Anandamide

Alias: Arachidonylethanolamide; Anandamide; AEA; Arachidonoyl ethanolamide
Cat No.:V11283 Purity: ≥98%
Anandamide is an endocannabinoid.
Anandamide Chemical Structure CAS No.: 94421-68-8
Product category: Cannabinoid Receptor
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description
Anandamide is an endocannabinoid. Anandamide regulates neuronal and immune function through two protein-coupled cannabinoid receptors (CB1 and CB2). Anandamide activates multiple receptors like PPARS, TRPV1 and GPR18/GPR55. Anandamide also has anti-fungal and anti~inflammatory activities. Anandamide may be utilized in the research into Alzheimer's disease (AD) and ulcerative colitis.
Biological Activity I Assay Protocols (From Reference)
Targets
CB1; CB2; PPAR; TRPV1; Microbial Metabolite; Human Endogenous Metabolite
ln Vitro
Anandamide (0-250 μg/ml, 1 h) inhibits the growth of Candida albicans hyphae and stops them from adhering to epithelial cells[4].
Anandamide (0-250 μg/ml, 2 h) modifies the expression of genes related to hyphal morphogenesis and adhesion[4].
Anandamide inhibits the activity of protein kinases, which lowers tau phosphorylation[3].
ln Vivo
Anandamide (10 mg/kg, IP, once) improves glucose tolerance by significantly reducing the rise in glycemia in response to glucose ingestion when compared to control[2].
Anandamide (100 ng, ICV bilateral injection, single) partially mitigates the cognitive deficits, alterations in synaptic markers, and ventricle enlargement caused by streptozotocin (STZ)[3].
Anandamide reduces the development of inflammation by acting as an anti-inflammatory in a mouse model of ulcerative colitis[4].
Anandamide reduces lipopolysaccharide (LPS)-induced neuroinflammation in rat primary microglial cultures[1].
Cell Assay
Cell Line: HeLa cervical epithelial cells
Concentration: 0, 10, 50, 125, 250 μg/ml
Incubation Time: 2 h
Result: Repressed the expression of the HWP1 and ALS3 adhesins involved in Candida adhesion to epithelial cells and the HGC1, RAS1, EFG1 and ZAP1 regulators of hyphal morphogenesis and cell adherence. Increased the expression of NRG1, a transcriptional repressor of filamentous growth.
Animal Protocol
Male Wistar rats (3-4 months, 350-400 g, STZ-induced AD-like sporadic dementia model)
100 ng
ICV bilateral injection, single
References

[1]. Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures. Neural Plast. 2015;2015:130639.

[2]. Acute activation of cannabinoid receptors by Anandamide reduces gastrointestinal motility and improves postprandial glycemia in mice. Diabetes. 2015 Mar;64(3):808-18.

[3]. Anandamide Effects in a Streptozotocin-Induced Alzheimer's Disease-Like Sporadic Dementia in Rats. Front Neurosci. 2018 Sep 21;12:653.

[4]. Anandamide prevents the adhesion of filamentous Candida albicans to cervical epithelial cells. Sci Rep. 2020 Aug 13;10(1):13728.

[5]. The endocannabinoid anandamide has an anti-inflammatory effect on CCL2 expression in vascular smooth muscle cells. Basic Res Cardiol. 2020 Apr 22;115(3):34.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C22H37NO2
Molecular Weight
347.53468
Exact Mass
361.26
Elemental Analysis
C, 73.09; H, 9.76; N, 3.87; O, 13.28
CAS #
94421-68-8
Appearance
A solution in ethanol
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO
InChi Key
LGEQQWMQCRIYKG-DOFZRALJSA-N
InChi Code
InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-
Chemical Name
(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
Synonyms
Arachidonylethanolamide; Anandamide; AEA; Arachidonoyl ethanolamide
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ≥ 100 mg/mL (~287.7 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.99 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (5.99 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (5.99 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8774 mL 14.3872 mL 28.7745 mL
5 mM 0.5755 mL 2.8774 mL 5.7549 mL
10 mM 0.2877 mL 1.4387 mL 2.8774 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02727023 Completed Other: Osteopathic Manipulative
Medicine
Anandamide
Endocannabinoids
New York Institute of Technology December 2015 Not Applicable
Biological Data
  • Effect of anandamide on blood glucose clearance and insulin sensitivity. Diabetes . 2015 Mar;64(3):808-18.
  • Effect of anandamide on intestinal glucose transport. Diabetes . 2015 Mar;64(3):808-18.
  • Effect of anandamide on gastrointestinal motility and on glycemia after duodenal glucose loading. Diabetes . 2015 Mar;64(3):808-18.
  • Anandamide prevents yeast-hypha transition. Sci Rep . 2020 Aug 13;10(1):13728.
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