222723-55-9

Basic information

• Product Name: NOLADIN ETHER
• Synonyms: 2-[(5Z,8Z,11Z,14Z)-EICOSATETRAENYLOXY]-1,3-PROPANEDIOL;2-AG ETHER;2-ARACHIDONYL GLYCERYL ETHER;2-ARACHIDONYL GLYCEROL ETHER;5Z,8Z,11Z,14Z-EICOSATETRAEN-2-GLYCERYL ETHER;NOLADIN ETHER;Noladineether;2-[(5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraen-1-yloxy]-1,3-propanediol
• CAS NO: 222723-55-9
• Molecular Formula: C23H40O3
• Molecular Weight: 364.56
• EINECS: 200-578-6
• Product Categories: Cannabinoid receptor
• Mol File: 222723-55-9.mol

Chemical Properties

• Boiling Point: 488.9 °C at 760 mmHg
• Flash Point: 14℃
• Appearance: colorless to light yellow/
• Density: 0.948 g/cm³
• Vapor Pressure: 1.31E-11mmHg at 25°C
• Refractive Index: 1.502
• Storage Temp.: Desiccate at -20°C
• CAS DataBase Reference: NOLADIN ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: NOLADIN ETHER(222723-55-9)
• EPA Substance Registry System: NOLADIN ETHER(222723-55-9)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16
• RIDADR: UN1170 - class 3 - PG 2 - Ethanol, solution
• WGK Germany: 2
• Hazardous Substances Data: 222723-55-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
NOLADIN ETHER is used as a research compound for investigating the biological roles of GPR55 and CB1 receptors. This application helps in understanding the functions and potential therapeutic applications of these receptors in various conditions.
Used in Ophthalmology:
In the field of ophthalmology, NOLADIN ETHER is used as a potential treatment for reducing intraocular pressure in rabbits. It achieves this by increasing aqueous humor outflow via the CB1 receptor in the trabecular meshwork, which can be beneficial in managing glaucoma.
Used in Nutritional Research:
NOLADIN ETHER is used as a research tool to study its effects on dietary intake and fat consumption in rats. It has been shown to increase dietary intake and enhance fat consumption when administered to the nucleus accumbens, which can provide insights into the role of CB1 receptors in appetite regulation and obesity research.
Used in Drug Development:
NOLADIN ETHER can be used as a starting point for the development of new drugs targeting CB1 and GPR55 receptors. Its chemical stability and agonistic properties make it a promising candidate for the development of therapeutics for various conditions, including pain management, inflammation, and neurological disorders.

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? .

InChI:InChI=1/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-

Upstream product

• 500910-43-0 2-(5,8,11,14-eiosatetraenyl)-1,3-benzylideneglycerol 
• 13487-46-2 arachidonyl alcohol 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 331253-80-6 5,8,11,14-eicosatetraenyl iodide 

Relevant articles and documents

COMPOSITIONS HAVING AN AGENT AND AN ENHANCER THEREOF, METHODS OF USE, AND DELIVERY SYSTEMS

The present invention relates to compositions, and methods of use thereof, related to the endocannabinoid system and includes therapeutic compositions including an agent and an enhancer thereof, optionally, formulated for administration of the therapeutic compositions, preferably in a measured amount.

Synthetic endogenous cannabinoids analogues and uses thereof

The present invention relates to a compound of the general formula (I) which is a non-hydrolysable analogue of endogenous cannabinoids, which are found to be more potent therapeutic agents as they are more stable, for example, to hydrolytic cleavage in the gastrointestinal tract. The cannabinoid analogues of the invention have a therapeutic value. Therefore, pharmaceutical compositions comprising as active ingredient a therapeutically effective amount of at least one compound of the invention may be prepared. Such compositions may be used as anti-inflammatory, anti-asthmatic, analgetic, hypotensive, antiemetic or anti-spasmodic compositions, and as compositions for treating and/or preventing glaucoma or migraine, or as compositions for relieving symptoms of multiple sclerosis and mood stimulating compositions.

Synthesis and biological activities of 2- arachidonoylglycerol, an endogenous cannabinoid receptor ligand, and its metabolically stable ether-linked analogues

We synthesized 2-arachidonoylglycerol (1), an endogenous cannabinoid receptor ligand, and its metabolically stable ether- linked analogues. Compound 1 was synthesized from 1,3- benzylideneglycerol (6) and arachidonic acid in the presence of N,N'-dicyclohexylcarbodiimide and 4-dimethylaminopyridine followed by treatment with boric acid and trimethyl borate. An ether-linked analogue of 2-arachidonoylglycerol (2) was synthesized from 6 and 5,8,11,14-eicosatetraenyl iodide (9). The ether-linked analogues of 2-palmitoylglycerol (4) and 2- oleoyglycerol (5) were synthesized from 6 and hexadecyl iodide (12) and 9-octadecenyl iodide (14), respectively. We confirmed that 1 stimulates NG108-15 cells to induce rapid transient elevation of the intracellular free Ca2+ concentrations through a CB1 receptor-dependent mechanism. Noticeably, 2 exhibited appreciable agonistic activity, although its activity was significantly lower than that of 1. Compound 2 would be a useful tool in exploring the physiological significance of 1, because this compound is resistant to hydrolyzing enzymes in contrast to 1. On the other hand, the ether-linked analogues of either 4 or 5 failed to act as a CB1 receptor agonist. Compounds 4 and 5 would also be valuable as control molecules in experiments where 2 is employed.