R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE
Synonym(s):AM-356;R(+)-Arachidonyl-1′-hydroxy-2′-propylamide
- CAS NO.:157182-49-5
- Empirical Formula: C23H39NO2
- Molecular Weight: 361.56
- MDL number: MFCD00467914
- EINECS: 200-578-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-06-08 09:03:07
What is R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE?
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).
The Uses of R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE
Methanandamide 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).
What are the applications of Application
(R)-Methanandamide is a potent CB1 agonist and VR agonist
Definition
ChEBI: Methanandamide is a fatty amide.
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.
Properties of R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE
Boiling point: | 529.0±50.0 °C(Predicted) |
Density | 0.935±0.06 g/cm3(Predicted) |
RTECS | JX3848000 |
Flash point: | 14℃ |
storage temp. | −20°C |
solubility | DMF: >10 mg/ml; DMSO: >30 mg/ml; Ethanol: >100 mg/ml; Ethanol:PBS (1:2): 8.5 mg/ml; PBS (pH 7.2): <100 μg/ml |
pka | 14.51±0.10(Predicted) |
form | Colorless oil. |
optical activity | [α]/D +8.7°, c = 4 in chloroform(lit.) |
Sensitive | Air & Light Sensitive |
Safety information for R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE
Signal word | Danger |
Pictogram(s) |
Flame Flammables GHS02 Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H225:Flammable liquids H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P337+P313:IF eye irritation persists: Get medical advice/attention. P405:Store locked up. P403+P235:Store in a well-ventilated place. Keep cool. |
Computed Descriptors for R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE
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