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Merck
CN

A0580

Sigma-Aldrich

花生四烯酸乙醇胺

≥97.0% (TLC), oil

别名:

苯酰胺 (20:4, n-6), AEA, 大麻素, 花生四烯酸 N-(羟乙基)酰胺

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About This Item

经验公式(希尔记法):
C22H37NO2
CAS号:
分子量:
347.53
MDL编号:
UNSPSC代码:
12352211
PubChem化学物质编号:
NACRES:
NA.25

质量水平

检测方案

≥97.0% (TLC)

形式

oil

药品控制

regulated under CDSA - not available from Sigma-Aldrich Canada

颜色

colorless to light yellow

溶解性

ethanol: soluble

密度

0.92 g/mL at 25 °C (lit.)

脂质类型

omega FAs

运输

dry ice

储存温度

−20°C

SMILES字符串

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

基因信息

rat ... Cnr1(25248)

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应用


  • 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).

生化/生理作用

一种花生四烯酸衍生物,是 CB 大麻素受体和 VR1 香草素受体的内源性配体。抑制神经母细胞瘤和神经元中的钙电流。激活 MAP 激酶信号通路。抑制淋巴细胞和人类乳腺癌细胞的增殖并诱导细胞凋亡。

注意

避光避潮保存。

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)


分析证书(COA)

输入产品批号来搜索 分析证书(COA) 。批号可以在产品标签上"批“ (Lot或Batch)字后找到。

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    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. 

  5. How to dissolve Product A0580, Arachidonylethanolamide?

    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).

  6. Can solutions of Product A0580, Arachidonylethanolamide, be stored?

    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.   

  7. Is Product A0580, Arachidonylethanolamide, a solution?

    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).

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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
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
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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