A CB1 receptor ligand and FAAH inhibitor
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15(S)-HETE Ethanolamide

Item No. 10169

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
15(S)-hydroxy-N-(2-hydroxyethyl)-5Z,8Z,11Z,13E-eicosatetraenamide
CAS Number
161744-53-2
Synonyms
  • 15(S)-HAEA
  • 15(S)-Hydroxyeicosatetraenoic Acid Ethanolamide
Molecular Formula
C22H37NO3
Formula Weight
363.5
Purity
≥98%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 50 mg/mlEthanol:PBS (pH 7.2) (1:2): 5 mg/mlPBS (pH 7.2): 0.10 mg/ml
λmax
236 nm
SMILES
O[C@@H](CCCCC)/C=C/C=C\C/C=C\C/C=C\CCCC(NCCO)=O
InChi Code
InChI=1S/C22H37NO3/c1-2-3-13-16-21(25)17-14-11-9-7-5-4-6-8-10-12-15-18-22(26)23-19-20-24/h4-5,8-11,14,17,21,24-25H,2-3,6-7,12-13,15-16,18-20H2,1H3,(H,23,26)/b5-4-,10-8-,11-9-,17-14+/t21-/m0/s1
InChi Key
XZQKRCUYLKDPEK-BPVVGZHASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $169

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    50 µg

    $319

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    100 µg

    $602

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    Product Description

    Arachidonoyl ethanolamide (AEA; Item No. 90050) 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 (Item No. 62160).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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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(5090), 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(16), 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).