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

15(S)-HETE Ethanolamide

Cayman Chemical Item Number 10169

15(S)-HAEA (CAS 161744-53-2)

15(S)-HETE Ethanolamide (CAS 161744-53-2)

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Description

Arachidonoyl ethanolamide (AEA) was the first endogenous cannabinoid (CB) to be isolated and characterized as an agonist acting on the same receptors (CB1 and CB2) as THC.1,2 Since that time, a number of related endocannabinoids have been isolated, most notably 2-arachidonoyl glycerol.2 Lipoxygenases, especially rabbit reticulocyte and soybean 15-lipoxygenases, actively convert endocannabinoids to their 15(S)-hydroperoxy and hydroxy metabolites.3 15(S)-HETE ethanolamide is less potent than AEA at the CB1 receptor (Ki of 600 versus 90 nM). 15(S)-HETE ethanolamide also inhibits fatty acid amide hydrolase.4

1 Devane, W.A., Hanus, L., Breuer, A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258 1946-1949 (1992).

2 Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci USA 90 7656-7660 (1993).

3 Ueda, N., Yamamoto, K., Kurahashi, Y., et al. Oxygenation of arachidonylethanolamide (anandamide) by lipoxygenases. Adv Prostaglandin Thromboxane Leukot Res 23 163-165 (1995).

4 van der Stelt, M., van Kuik, A., Bari, M., et al. Oxygenated metabolites of anandamide and 2-arachidonoylgycerol: Conformational analysis and interaction with cannabinoid receptors, membrane transporter, and fatty acid amide hydrolase. J Med Chem 45 3709-3720 (2002).

Synonyms
  • 15(S)-HAEA
Formal Name 15(S)-​hydroxy-​N-​(2-​hydroxyethyl)-​5Z,​8Z,​11Z,​13E-​eicosatetraenamide
CAS Number 161744-53-2
Molecular Formula C22H37NO3
Formula Weight 363.5
Formulation A solution in ethanol
Purity ≥98%
λmax 236 nm
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O[C@@H]​(CCCCC)​/C=C/C=C\C/C=C\C/C=C\CCCC(NCCO)​=O

Background Reading

Devane, W.A., Hanus, L., Breuer, A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258 1946-1949 (1992).

van der Stelt, M., van Kuik, A., Bari, M., et al. Oxygenated metabolites of anandamide and 2-arachidonoylgycerol: Conformational analysis and interaction with cannabinoid receptors, membrane transporter, and fatty acid amide hydrolase. J Med Chem 45 3709-3720 (2002).

Ueda, N., Yamamoto, K., Kurahashi, Y., et al. Oxygenation of arachidonylethanolamide (anandamide) by lipoxygenases. Adv Prostaglandin Thromboxane Leukot Res 23 163-165 (1995).

Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci USA 90 7656-7660 (1993).

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15(S)-HETE Ethanolamide is available in the following screening library:

Size Price Quantity Subtotal
25 µg $120.00 $0.00
50 µg $228.00 $0.00
100 µg $432.00 $0.00
500 µg $1,920.00 $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 2012-02-12. 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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Show all 6 Hide all but first 3

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