An internal standard for the quantification of linoleoyl ethanolamide
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Unlabeled Version(s)
90155Linoleoyl Ethanolamide
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Linoleoyl Ethanolamide-d4

Item No. 9000553

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl-1,1,2,2-d4)-9Z,12Z-octadecadienamide
CAS Number
1451194-69-6
Synonyms
  • LEA-d4
Molecular Formula
C20H33D4NO2
Formula Weight
327.5
Purity
≥99% deuterated forms (d1-d4)
Formulation
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlEthanol: 50 mg/mlEthanol:PBS (pH 7.2)(1:2): 100 µg/ml
SMILES
O=C(NC([2H])([2H])C([2H])([2H])O)CCCCCCC\C=C/C/C=C\CCCCC
InChi Code
InChI=1S/C20H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h6-7,9-10,22H,2-5,8,11-19H2,1H3,(H,21,23)/b7-6-,10-9-/i18D2,19D2
InChi Key
KQXDGUVSAAQARU-UKNLGWMGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $36

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    1 mg

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    5 mg

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    Product Description

    Linoleoyl ethanolamide-d4 contains four deuterium atoms at the hydroxyethyl 1,1',2, and 2' positions. It is intended for use as an internal standard for the quantification of linoleoyl ethanolamide (Item No. 90155) by GC- or LC-mass spectrometry. 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 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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(27), 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. 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).