Anandamide
Chemical name	(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl) icosa-5,8,11,14-tetraenamide or arachidonoylethanolamide
Chemical formula	C22H37NO2
Molecular mass	347.53 g/mol
CAS number	94421-68-8
SMILES	CCCCCC=C/CC=C/CC=C /CC=C/CCCC(NCCO)=O

Anandamide, also known as arachidonoylethanolamine or AEA, is a naturally occurring endogenous cannabinoid neurotransmitter found in the brain of animals, as well as other organs. It was isolated, and its structure elucidated by William Devane and Lumír Hanuš in the Laboratory of Raphael Mechoulam, at the Hebrew University in Jerusalem in 1992. The name is taken from the Sanskrit word ananda, which means "bliss", and amide. IUPAC nomenclature is a systematic way of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... See also Avogadros number Atomic mass unit Dalton (unit) External links Learning by Simulations Calculation of Molecular Formulas from Molecular Masses Categories: Chemistry stubs | Mass | Chemical properties ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Chemical structure of Anandamide Selfmade by cacycle File links The following pages link to this file: Anandamide Categories: GFDL images ... Cannabinoids are a group of chemicals which activate the bodys cannabinoid receptors. ... Neurotransmitters are chemicals that are used to relay, amplify and modulate electrical signals between a neuron and another cell. ... Sanskrit ( संस्कृतम्) is a classical language of India and a liturgical language of Hinduism, Buddhism, and Jainism. ... Ananda(Ch:阿難) was one of many principal disciples of the Buddha, a devout attendant and was renowned as the Ananda was the first cousin of the Buddha, and was devotedly attached to him. ... In chemistry, the term amide has several meanings. ...

Anandamide's effects can be either central, in the brain, or peripheral, in other parts of the body. These distinct effects are mediated by the CB1 recepter in the nervous system, and the CB2 receptor in the periphery. The latter is mainly involved in functions of the immune system.

These receptors are part of the largest known family of receptors, the G protein-coupled receptors, which - in this case - has a distinctive pattern in which the receptor molecule spans the cell membrane seven times over. The CB1 receptor is one of the most numerous in the nervous system In cell biology, G-protein-coupled receptors, also known as GPCR, seven transmembrane receptors, heptahelical receptors, or 7TM receptors, are a class of transmembrane receptors. ...

Anandamide recepters were originally discovered as being sensitive to Δ⁹-tetrahydrocannabinol (Δ⁹-THC), which is among the psychoactive cannabinoids found in cannabis. The discovery of anandamide came from research into CB1 and CB2, as it was inevitable that a naturally occuring (endogenous) chemical would be found to effect these receptors. Tetrahydrocannabinol, also known as THC, Δ9-THC, Δ9-tetrahydrocannabinol (delta-9-tetrahydrocannabinol), Δ¹-tetrahydrocannabinol (using an older numbering scheme), or dronabinol, is the main psychoactive substance found in the Cannabis plant. ... Species Cannabis indica Cannabis ruderalis Cannabis sativa Cannabis is a genus of flowering plant that includes one or more species. ...

Endogenous cannabinoids occur in minute quantities in cocoa (fermented Theobroma cacao) beans, and in chocolate, though there is some controversy over whether they have any effects on the body in these quantities. In its strictest sense, fermentation (formerly called zymnosis) is the anaerobic metabolic breakdown of a nutrient molecule, such as glucose, without net oxidation. ... Binomial name Theobroma cacao L. Cacao (Theobroma cacao) is a small (4-8 m tall) evergreen tree in the family Sterculiaceae, native to tropical South America, but now cultivated throughout the tropics. ... Chocolate comes in dark, milk, and white varieties with cocoa solids contributing to the brown coloration. ...

Anandamide receptors have been shown to be involved in the management of short term memory. Studies are under way to explore what role anandamide plays in human behavior, such as eating and sleep patterns, and the part it plays in pain relief.

Anandamide is also important for implantation of the early stage embryo in its blastocyst form into the uterus. Therefore cannabinoids like Δ⁹-THC might interfere with the earliest stages of human pregnancy. Embryos (and one tadpole) of the wrinkled frog (Rana rugosa). ... Embryogenesis is the process of cell division and cellular differentiation which leads to the development of an embryo. ... Female internal reproductive anatomy The uterus or womb is the major female reproductive organ of most mammals, including humans. ...

Moreover, anandamide is thought to be an endogenous ligand for vanilloid receptors (which are involved in the transduction of acute and inflammatory pain signals), activating the receptor in a PKC-dependent (protein kinase C-dependent) manner.

See also

• Tetrahydrocannabinol (THC)

Tetrahydrocannabinol, also known as THC, Δ9-THC, Δ9-tetrahydrocannabinol (delta-9-tetrahydrocannabinol), Δ¹-tetrahydrocannabinol (using an older numbering scheme), or dronabinol, is the main psychoactive substance found in the Cannabis plant. ...

References

• Bir, Levent Sinan & Ercanb, Sevim (2005), "Effects of intrathecal anandamide on somatosensory evoked responses in rats", Experimental Neurology. PMID 16289169
• Nature Medicine 10, 19 - 20 (2004) THC: moderation during implantation