A0580

Sigma-Aldrich

Arachidonylethanolamide

≥97.0% (TLC), oil

Synonym(s):
Anandamide, AEA, Anandamide (20:4, n-6), Arachidonic acid N-(hydroxyethyl)amide
Empirical Formula (Hill Notation):
C22H37NO2
CAS Number:
Molecular Weight:
347.53
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

≥97.0% (TLC)

form

oil

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

color

colorless to light yellow

solubility

ethanol: soluble

density

0.92 g/mL at 25 °C (lit.)

shipped in

dry ice

storage temp.

−20°C

SMILES string

O=C(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)NCCO

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-

InChI key

LGEQQWMQCRIYKG-DOFZRALJSA-N

Gene Information

rat ... Cnr1(25248)

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Related Categories

Packaging

5, 25 mg in ampule

Biochem/physiol Actions

An arachidonic acid derivative that is an endogenous ligand for the CB cannabinoid receptor and for the VR1 vanilloid receptor. Inhibits calcium currents in neuroblastomas and neurons. Activates the MAP kinase signaling pathway. Inhibits proliferation and induces apoptosis of lymphocytes and human breast cancer cells.

Caution

Protect from light and moisture.

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. How to dissolve Product A0580, Arachidonylethanolamide?

    Arachidonylethanolamide (also known as anandamide) is soluble in ethanol (100 mM) and in DMSO (10 mg/ml) and is poorly soluble in water.  Hydroxypropyl -β cyclodextran has been reported to increase the aqueous solubility and stability of anandamide. Jarho, P. et al., Life Sciences, 58, 181 (1996).

  6. Can solutions of Product A0580, Arachidonylethanolamide, be stored?

    Sigma has not evaluated the solution stability of this product.  Solutions in ethanol, stored under argon at -20°C, have been reported (see Schuel, H.. et al., Proc. Nat. Acad. Sci., USA, 91, 7678-7682 (1994) and Spivak, C.E., Mol. Pharmacol., 72, 1024-1032 (2007)).  If solutions are to be stored, it would be best to use a degassed solvent or solvent purged with argon. Store solutions under argon in the freezer, at -20°C or colder.  Store solutions protected from light and oxygen to prevent the oxidation of the double bonds.   

  7. Is Product A0580, Arachidonylethanolamide, a solution?

    No, the product is naturally an oily liquid. An approximate molarity for the liquid is 2.6 M (based on a molecular weight of 347.5 g/mole and an approximate density of 0.92 g/mL at 25°C).

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Bala Attili et al.
British journal of pharmacology, 176(10), 1481-1491 (2018-12-28)
Non-invasive in vivo imaging of cannabinoid CB2 receptors using PET is pursued to study neuroinflammation. The purpose of this study is to evaluate the in vivo binding specificity of [18 F]MA3, a CB2 receptor agonist, in a rat model with...
Emmanuel Contassot et al.
Gynecologic oncology, 93(1), 182-188 (2004-03-30)
Delta(9)-Tetrahydrocannabinol, the active agent of Cannabis sativa, exhibits well-documented antitumor properties, but little is known about the possible effects mediated by endogenous cannabinoids on human tumors. In the present study, we analyzed the effect of arachidonyl ethanolamide (AEA) on cervical...
Cristina Miralpeix et al.
Journal of lipid research, 60(7), 1260-1269 (2019-05-30)
The endocannabinoid (eCB) system regulates energy homeostasis and is linked to obesity development. However, the exact dynamic and regulation of eCBs in the hypothalamus during obesity progression remain incompletely described and understood. Our study examined the time course of responses...
Weiwei Dong et al.
PloS one, 9(6), e100436-e100436 (2014-06-21)
Swanson's literature-based discovery focus on resurrecting previously published but neglected knowledge. In this study, we propose a two-step model of the discovery process and generate a hypothesis between anandamide and gastric cancer. Further, the potential relationship was confirmed by follow-up...
Eline N Kuipers et al.
Frontiers in physiology, 9, 1913-1913 (2019-01-29)
The endocannabinoid system (ECS) controls energy balance by regulating both energy intake and energy expenditure. Endocannabinoid levels are elevated in obesity suggesting a potential causal relationship. This study aimed to elucidate the rate of dysregulation of the ECS, and the...

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