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A0580

Sigma-Aldrich

Arachidonylethanolamide

≥97.0% (TLC), oil

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C22H37NO2
Numéro CAS:
94421-68-8
Poids moléculaire :
347.53
Numéro MDL:
MFCD00153766
Code UNSPSC :
12352211
ID de substance PubChem :
24890438
Nomenclature NACRES :
NA.25

Niveau de qualité

200

Pureté

≥97.0% (TLC)

Forme

oil

Contrôle du médicament

regulated under CDSA - not available from Sigma-Aldrich Canada

Couleur

colorless to light yellow

Solubilité

ethanol: soluble

Densité

0.92 g/mL at 25 °C (lit.)

Type de lipide

omega FAs

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

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-

Clé InChI

LGEQQWMQCRIYKG-DOFZRALJSA-N

Informations sur le gène

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).

Actions biochimiques/physiologiques

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.

Attention

Protect from light and moisture.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Sigma-Aldrich

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Sigma-Aldrich

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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
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
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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