various cell types in in vitro cell culture applications.
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Lsrfortessa flow cytometer by BD
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The LSRFortessa flow cytometer is a high-performance instrument designed for cell analysis and sorting. It utilizes laser excitation and detectors to provide quantitative measurements of multiple parameters on individual cells within a sample. The core function of the LSRFortessa is to enable researchers and clinicians to analyze and sort a variety of cell types, including but not limited to, immune cells, stem cells, and tumor cells.

More about "Anandamide"

Anandamide, also known as N-arachidonylethanolamine (AEA), is a naturally occurring endogenous cannabinoid neurotransmitter found in the mammalian brain and other tissues.
It binds to and activates the same receptors as delta-9-tetrahydrocannabinol (THC), the psychoactive component in cannabis.
Anandamide plays a crucial role in pain perception, emotion, and memory, and has been implicated in a variety of physiological and pathological processes.
Researchers use various tools and techniques to study anandamide, including bovine serum albumin (BSA) as a carrier protein, the antagonists AM251 and AM630, the fatty acid amide hydrolase (FAAH) inhibitor URB597, and dimethyl sulfoxide (DMSO) as a solvent.
The High-Capacity cDNA Reverse Transcription Kit is often used to analyze gene expression related to anandamide signaling.
Flow cytometry techniques, such as the LSRFortessa flow cytometer, can be employed to assess the effects of anandamide on cellular processes.
PubCompare.ai, an innovative AI-driven platform, helps researchers optimize their anandamide studies by identifying the most accurate and reproducible protocols from scientific literature, preprints, and patents.
This enhances research efficiency and reliability, allowing scientists to make more informed decisions and progress their investigations into the fascinating world of this endocannabinoid neurotransmitter.