R-1 Methanandamide Phosphate

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Cat No: 10004281

Biochemicals - Lipids

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.{1134,2713} Since that time, a number of related endocannabinoids have been is...

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Territorial Availability: Available through Bertin Technologies only in France

Synonyms:

N-(2-phosphate-1R-methylethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide

Correlated keywords:

endocannabinoids neurotransmitters ligands AEA lipids CB1 CB2 receptors anandamides analogs agonists phosphates LPA lysophatidic acids neurochemistry neuroscience R1 cannabinoids cbs synthetic

Product Overview:
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.{1134,2713} Since that time, a number of related endocannabinoids have been isolated, most notably 2-arachidonoyl glycerol (2-AG).{2713} The phosphate ester of R-1 methanandamide, R-1MAP, has been tested as a water soluble prodrug analog of AEA.{11520} 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.{9580} 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.

Size	1 mg
Shipping	dry ice
CAS Number	649569-33-5
Molecular Formula	C₂₃H₄₀NO₅P
SMILES	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(N([H])[C@H](C)COP(O)(O)=O)=O
Molecular Weight	441,5
Formulation	A solution in ethanol
Purity	≥98%
Custom Code	2916.19
UNSPSC code	12352100

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Cayman Chemical's mission is to help make research possible by supplying scientists worldwide with the basic research tools necessary for advancing human and animal health. Our utmost commitment to healthcare researchers is to offer the highest quality products with an affordable pricing policy.

Our scientists are experts in the synthesis, purification, and characterization of biochemicals ranging from small drug-like heterocycles to complex biolipids, fatty acids, and many others. We are also highly skilled in all aspects of assay and antibody development, protein expression, crystallization, and structure determination.

Over the past thirty years, Cayman developed a deep knowledge base in lipid biochemistry, including research involving the arachidonic acid cascade, inositol phosphates, and cannabinoids. This knowledge enabled the production of reagents of exceptional quality for cancer, oxidative injury, epigenetics, neuroscience, inflammation, metabolism, and many additional lines of research.

Our organic and analytical chemists specialize in the rapid development of manufacturing processes and analytical methods to carry out clinical and commercial GMP-API production. Pre-clinical drug discovery efforts are currently underway in the areas of bone restoration and repair, muscular dystrophy, oncology, and inflammation. A separate group of Ph.D.-level scientists are dedicated to offering Hit-to-Lead Discovery and Profiling Services for epigenetic targets. Our knowledgeable chemists can be contracted to perform complete sample analysis for analytes measured by the majority of our assays. We also offer a wide range of analytical services using LC-MS/MS, HPLC, GC, and many other techniques.

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ISO Guide 34:2009

Cayman is a leader in the field of emerging drugs of abuse, providing high-purity Schedule I-V Controlled Substances to federally-licensed laboratories and qualified academic research institutions for forensic analyses. We are certified by ACLASS Accreditation Services with dual accreditation to ISO/IEC 17025:2005 and ISO Guide 34:2009.