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A0580

Arachidonylethanolamide

Name: Arachidonylethanolamide
Brand: SIGMA

≥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

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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)

Related Categories

Biochemicals

Coenzymes

Proteins & Enzymes

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)

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Certificates of Analysis (COA)

Lot/Batch Number

0000548564

0000519382

0000513930

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Hypothalamic endocannabinoids inversely correlate with the development of diet-induced obesity in male and female mice.

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

Simulation of Swanson's literature-based discovery: anandamide treatment inhibits growth of gastric cancer cells in vitro and in silico.

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

Dynamic changes to the endocannabinoid system in models of chronic pain.

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

Cellular and intracellular mechanisms involved in the cognitive impairment of cannabinoids.

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

Arachidonyl ethanolamide induces apoptosis of uterine cervix cancer cells via aberrantly expressed vanilloid receptor-1.

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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Global Trade Item Number

SKU	GTIN
A0580-25MG	04061833334126
A0580-5MG	04061833334133

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