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Merck

A0580

Arachidonylethanolamide

≥97.0% (TLC), oil

Synonym(s):

Anandamide (20:4, n-6), AEA, Anandamide, Arachidonic acid N-(hydroxyethyl)amide

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About This Item

Empirical Formula (Hill Notation):
C22H37NO2
CAS Number:
94421-68-8
Molecular Weight:
347.53
NACRES:
NA.25
PubChem Substance ID:
24890438
UNSPSC Code:
12352211
MDL number:
MFCD00153766

Key Documents

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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-

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

200

Gene Information

rat ... Cnr1(25248)

Related Categories

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.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

A0580-VAR: + A0580-BULK: + A0580-5MG: + A0580PROC: + A0580-25MG: + A0580-5MG-PW: + A0580-PH:

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Certificates of Analysis (COA)

Lot/Batch Number
0000519382
0000519382
0000513930
0000513930
0000416165

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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
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
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
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