A natural, mixed agonist/antagonist of the CB1 receptor
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O-Arachidonoyl Ethanolamine (hydrochloride)

Item No. 91050

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5Z,8Z,11Z,14Z-eicosatetraenoic acid, 2-aminoethyl ester, monohydrochloride
CAS Number
443129-35-9
Synonyms
  • O-AEA
  • Arachidonic Acid-(2-aminoethyl)-ester
  • Virodhamine
Molecular Formula
C22H37NO2 • HCl
Formula Weight
384.0
Purity
≥98%
Formulation
A neat oil
Solubility(Learn about Variance in Solubility)
DMF: 40 mg/mlDMSO: 40 mg/mlEthanol: 20 mg/mlPBS: > 100 µg/ml
SMILES
CCCCC\C=C/C\C=C/C/C=C\C/C=C\CCCC(OCCN)=O.Cl
InChi Code
InChI=1S/C22H37NO2.ClH/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23;/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3;1H/b7-6-,10-9-,13-12-,16-15-;
InChi Key
BNTZVCDZOZGRSZ-XVSDJDOKSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    1 mg

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    10 mg

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    25 mg

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    Product Description

    O-Arachidonoyl ethanolamine hydrochloride (O-AEA) is a recently isolated constituent of human and rat brain wherein the ethanolamine moiety is attached “backwards”, as an ester instead of an amide, as in AEA.1,2,3 O-AEA has mixed agonist/antagonist activity at the CB1 receptor and does not appear to be the native endogenous cannabinoid agonist at this receptor. This is in keeping with other observations that 2-AG is the primary endogenous CB1 receptor ligand.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. Porter, A.C., Sauer, J.M., Knierman, M.D., et al. Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor. J. Pharmacol. Exp. Ther. 301(3), 1020-1024 (2002).

    4. Sugiura, T., Kodaka, T., Nakane, S., et al. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. The Journal of Biological Chemisty 274(5), 2794-2801 (1999).

    Product Citations

    Kantae, V., Ogino, S., Noga, M., et al. Quantitative profiling of endocannabinoids and related N-acylethanolamines in human CSF using nano LC-MS/MS. J. Lipid. Res. 58(3), 615-624 (2017).