R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE

R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE
  • CAS No.:157182-49-5
Other grades of this product :
R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE 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:157182-49-5
MF:C23H39NO2
MW:361.56
EINECS:200-578-6
Product Categories:Cannabinoid receptor;Cannabinoid
Mol File:157182-49-5.mol
R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE Chemical Properties
Boiling point 529.0±50.0 °C(Predicted)
density 0.935±0.06 g/cm3(Predicted)
RTECS JX3848000
Fp 14℃
storage temp. −20°C
pka14.51±0.10(Predicted)
form Colorless oil.
optical activity[α]/D +8.7°, c = 4 in chloroform(lit.)
Sensitive Air & Light Sensitive
Safety Information
Hazard Codes F
Risk Statements 11
Safety Statements 7-16
RIDADR UN 1170 3/PG 2
WGK Germany 1
MSDS Information
ProviderLanguage
SigmaAldrich English
R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE Usage And Synthesis
DescriptionR-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).
UsesMethanandamide is a metabolically stable endocannabinoid analogue of the mammalian brain ligand Anandamide. Methanandamide is known to improve myocardial resistance against arrhythmogenic effects and can also be used to modulate behaviors caused by Amphetamine (HCl: A634248).
Biological ActivityStable 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 ActionsR(+)-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.
R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE Preparation Products And Raw materials

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