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A0580
Arachidonylethanolamide
≥97.0% (TLC), oil
Synonym(s):
Anandamide (20:4, n-6), AEA, Anandamide, Arachidonic acid N-(hydroxyethyl)amide
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All Photos(2)
About This Item
Empirical Formula (Hill Notation):
C22H37NO2
CAS Number:
Molecular Weight:
347.53
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25
Pricing and availability is not currently available.
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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.)
lipid type
omega FAs
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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Application
- Interactions Between Endocannabinoid and Endogenous Opioid Systems Prospectively Influence Postoperative Opioid Use in Pregnant Patients Undergoing Cesarean Delivery: Investigates Arachidonylethanolamide′s interactions with opioid systems, providing insights that could lead to better management of postoperative pain and opioid use (Stone et al., 2024).
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
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Devi Rani Sagar et al.
Philosophical transactions of the Royal Society of London. Series B, Biological sciences, 367(1607), 3300-3311 (2012-10-31)
The analgesic effects of cannabinoid ligands, mediated by CB1 receptors are well established. However, the side-effect profile of CB1 receptor ligands has necessitated the search for alternative cannabinoid-based approaches to analgesia. Herein, we review the current literature describing the impact
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Exogenous cannabinoids, such as delta9-tetrahydrocannabinol (THC), as well as the modulation of endogenous cannabinoids, affect cognitive function through the activation of cannabinoid receptors. Indeed, these compounds modulate a number of signalling pathways critically implicated in the deleterious effect of cannabinoids
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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
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
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What is the Department of Transportation shipping information for this product?
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How to dissolve Product A0580, Arachidonylethanolamide?
1 answer-
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).
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Is Product A0580, Arachidonylethanolamide, a solution?
1 answer-
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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Can solutions of Product A0580, Arachidonylethanolamide, be stored?
1 answer-
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.
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