R-1 Methanandamide Phosphate (Synonyms: R-1MAP,(R)-(+)-Arachidonyl-1'-Hydroxy-2'-Propylamide Phosphate) |
| Catalog No.GC14177 |
CB1 receptor agonist
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 649569-33-5
Sample solution is provided at 25 µL, 10mM.
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R-1 Methanandamide Phosphate,a water soluble prodrug analog of AEA, exhibited similar activity to that of AEA in the growth inhibition of C6 glioma cells[1].
Arachidonoyl ethanolamide (AEA) was the first endogenous cannabinoid (CB). AEA has been isolated and characterized as an agonist acting on the receptors CB1 and CB2 [2,3]. Since then, several related endocannabinoids have been isolated, most notably was 2-arachidonoyl glycerol (2-AG). The phosphate ester of R-1 methanandamide, R-1MAP, has been tested as a water soluble prodrug analog of AEA [4]. The activity of R-1MAP was essentially equivalent to that of AEA in inhibiting the growth of C6 glioma cells. However, when tested for the inhibitory effects of AEA binding to the isolated rat brain CB1 receptors, arachidonoyl ethanolamide phosphate (AEA-P) has shown about 5-fold less potent as an agonist with a Ki value of about 200 nM [5]. In normotensive Dutch Belted rabbits of either gender, the phosphate ester of R-methanandamide reduced intraocular pressure (IOP) [1].
References:
1. Juntunen J, Huuskonen J, Laine K, et al. Anandamide prodrugs: 1. Water-soluble phosphate esters of arachidonylethanolamide and R-methanandamide[J]. European journal of pharmaceutical sciences, 2003, 19(1): 37-43.
2. W. A. Devane, L. Hanus, A. Breuer, et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258, 1946-1949(1992).
3. C. C. Felder, E. M. Briley, J. Axelrod, et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proceedings of the National Academy of Sciences of the United States of America 90, 7656-7660 (1993).
4. C. J. Fowler, K. O. Jonsson, A. Andersson, et al. Inhibition of C6glioma cell proliferation by anandamide, 1-arachidonoylglycerol, and by a water soluble phosphate ester of anandamide: Variability in response and involement of arachidonic acid. Biochemical Pharmacology 66, 757-767 (2003).
5. T. Sheskin, L. Hanus, J. Slager, et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. Journal of Medicinal Chemistry 40, 659-667 (1997).
| Cas No. | 649569-33-5 | SDF | |
| Synonyms | R-1MAP,(R)-(+)-Arachidonyl-1'-Hydroxy-2'-Propylamide Phosphate | ||
| Chemical Name | N-(2-phosphate-1R-methylethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide | ||
| Canonical SMILES | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(N([H])[C@H](C)COP(O)(O)=O)=O | ||
| Formula | C23H40NO5P | M.Wt | 441.5 |
| Solubility | ≤15mg/ml in DMSO;15mg/ml in dimethyl formamide | 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. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
|
1 mg | 5 mg | 10 mg |
| 1 mM | 2.265 mL | 11.325 mL | 22.6501 mL |
| 5 mM | 0.453 mL | 2.265 mL | 4.53 mL |
| 10 mM | 0.2265 mL | 1.1325 mL | 2.265 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
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Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )
Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 15 reference(s) in Google Scholar.)
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