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S-1 Methanandamide (Synonyms: (S)-(−)-Arachidonyl-1'-Hydroxy-2'-Propylamide)

Catalog No.GC13605

CB1 receptor ligand

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S-1 Methanandamide Chemical Structure

Cas No.: 157182-50-8

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5mg
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25mg
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

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].

References:
[1] Abadji V, Lin S, Taha G, et al.  (R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability[J]. Journal of medicinal chemistry, 1994, 37(12): 1889-1893.
[2] Howlett A C.  Cannabinoid receptor signaling[M]//Cannabinoids. Springer Berlin Heidelberg, 2005: 53-79.

Chemical Properties

Cas No. 157182-50-8 SDF
Synonyms (S)-(−)-Arachidonyl-1'-Hydroxy-2'-Propylamide
Chemical Name N-(2-hydroxy-1S-methylethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Canonical SMILES CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(N([C@@H](C)CO)[H])=O
Formula C23H39NO2 M.Wt 361.6
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 µ g/ml Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 2.7655 mL 13.8274 mL 27.6549 mL
5 mM 0.5531 mL 2.7655 mL 5.531 mL
10 mM 0.2765 mL 1.3827 mL 2.7655 mL
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