10004281  R-1 Methanandamide Phosphate

R-1MAP; (R)-(+)-Arachidonyl-1'-Hydroxy-2'-Propylamide Phosphate



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• See more Cannabinoids; Fatty Acid Amides; Neuroscience

For active pharmaceutical ingredients (APIs) related to R-1 Methanandamide Phosphate, see Cayman Pharma

Arachidonoyl ethanolamide (AEA) was the first endogenous cannabinoid (CB) to be isolated and characterized as an agonist acting on the same receptors (CB1 and CB2) as Δ9-THC.1,2 Since that time, a number of related endocannabinoids have been isolated, most notably 2-arachidonoyl glycerol (2-AG).2 The phosphate ester of R-1 methanandamide, R-1MAP, has been tested as a water soluble prodrug analog of AEA.3 The activity of R-1MAP was essentially equivalent to that of AEA in the growth inhibition of C6 glioma cells. However, when tested for inhibition of AEA binding to isolated rat brain CB1 receptors, arachidonoyl ethanolamide phosphate (AEA-P) is about 5-fold less potent as an agonist with a Ki of about 200 nM.4 The phosphate esters of AEA and its analogs are also structural variants of lysophosphatidic acid (LPA). However, the effects of R-1MAP on the various LPA receptors have not been tested.
1  Devane, W.A., Hanus, L., Breuer, A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258 1946-1949 (1992).
2  Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci USA 90 7656-7660 (1993).
3  Fowler, C.J., Jonsson, K., Andersson, A., et al. Inhibition of C6 glioma cell proliferation by anandamide, 1-arachidonoylglycerol, and by a water soluble phosphate ester of anandamide: Variability in response and involement of arachidonic acid. Biochem Pharmacol 66 757-767 (2003).
4  Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J Med Chem 40 659-667 (1997).

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Pricing Information

Prices listed here are the Manufacturer's Suggested European Retail Price. The actual prices quoted by each individual distributor may vary. Please visit the Global Buyer's Guide on the Cayman Chemical (world) website to locate a distributor in your region.

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Size Price Quantity
1 mg €84.00
5 mg €378.00
10 mg €672.00
50 mg €2,940.00
Pricing updated 2010-09-07.
Prices are subject to change without notice.