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

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

form 

Colorless oil.

pka

14.51±0.10(Predicted)

optical activity

[α]/D +8.7°, c = 4 in chloroform(lit.)

Sensitive 

Air & Light Sensitive

Safety

Hazard Codes 

F

Risk Statements 

11

Safety Statements 

7-16

RIDADR 

UN 1170 3/PG 2

WGK Germany 

1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE Chemical Properties,Usage,Production

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 K_i 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).

Uses

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).

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.