Anandamide identification

CP 55940 (79) and nabilone (80) are synthetic ligands for the cannabiaoid receptor. However, the identification of the eicosanoid, anandamide (81), as an endogenous cannabimimetic has provided an important tool to study cannabiaoid receptor function. 

Anandamide inhibited the specific binding of [ H]-HU-243 to synaptosomal membranes in a manner typical of competitive ligands, with an inhibition constant (K ) of 39.0 + 5.0 nM. In this system, the of tsP-THC, a psychoactive compound of cannabis, was 46.0 + 3-0 nM. These were exciting results — the psychoactive compound from a higher plant and a chemically completely different compound in the brain were found to bind to the same brain receptor at about the same level of activity. Soon after the identification of anandamide, this compound was tested for its pharmacological activity. Anandamide administered i.p. in mice, caused... 

Why is that Why is chocolate the most frequently mentioned food in surveys about cravings (Actually, this is mostly true for young women men crave pizza.) While some scientists have argued that the cause Is certain compounds, such as anandamide or caffeine, which do have the potential for pharmacological activity, the consensus is that chocolate is addictive because of its flavor. Not its taste, however. Flavor is more than just taste smell and texture also come into play. Flavor chemist Dr. Sara Kisch proved this very effectively at the chocolate symposium. She handed out jelly beans of various flavors and asked us to sample them while holding our noses. They were indistinguishable. But identification was no problem once our nostrils were liberated. It was a dramatic demonstration of the role smells play in flavor detection. When the nose is pinched, no air can flow from the mouth to the nasal passage, where our... 

Fig. 3. Identification of anandamide precursors. Representative MSn spectra of anandamide precursor, NAPE extracted from biological samples.

Highly sensitive targeted lipidomic approaches are rapidly leading to the identification of new analogs of anandamide (Tan et al., 2006). The two major families of lipids that share common chemical structure with anandamide are FAEs and fatty acid amides. Although many of these lipids show no activity at CB receptors, they are known to bind and activate other receptors, such as transient receptor potential vanilloid type-1 (TRPV-1) and the nuclear receptor peroxisome proliferator-activated (PPAR-a). 

Lehtonen, M., Reisner, K., Auriola, S., Wong, G., and Callaway, J. (2008). Mass-spectrometric identification of anandamide and 2-arachidonoylglycerol in nematodes. Chem. Biodwers. 5, 2431. 

The history of hashish dates back to at least 2000 BC and is associated with a considerable folk-lore. The word "assassin" derives from the Arabic for "hashish-eater" and the introduction of hashish to Europe by Marco Polo initiated investigations that have culminated in the identification of a specific neural receptor for the active constituent cannabinoids of marijuana and in the isolation of an endogenous ligand, anandamide, for this receptor (12). ... 

Desarnaud F, Cadas H, Piomelli D (1995) Anandamide amidohydrolase activity in rat brain microsomes. Identification and partial characterization. J Biol Chem 270 6030-6035 Deutsch DG, Chin SA (1993) Enzymatic synthesis and degradation of anandamide, a cannabi-... 

CoMFA models for endocannahinoids have been developed using rigid classical CBs as templates. However, the inherent flexibility of the arachidonic acyl chain of anandamide has been an obstacle to the identification of an unambiguous overlay needed for COMFA studies. 

Identification of Anandamide as an Endogenous Cannabinoid Receptor Ligand.179... 

From the discovery of anandamide in the central nervous system and the identification of classical cannabinoid CB, and CBj receptors, both centrally and peripherally, the cardiovascular actions have received interest. To date there have been a number of studies which point to endocannabinoids having vasodilator actions, whereas the in vivo effects are less clear. One key point to emerge is that endocannabinoids may act via a range of mechanisms, of which action at vanilloid receptors is now well established. 

Karava V, Fasia L, Siafaka-Kapadai A. (2001) Anandamide amidohydrolase activity, released in the medium by Tetrahymena priformis. Identification and partial characterization. FEES Letters 508 327-331. 

Kaczocha M, Glaser ST, Deutsch DG. Identification of intracellular carriers for the endocannabinoid anandamide. Proc Natl Acad Sci USA. 2009 106(15) 6375-6380. 

The chemical synthesis of anandamide confirmed this structural identification, and allowed Mechoulam, Devane and their colleagues to determine its pharmacological properties. In vitro and in vivo tests showed a great similarity of effects between anandamide and cannabinoid drugs. Anandamide reduced the electrogenic contraction of mouse vas deferens and, most importantly, closely mimicked the behavioral responses induced by... 

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