157182-49-5

Basic information

• Product Name: R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE
• Synonyms: AM 356;(R)-METHANANDAMIDE;R(+)-METHANANDAMIDE;(R)-N-(2-HYDROXY-1-METHYLETHYL)-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE;N-(2-HYDROXY-1R-METHYLETHYL)-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE;N-(2R-HYDROXYPROPYL)-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE;R-1 METHANANDAMIDE;R-2 METHANANDAMIDE
• CAS NO: 157182-49-5
• Molecular Formula: C₂₃H₃₉NO₂
• Molecular Weight: 361.56
• EINECS: 200-578-6
• Product Categories: Cannabinoid receptor;Cannabinoid
• Mol File: 157182-49-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 529 °C at 760 mmHg
• Flash Point: 14℃
• Appearance: Colorless oil
• Density: 0.935 g/cm³
• Vapor Pressure: 2.11E-13mmHg at 25°C
• Refractive Index: 1.501
• Storage Temp.: −20°C
• PKA: 14.51±0.10(Predicted)
• Sensitive: Air & Light Sensitive
• CAS DataBase Reference: R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE(157182-49-5)
• EPA Substance Registry System: R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE(157182-49-5)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16
• RIDADR: UN 1170 3/PG 2
• WGK Germany: 1
• RTECS: JX3848000
• Hazardous Substances Data: 157182-49-5(Hazardous Substances Data)

Usage

Description

R-1 methanandamide is a potent cannabinoid (CB) receptor 1 agonist in the methanandamide series. It is selective for CB1 over CB2 receptors with Ki values ranging from 17.9 to 28.3 and 815 to 868 nM, respectively. R-1 methanandamide is more potent than arachidonoyl ethanolamide (AEA; ). In addition, R-1 methanandamide is more resistant than AEA to hydrolytic inactivation by fatty acid amide hydrolase (FAAH).

Biological Activity

Stable anandamide analog that is a selective agonist for the CB 1 receptor (K i values are 20 and 815 nM for CB 1 and CB 2 receptors respectively). Also displays agonist activity at vanilloid receptors. Also available in water-soluble emulsion ((R)-N-(2-Hydroxy-1-methylethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide ) and as part of the Cannabinoid CB 1 Receptor Tocriset? .

Biochem/physiol Actions

R(+)-Methanandamide is metabolically stable congener of anandamide that has higher affinity for the cannabinoid receptor. Of the analogs tested, (R)-methanandamide exhibited the highest affinity for the cannabinoid receptor with a Ki of 20 +/- 1.6 nM, 4-fold lower than that of anandamide (Ki = 78 +/- 2 nM). (R)-methanandamide exhibits high stability to aminopeptidase hydrolysis. Experiments with mice have demonstrated that (R)-methanandamide also posseses cannabimimetric properties in vivo, as established by the four tests of hypothermia, hypokinesia, ring immobility, and antinociception.

InChI:InChI=1/C23H39NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(26)24-22(2)21-25/h7-8,10-11,13-14,16-17,22,25H,3-6,9,12,15,18-21H2,1-2H3,(H,24,26)/b8-7-,11-10-,14-13-,17-16-/t22-/m1/s1

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 35320-23-1 (R)-2-aminopropan-1-ol 
• 57303-04-5 arachidonoyl chloride 

Downstream Products

• 1313514-76-9 (+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (4-benzoyl-L-phenylalaninate) 
• 1313514-83-8 (+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} 4-benzoyl-N-(5-hexynoyl)-L-phenylalaninate 
• 1313514-75-8 (+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (2S)-3-(4-benzoylphenyl)-2-[(tert-butoxycarbonyl)amino]propanoate 

Relevant articles and documents

Anandamide prodrugs: 1. Water-soluble phosphate esters of arachidonylethanolamide and R-methanandamide

Phosphate esters of arachidonylethanolamide (AEA) and R-methanandamide were synthesized and evaluated as water-soluble prodrugs. Various physicochemical properties (pKa, partition coefficient, aqueous solubility) were determined for the synthesized phosphate esters. The chemical stability of phosphate esters was determined at pH 7.4. In vitro enzymatic hydrolysis rates were determined in 10% liver homogenate, and in a pure enzyme-containing (alkaline phosphatase) solution at pH 7.4. The intraocular pressure (IOP) lowering properties of R-methanandamide phosphate ester were tested on normotensive rabbits. The phosphate promoiety increased the aqueous solubility of the parent compounds by more than 16 500-fold at pH 7.4. Phosphate esters were stable in buffer solutions, but rapidly hydrolyzed to their parent compounds in alkaline phosphatase solution (t1/21/2=8-9 min). The phosphate ester of R-methanandamide reduced IOP in rabbits. These results indicate that the phosphate esters of AEA and R-methanandamide are useful water-soluble prodrugs.