Anandamide (Synonyms: AEA, Anandamide) |
Catalog No.GC35339
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Anandamide, an endocannabinoid derived from arachidonic acid-containing membrane lipids, exerts its actions by binding and activating CB1 and CB2 receptors (cannabinoid receptors 1 and 2) and the vanilloid transient receptor potential vanilloid 1 (TRPV1) receptor.
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Cas No.: 94421-68-8
Sample solution is provided at 25 µL, 10mM.
Anandamide, an endocannabinoid derived from arachidonic acid-containing membrane lipids, exerts its actions by binding and activating CB1 and CB2 receptors (cannabinoid receptors 1 and 2) and the vanilloid transient receptor potential vanilloid 1 (TRPV1) receptor[1-2]. Anandamide is involved in the regulation of pain, mood, and cognition[3].
In vitro, primary microglial cultures were pretreated with 1μM Anandamide for 30min, stimulated with 100ng/mL Lipopolysaccharide (LPS) for 24h, and assayed for nitric oxide; LPS alone markedly increased nitric oxide (NO) release, whereas Anandamide reduced it by ~30%[4]. Pretreating human vascular smooth muscle cells (hVSMC) with 100nM Anandamide for 1h (protein assays) or 2.5h (immunofluorescence and PLA) suppressed the cytokine-induced expression of 21 inflammatory genes, including the key chemokine CCL2, by elevating H3K27me3 and reducing H3K27ac at the CCL2 promoter, thereby compacting chromatin[5].
In vivo, after intraperitoneal administration of Anandamide (10mg/kg) to mice, hyperglycemia after oral glucose loading was improved, whereas glucose clearance and insulin sensitivity were impaired, without altering transporter-mediated glucose absorption[6]. Following two bilateral intracerebroventricular injections (2μL; 1μL/min; 100ng) of Anandamide to male Wistar rats, Anandamide prevented streptozotocin (STZ)-induced deficits in recognition and non-associative emotional memory without affecting tone fear conditioning, blocked STZ-elicited enlargement of the cerebral ventricles, and, like STZ, decreased Bcl2-associated athanogene (BAG2) levels[7].
References:
[1] Goodfellow CE, Glass M. Anandamide receptor signal transduction. Vitam Horm. 2009;81:79-110.
[2] Biringer RG. The rise and fall of anandamide: processes that control synthesis, degradation, and storage. Mol Cell Biochem. 2021;476(7):2753-2775.
[3] Leweke FM, Piomelli D, Pahlisch F, et al. Cannabidiol enhances anandamide signaling and alleviates psychotic symptoms of schizophrenia. Transl Psychiatry. 2012;2(3):e94. Published 2012 Mar 20.
[4] Malek N, Popiolek-Barczyk K, Mika J, et al. Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures. Neural Plast. 2015;2015:130639.
[5] Pflüger-Müller B, Oo JA, Heering J, et al. The endocannabinoid anandamide has an anti-inflammatory effect on CCL2 expression in vascular smooth muscle cells. Basic Res Cardiol. 2020;115(3):34.
[6] Troy-Fioramonti S, Demizieux L, Gresti J, et al. Acute activation of cannabinoid receptors by anandamide reduces gastrointestinal motility and improves postprandial glycemia in mice. Diabetes. 2015;64(3):808-818.
[7] Moreira-Silva D, Carrettiero DC, Oliveira ASA, et al. Anandamide Effects in a Streptozotocin-Induced Alzheimer's Disease-Like Sporadic Dementia in Rats. Front Neurosci. 2018;12:653.
| Cell experiment [1]: | |
Cell lines | Primary microglial cell |
Preparation Method | Adherent cells were incubated for 48h in culture medium before being used for the analyses. Primary microglial cell cultures were treated with 1μM Anandamide for 30min and then for 24h with Lipopolysaccharide (LPS) (100ng/mL) for mRNA analysis. |
Reaction Conditions | 1μM; 30min |
Applications | An increase in the secretion of nitric oxide (NO) was observed 24h after the administration of LPS (100ng/mL). Anandamide (1μM) administered 30min prior to LPS stimulation reduced NO production by approximately 30%. |
| Animal experiment [2]: | |
Animal models | Male Wistar rats |
Preparation Method | Each animal received two intracerebroventricular (icv) bilateral injections of 2μL (1μL/min): the first one was citrate (vehicle) or Anandamide (100ng), followed by another injection of vehicle or streptozotocin (STZ) (2mg/kg) 5min later. After each infusion, the injection needle remained for at least 2min in place, to prevent reflux of the administered solution. After surgery, animals received intramuscular injections of an antibiotic and an anti-inflammatory, and an analgesic. Also, 2mL of saline solution was administered subcutaneously for rehydration, and the animals were maintained in thermal blankets with controlled temperature until recovery. Animals were kept in individual home cages for 5 days after surgery, and body weight, food, water intake, and animal well-being were accompanied daily. |
Dosage form | 2μL; 1μL/min; 100ng; intracerebroventricular (icv) bilateral injections |
Applications | Anandamide prevented recognition and non-associative emotional memory impairments induced by STZ, but did not influence tone fear conditioning. STZ increased the brain ventricular area, and this enlargement was prevented by Anandamide. Bcl2-associated athanogene (BAG2) levels were decreased by STZ and Anandamide. |
References: | |
| Cas No. | 94421-68-8 | SDF | |
| Synonyms | AEA, Anandamide | ||
| Chemical Name | N-(2-hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide | ||
| Canonical SMILES | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(NCCO)=O | ||
| Formula | C22H37NO2 | M.Wt | 347.53 |
| Solubility | 30mg/mL in DMSO, or 10mg/mL in DMF | Storage | Store at -20°C,stored under nitrogen |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.8774 mL | 14.3872 mL | 28.7745 mL |
| 5 mM | 575.5 μL | 2.8774 mL | 5.7549 mL |
| 10 mM | 287.7 μL | 1.4387 mL | 2.8774 mL |
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Quality Control & SDS
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- Purity: >98.00% Appearance: An oil
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Average Rating: 5 (Based on Reviews and 21 reference(s) in Google Scholar.)