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A0580

Sigma-Aldrich

Arachidonylethanolamide

≥97.0% (TLC), oil

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C22H37NO2
Číslo CAS:
94421-68-8
Molekulová hmotnost:
347.53
MDL number:
MFCD00153766
UNSPSC Code:
12352211
PubChem Substance ID:
24890438
NACRES:
NA.25

Quality Level

200

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Osvědčení o analýze (COA)

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C17:0 anandamide phosphate Avanti Research™ - A Croda Brand 870437P, powder

Avanti

870437P

C17:0 anandamide phosphate

AEA-d4 C20:4 anandamide-d4, methanol solution

Avanti

857465W

AEA-d4

Palmitoylethanolamide

Sigma-Aldrich

P0359

Palmitoylethanolamide

Linoleyl ethanolamide ≥98%, ethanol solution

Sigma-Aldrich

L1164

Linoleyl ethanolamide

Stearoyl ethanolamide ≥98%, crystalline

Sigma-Aldrich

S8439

Stearoyl ethanolamide

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
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
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
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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