157182-50-8

Basic information

• Product Name: S-1 METHANANDAMIDE
• Synonyms: N-(2-HYDROXY-1S-METHYLETHYL)-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE;S-1 METHANANDAMIDE;S(-)-METHANANDAMIDE;(S)-(-)-ARACHIDONOYL-1'-HYDROXY-2'-PROPYLAMIDE;S(-)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE;S-1 Methanandamide Exclusive;(5Z,8Z,11Z,14Z)-N-[(2S)-1-hydroxypropan-2-yl]icosa-5,8,11,14-tetraenamide
• CAS NO: 157182-50-8
• Molecular Formula: C23H39NO2
• Molecular Weight: 361.56
• Mol File: 157182-50-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 529.0±50.0 °C(Predicted)
• Appearance: /
• Density: 0.935±0.06 g/cm3(Predicted)
• Solubility: Soluble in DMSO;dimethyl formamide;acetonitril
• PKA: 14.51±0.10(Predicted)
• CAS DataBase Reference: S-1 METHANANDAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: S-1 METHANANDAMIDE(157182-50-8)
• EPA Substance Registry System: S-1 METHANANDAMIDE(157182-50-8)

Safety Data

• Hazardous Substances Data: 157182-50-8(Hazardous Substances Data)

Usage

Biological Activity

s-1 methanandamide is a cb1 receptor ligand.the cannabinoid receptor type 1 (cb1), is a g protein-coupled cannabinoid receptor located mainly in the central and peripheral nervous system. cb1 is also expressed in several cells relating to metabolism, such as muscle cells, fat cells, liver cells, and the digestive tract. the cb1 receptor has been involved in the maintenance of homeostasis in health and disease, preventing the development of excessive neuronal activity, reducing pain and other inflammatory symptoms. enhanced receptor expression has been identified in human hepatocellular carcinoma tumor samples and human prostate cancer cells [2].s-1 methanandamide was a less potent than the c-1 (r) methyl isomer when binding with cb1 receptor. s-1 methanandamide inhibited electrically evoked contractions in isolated mouse vasa deferentia with an ic50 value of 230 nm. the binding affinity of s-1 methanandamide for cb1 receptors was less than that of aea, with a ki of 175 nm for the displacement of radiolabeled cp 55,940 [1].

Upstream product

• 35320-23-1 (R)-2-aminopropan-1-ol 
• 69287-38-3 5,8,11,14-eicosatetraenoic acid methyl ester 
• 6168-72-5 2-Amino-1-propanol 
• 95285-77-1 ethyl arachidonate 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 57303-04-5 arachidonoyl chloride 
• 2749-11-3 (S)-Alaninol 

Relevant articles and documents

Pharmacological and behavioral evaluation of alkylated anandamide analogs

Anandamide (arachidonylethanolamide), isolated from porcine brain, has been shown to bind to the cannabinoid receptor and also to produce cannabimimetic activity in pharmacological assays. This study examined structure-activity relationships in alkylated anandamide analogs. The analogs were evaluated for their ability to displace [3H]CP-55,940 in a filtration binding assay using rat brain membranes in the presence and absence of the enzyme inhibitor phenylmethylsulfonyl fluoride (PMSF). Behavioral activity was assessed by the ability of the analogs to produce hypomotility and antinociception. Methylations at carbons 2 and 1' produced compounds stable in the absence of PMSF with similar affinities and behavioral activity as anandamide. Addition of larger alkyl groups at these positions or nitrogen methylation reduced receptor affinity and behavioral potency. These results indicate that methylations at specific carbons of anandamide confer stability in vitro.

Enzymatic synthesis of N-acylethanolamines: Direct method for the aminolysis of esters

Immobilized Candida antarctica (Novozyme 435) catalyzed synthesis of N-acylethanolamines is described. Treatment of methyl esters with lipase and amines yielded the desired amides within 2-24 h with yields ranging from 41% to 98%.

(R)-methanandamide: A chiral novel anandamide possessing higher potency and metabolic stability

Four chiral congeners of arachidonylethanolamide (anandamide) have been synthesized and evaluated for (a) their ability to bind to the cannabinoid receptor in rat forebrain membranes and (b) their pharmacological potency as measured by the compounds' ability to inhibit electrically-evoked contractions of the mouse vas deferens. The lead analog was also tested for its potency in vivo. Of the analogs tested, (R)-(+)-arachidonyl-1'-hydroxy- 2'-propylamide [(R)-methanandamide] exhibited the highest affinity for the cannabinoid receptor with a K(i) of 20 ± 1.6 nM, 4-fold lower than that of anandamide (K(i) = 78 ± 2 nM). Moreover, determination of the cannabinoid binding affinity in the presence and absence of the protease inhibitor phenylmethanesulfonyl fluoride (PMSF) revealed that (R)-methanandamide possesses a remarkable stability to aminopeptidase hydrolysis. Pharmacological studies on mouse isolated vasa deferentia demonstrated that all four analogs produce concentration-related inhibition of the twitch response and the order of potency is the same as the rank order of the affinities of these agonists for cannabinoid binding sites. Furthermore, experiments with mice have demonstrated that (R)-methanandamide also possesses cannabimimetric properties in vivo, as established by the four tests of hypothermia, hypokinesia, ring immobility, and antinociception.