2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor
Abstract
Two types of endogenous cannabinoid-receptor agonists have been identified thus far. They are the ethanolamides of polyunsaturated fatty acids—arachidonoyl ethanolamide (anandamide) is the best known compound in the amide series—and 2-arachidonoyl glycerol, the only known endocannabinoid in the ester series. We report now an example of a third, ether-type endocannabinoid, 2-arachidonyl glyceryl ether (noladin ether), isolated from porcine brain. The structure of noladin ether was determined by mass spectrometry and nuclear magnetic resonance spectroscopy and was confirmed by comparison with a synthetic sample. It binds to the CB1 cannabinoid receptor (Ki = 21.2 ± 0.5 nM) and causes sedation, hypothermia, intestinal immobility, and mild antinociception in mice. It binds weakly to the CB2 receptor (Ki > 3 μM).
- Publication:
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Proceedings of the National Academy of Science
- Pub Date:
- March 2001
- DOI:
- 10.1073/pnas.061029898
- Bibcode:
- 2001PNAS...98.3662H
- Keywords:
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- Chemistry