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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

Linoleoyl Ethanolamide

Cayman Chemical Item Number 90155

(CAS 68171-52-8)

Linoleoyl Ethanolamide (CAS 68171-52-8)

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Description

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

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. Chem Phys 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. J Med Chem 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. Biol Pharm Bull 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. Biochem J 360 67-75 (2001).

6 Maccarrone, M., van der Stelt, M., Rossi, A., et al. Anandamide hydrolysis by human cells in culture and brain. J Biol Chem 273 32332-32339 (1998).

7 Bisogno, T., Maurelli, S., Melck, D., et al. Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes. J Biol Chem 272 3315-3323 (1997).

Formal Name N-​(2-​hydroxyethyl)-​9Z,​12Z-​octadecadienamide
CAS Number 68171-52-8
Molecular Formula C20H37NO2
Formula Weight 323.5
Formulation A solution in ethanol
Purity >98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C/C=C\CCCCCCCC(=O)​NCCO

Background Reading

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).

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. Biol Pharm Bull 22(4) 366-370 (1999).

Berdyshev, E.V., Schmid, P.C., Krebsbach, R.J., et al. Cannabinoid-receptor-independent cell signalling by N-acylethanolamines. Biochem J 360 67-75 (2001).

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. J Med Chem 41 5353-5361 (1998).

Schmid, P.C., Kuwae, T., Krebsbach, R.J., et al. Anandanide and other N-acylethanolamines in mouse peritoneal macrophages. Chem Phys Lipids 87 103-110 (1997).

Maccarrone, M., van der Stelt, M., Rossi, A., et al. Anandamide hydrolysis by human cells in culture and brain. J Biol Chem 273 32332-32339 (1998).

Bisogno, T., Maurelli, S., Melck, D., et al. Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes. J Biol Chem 272 3315-3323 (1997).

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Linoleoyl Ethanolamide is available in the following screening library:

Size Price Quantity Subtotal
5 mg $34.00 $0.00
10 mg $65.00 $0.00
50 mg $272.00 $0.00
100 mg $476.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-11. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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