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.
A0580
Arachidonylethanolamide
≥97.0% (TLC), oil
Synonym(e):
Anandamide (20:4, n-6), AEA, Anandamide, Arachidonic acid N-(hydroxyethyl)amide
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5 MG
€ 120,00
25 MG
€ 318,00
Über diesen Artikel
Empirische Formel (Hill-System):
C22H37NO2
CAS-Nummer:
Molekulargewicht:
347.53
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
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Unterstützung erhaltenInChI
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-
SMILES string
O=C(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)NCCO
InChI key
LGEQQWMQCRIYKG-DOFZRALJSA-N
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
Quality Level
Gene Information
rat ... Cnr1(25248)
Verwandte Kategorien
1 of 4
Dieser Artikel | |||
|---|---|---|---|
| assay ≥97.0% (TLC) | assay ≥99% (TLC and GC) | assay ~98% (TLC) | assay >99% (TLC) |
| form oil | form oil | form powder | form liquid |
| shipped in dry ice | shipped in dry ice | shipped in - | shipped in dry ice |
| solubility ethanol: soluble | solubility ethanol: 5 mg/mL | solubility chloroform: 20 mg/mL, clear, colorless | solubility - |
| storage temp. −20°C | storage temp. −70°C | storage temp. −20°C | storage temp. −70°C |
| density 0.92 g/mL at 25 °C (lit.) | density - | density - | density - |
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.
Disclaimer
Protect from light and moisture.
Lagerklasse
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Emma Puighermanal et al.
Philosophical transactions of the Royal Society of London. Series B, Biological sciences, 367(1607), 3254-3263 (2012-10-31)
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
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
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
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
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
Verwandter Inhalt
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Can solutions of Product A0580, Arachidonylethanolamide, be stored?
1 answer-
Helpful?
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What is the Department of Transportation shipping information for this product?
1 answer-
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.
Helpful?
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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).
Helpful?
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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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