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O-Arachidonoyl Ethanolamine (hydrochloride)

Cayman Chemical Item Number 91050

Virodhamine; O-AEA; Arachidonic Acid-(2-aminoethyl)-ester (CAS 443129-35-9)

O-Arachidonoyl Ethanolamine (hydrochloride) (CAS 443129-35-9)

See more	Endocannabinoids (54) Neuroscience (654)

Description

Arachidonoyl ethanolamide (AEA) was the first endogenous cannabinoid to be isolated and characterized as an agonist acting on the same receptors (CB₁ and CB₂) as tetrahydrocannabinols (THC).^1,2 Since that time, a number of related endocannabinoids have been isolated, most notably 2-arachidonoyl glycerol (2-AG).³ 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.^1,2,4 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.⁵

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 Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB₁ receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J Biochem 122 890-895 (1997).

4 Porter, A.C., Sauer, J., 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).

5 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. J Biol Chem 274 2794-2801 (1999).

Synonyms	Virodhamine O-AEA Arachidonic Acid-(2-aminoethyl)-ester
Formal Name	O-(2-aminoethyl)-5Z,8Z,11Z,14Z-eicosatetraenester, monohydrochloride
CAS Number	443129-35-9
Molecular Formula	C₂₂H₃₇NO₂ · HCl
Formula Weight	384.0
Formulation	A neat oil
Purity	>98%
Stability	6 months
Storage	-80°C
Shipping	Dry ice in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard CCCCC\C=C/C\C=C/C/C=C\C/C=C\CCCC(OCCN)=O.Cl

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).

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).

Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB₁ receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J Biochem 122 890-895 (1997).

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. J Biol Chem 274 2794-2801 (1999).

Porter, A.C., Sauer, J., 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).

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O-Arachidonoyl Ethanolamine (hydrochloride) is available in the following screening library:

Bio-active Lipid I Screening Library (96-Well)

Size	Price	Quantity	Subtotal
1 mg	$35.00		$0.00
5 mg	$158.00		$0.00
10 mg	$280.00		$0.00
25 mg	$613.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-02-12. Prices are subject to change without notice.

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