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Cat. Number

653089805027580

Chemical Name

Linoleoyl Ethanolamide-d4

References

Formal Name	N-(2-hydroxyethyl-1,1,2,2-d4)-9Z,12Z-octadecadienamide
Molecular Formula	C₂₀H₃₃D₄NO₂
Formula Weight	327.5
Formulation	A solution in ethanol
Purity	≥99% deuterated product
Stability	1 year
Storage	-20°C
Shipping	Wet ice in continental US; may vary elsewhere
SMILES	O=C(NC([2H])([2H])C([2H])([2H])O)CCCCCCCC=C/C/C=CCCCCC

Background Reading

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).

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).

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).

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).

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).

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).

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).

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Size	Global Purchasing
100 µg
500 µg
1 mg
5 mg

Description

Linoleoyl ethanolamide is an endocannabinoid detected in porcine brain and murine peritoneal macrophages which contains linoleate in place of the arachidonate moiety of arachidonoyl ethanolamide (AEA).^1,2 It has weak affinity for the central cannabinoid (CB₁) and peripheral cannabinoid (CB₂) receptors, exhibiting K_i 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 K_i 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).

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