GLPBio

Anandamide

Catalog No.: GC35339Purity:>98.00%Synonyms: AEA, Anandamide
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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Anandamide
Cas No.: 94421-68-8
10mM (in 1mL DMSO)In Stock
$62.00
1
1mgIn Stock
$21.00
1
5mgIn Stock
$56.00
1
10mgIn Stock
$109.00
1
25mgIn Stock
$210.00
1

Citations

1 publicationsPublications from researchers using this product

Description

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.

Protocol

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:
[1] 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.
[2] 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.

Product Documents

Purity:>98.00%Appearance:An oil

Biological Data

1 / 1

Chemical Properties

CAS No.
94421-68-8
Synonyms
AEA, Anandamide
Chemical Name
N-(2-hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(NCCO)=O
Molecular Formula
C22H37NO2
Molecular Weight
347.53
Solubility
30mg/mL in DMSO, or 10mg/mL in DMF
Storage
Store at -20°C,stored under nitrogen
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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