2-Arachidonyl Glycerol ether (CAS 222723-55-9) | Cayman Chemical
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2-Arachidonyl Glycerol ether

Item № 62165
CAS № 222723-55-9
Purity ≥98%
product image
                (CAS 222723-55-9)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $20.00 0.00
     5 mg $90.00 0.00
     10 mg $160.00 0.00
     25 mg $350.00 0.00

Pricing updated 2018-10-20. Prices are subject to change without notice.

Description
Synonyms
  • 2-AG ether
  • Noladin

2-Arachidonyl glycerol ether (2-AG ether) selectively binds to cannabinoid (CB) receptor 1 (Kis = 21.2 and >3,000 nM for CB1 and CB2, respectively, in a radioligand binding assay).1 It is a potent and selective agonist of CB1 and GPR55 with EC50 values of 10, 37, and >30,000 nM for CB1, GPR55, and CB2, respectively.2 2-AG ether displays the typical tetrad of CB activities in mice.1 It is more chemically stable than 2-AG (Item No. 62160), with an endogenous half-life of hours rather than minutes.3 However, it is at least 10-fold less potent than 2-AG in eliciting typical CB1-mediated responses.4 2-AG ether elicits modest reductions in intraocular pressure in rabbits when administered at doses exceeding 50 µg per eye.3 It increases aqueous humor outflow via the CB1 receptor in the trabecular meshwork.5 Administration of 2-AG ether to the nucleus accumbens (0.0625-1 μg) increases dietary intake and enhances fat consumption in rats given access to both high-carbohydrate and high-fat diets.6

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Technical Information
Formal Name
5Z,8Z,11Z,14Z-eicosatetraen-2-glyceryl ether
CAS Number
222723-55-9
Synonyms
  • 2-AG ether
  • Noladin
Molecular Formula
C23H40O3
Formula Weight
364.6
Purity
≥98%
Formulation
A solution in ethanol
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCOC(CO)CO
InChI Code
InChI=1S/C23H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26-23(21-24)22-25/h6-7,9-10,12-13,15-16,23-25H,2-5,8,11,14,17-22H2,1H3/b7-6-,10-9-,13-12-,16-15-
InChI Key
CUJUUWXZAQHCNC-DOFZRALJSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
Stability
≥ 6 months
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Additional Information

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References & Product Citations
Product Description References

1. Hanus, L., Abu-Lafi, S., Fride, E., et al. 2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor. Proc. Nat. Acad. Sci. USA 98(7), 3662-3665 (2001).

2. Ryberg, E., Larsson, N., Sjögren, S., et al. The orphan receptor GPR55 is a novel cannabinoid receptor. British Journal of Pharmacology 152, 1092-1101 (2007).

3. Laine, K., Jarvinen, K., Mechoulam, R., et al. Comparison of the enzymatic stability and intraocular pressure effects of 2-arachidonylglycerol and noladin ether, a novel putative endocannabinoid. Investigative Ophthalmology & Visual Science 43(10), 3216-3222 (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. J. Biol. Chem. 274(5), 2794-2801 (1999).

5. Njie, Y.F., Kumar, A., Qiao, Z., et al. Noladin ether acts on trabecular meshwork cannabinoid (CB1) receptors to enhance aqueous humor outflow facility. Investigative Ophthalmology & Visual Science 47(5), 1999-2005 (2006).

6. Deshmukh, R.R., and Sharma, P.L. Stimulation of accumbens shell cannabinoid CB1 receptors by noladin ether, a putative endocannabinoid, modulates food intake and dietary selection in rats. Pharmacol. Res. 66(3), 276-282 (2012).

Product Citations

Caires, R., Sierra-Valdez, F.J., Millet, J.R.M., et al. Omega-3 fatty acids modulate TRPV4 function through plasma membrane remodeling. Cell Reports 21, 245-258 (2017).

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