NOLADIN ETHER Chemical Properties

Boiling point:

488.9±45.0 °C(Predicted)

Density 

0.948±0.06 g/cm3(Predicted)

Flash point:

14℃

storage temp. 

Desiccate at -20°C

solubility 

DMF: 20 mg/ml; DMSO: 15 mg/ml; Ethanol: 25 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 500 μg/ml

pka

13.92±0.10(Predicted)

form 

ethanol solution (10 mg/mL (1% w/v))

color 

colorless to light yellow

Safety Information

Hazard Codes 

F

Risk Statements 

11

Safety Statements 

7-16

RIDADR 

UN1170 - class 3 - PG 2 - Ethanol, solution

WGK Germany 

2

NOLADIN ETHER Usage And Synthesis

Description

2-Arachidonyl glycerol ether (2-AG ether) selectively binds to cannabinoid (CB) receptor 1 (K_is = 21.2 and >3,000 nM for CB₁ and CB₂, respectively, in a radioligand binding assay). 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-AG ether displays the typical tetrad of CB activities in mice. It is more chemically stable than 2-AG , with an endogenous half-life of hours rather than minutes. However, it is at least 10-fold less potent than 2-AG in eliciting typical CB₁-mediated responses. 2-AG ether elicits modest reductions in intraocular pressure in rabbits when administered at doses exceeding 50 μg per eye. It increases aqueous humor outflow via the CB₁ receptor in the trabecular meshwork. 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.

Uses

HU 310 is an endogenous GPR55 and CB1 receptors agonist. HU 310 has been shown to induce hyperglycia in rats. HU 310 can be used to investigate the biological roles of GPR55 and CB1 receptors.

Definition

ChEBI: A monoalkylglycerol that is the 2-O-arachidonyl derivative of glycerol.

Biological Activity

Endogenous agonist for the GPR55 and CB 1 receptors (EC 50 values are 10 and 37 nM respectively) that displays selectivity over CB 2 receptors (K i values are 21.2 nM and > 3mM at CB 1 and CB 2 respectively). Causes sedation, hypothermia, intestinal immobility and mild antinociception in vivo . Attenuates sensory neurotransmission in rat mesenteric arteries via GPR55. Also available as part of the Endocannabinoid Tocriset™ .

IC 50

CB1: 21.2 nM (Ki); CB2: >3 mM (Ki)

References

[1] L. HANU?. 2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor[J]. Proceedings of the National Academy of Sciences of the United States of America, 2001, 98 1: 3662-3665. DOI: 10.1073/pnas.061029898
[2] E RYBERG. The orphan receptor GPR55 is a novel cannabinoid receptor[J]. British Journal of Pharmacology, 2009, 152 7: 1092-1101. DOI: 10.1038/sj.bjp.0707460
[3] KRISTA LAINE. Comparison of the enzymatic stability and intraocular pressure effects of 2-arachidonylglycerol and noladin ether, a novel putative endocannabinoid.[J]. Investigative ophthalmology & visual science, 2002, 43 10: 3216-3222.
[4] T SUGIURA. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds.[J]. The Journal of Biological Chemistry, 1999, 274 5: 2794-2801. DOI: 10.1074/jbc.274.5.2794
[5] YA FATOU NJIE. Noladin ether acts on trabecular meshwork cannabinoid (CB1) receptors to enhance aqueous humor outflow facility.[J]. Investigative ophthalmology & visual science, 2006, 47 5: 1999-2005. DOI: 10.1167/iovs.05-0729
[6] RAHUL R. DESHMUKH  P. L S. Stimulation of accumbens shell cannabinoid CB1 receptors by noladin ether, a putative endocannabinoid, modulates food intake and dietary selection in rats[J]. Pharmacological research, 2012, 66 3: Pages 276-282. DOI: 10.1016/j.phrs.2012.06.004

NOLADIN ETHER(222723-55-9)Related Product Information

• 1-OCTADECANOYL-2-[(CIS,CIS,CIS,CIS)-5,8,11,14-EICOSATETRAENOYL]-SN-GLYCERO-3-PHOSPHOCHOLINE
• 1,2-DI5,8,11,14(ALL-CIS)EICOSATETRAENOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
• 2-AG-D5
• 1-STEAROYL-2-ARACHIDONOYL-SN-GLYCEROL
• 2-AG
• 1-O-HEXADECYL-2-ARACHIDONYL-SN-GLYCERO-3-PHOSPHOCHOLINE
• 2-AG-D8
• NOLADIN ETHER
• 1-STEAROYL-2-ARACHIDONOYL-PHOSPHATIDYLINOSITOL 3,4,5-TRIPHOSPHATE, (NA+ SALT)
• TRIARACHIDONIN
• PHOSPHATIDYLCHOLINE, L-ALPHA-1-STEAROYL-2-ARACHIDONYL, [ARACHIDONYL-5,6,8,9,11,12,14,15-3H(N)]
• 2-ARACHIDONYL GLYCEROL [ARACHIDONYL 5,6,8,9,11,12,14,15-3H(N)]
• 3-STERAOYL-2-ARACHIDONYL-SN-GLYCEROL
• PHOSPHATIDYLCHOLINE, L-ALPHA-1-PALMITOYL-, 2-ARACHIDONYL, [ARACHIDONYL-1-14C]
• PHOSPHATIDYLCHOLINE, L-ALPHA-1-O HEXADECYL-1-2-ARACHIDONYL, [ARACHIDONYL-5,6,8,9,11,12,14,15-3H(N)]
• PHOSPHATIDYLETHANOLAMINE, L-ALPHA-1-PALMITOYL, 2-ARACHIDONYL, [ARACHIDONYL-1-14C]
• 1-STEAROYL-2-[1-14C]ARACHIDONYL-SN-GLYCEROL
• L-3-PHOSPHATIDYLCHOLINE,1-STEAROYL-2-[1-14C]ARACHIDONYL