Linoleoyl Ethanolamide

An endocannabinoid

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库存: 现货

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2mg

￥575.00

460.00

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5mg

￥812.00

650.00

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10mg

￥1212.00

970.00

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25mg

￥2212.00

1770.00

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50mg

￥3325.00

2660.00

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货号: ajci72386
CAS: 68171-52-8
别名: 亚油醇乙醇胺,LEA
分子式: C20H37NO2
分子量: 323.5
纯度: >98%
溶解度: 25 mg/ml in DMSO, 25 mg/ml in DMF, 50 mg/ml in Ethanol
储存: Store at -20°C
库存: 现货

Background

Linoleoyl ethanolamide is an endocannabinoid detected in porcine brain and murine peritoneal macrophages which contains linoleate in place of the arachidonate moiety of arachidonyl ethanolamide (AEA). [1] [2] It has weak affinity for the cannabinoid 1 (CB1) and CB2 receptors, exhibiting Ki values of 10 µM and 25 µM, respectively.[3]? However, it is only approximately 4-fold less potent than AEA at causing catalepsy in mice (ED50 of 26.5 mg/kg). [4] In addition, linoleoyl ethanolamide increases ERK phosphorylation and AP-1-dependent transcription approximately 1.5 fold at 15 µM in a CB-receptor-independent manner.[5]? However, cellular toxicity is readily apparent at concentrations of 10-20 µM. Linoleoyl ethanolamide inhibits human fatty acid amide hydrolase-dependent hydrolysis of AEA with a Ki value of 9.0 µM, but also is hydrolyzed effectively by the enzyme. [6][7]?

Reference:
[1]. Patrono, C., Rotella, C.M., Toccafondi, R.S., et al. Prostacyclin stimulates the adenylate cyclase system of human thyroid tissue. Prostaglandins 22(1), 105-115 (1981).
[2]. Schmid, P.C., Kuwae, T., Krebsbach, R.J., et al. Anandanide and other N-acylethanolamines in mouse peritoneal macrophages. Chemistry and Physics of Lipids 87, 103-110 (1997).
[3]. Lin, S., Khanolkar, A.D., Fan, P., et al. Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability. Journal of Medicinal Chemistry 41, 5353-5361 (1998).
[4]. Watanabe, K., Matsunaga, T., Nakamura, S., et al. Pharmacological effects in mice of anandamide and its related fatty acid ethanolamides, and enhancement of cataleptogenic effect of anandamide by phenylmethylsulfonyl fluoride. Biological and Pharmaceutical Bullentin 22(4), 366-370 (1999).
[5]. Berdyshev, E.V., Schmid, P.C., Krebsbach, R.J., et al. Cannabinoid-receptor-independent cell signalling by N-acylethanolamines. Biochemistry Journal 360, 67-75 (2001).
[6]. Maccarrone, M., van der Stelt, M., Rossi, A., et al. Anandamide hydrolysis by human cells in culture and brain. The Journal of Biological Chemisty 273, 32332-32339 (1998).
[7]. Bisogno, T., Maurelli, S., Melck, D., et al. Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes. The Journal of Biological Chemisty 272, 3315-3323 (1997).