View source for Virodhamine

{{chembox
| ImageFile = virodhamine.png
| IUPACName = 2-aminoethyl (5Z,8Z,11Z,14Z)-icosa- 5,8,11,14-tetraenoate
| OtherNames= ''O''-Arachidonoyl ethanolamine
| Section1 = {{Chembox Identifiers
| CASNo = 443129-35-9 
| PubChem = 5712057
| SMILES = CCCCC\C=C/C\C= C/C\C=C/C\C=C/CCCC(=O)OCCN
  }}
{{Chembox Properties
| Formula =  C<sub>22</sub>H<sub>37</sub>NO<sub>2</sub>
| MolarMass = 347.53468
  }}
}}

'''Virodhamine''' ('''''O''-arachidonoyl ethanolamine''') is an [[Cannabinoids|endocannabinoid]] and a nonclassic [[eicosanoid]], derived from [[arachidonic acid]]. ''O''-Arachidonoyl ethanolamine is [[arachidonic acid]] and [[ethanolamine]] joined by an [[ester]] linkage, the opposite of the [[amide]] linkage found in [[anandamide]]. Based on this opposite orientation, the molecule was named virodhamine from the Sanskrit word ''virodha'', which means opposition. It acts as an [[Receptor antagonist|antagonist]] of the [[Cannabinoid receptor|CB<sub>1</sub> receptor]] and [[agonist]] of the [[Cannabinoid_receptor#CB2|CB<sub>2</sub> receptor]]. Concentrations of virodhamine  in the human hippocampus are similar to those of [[anandamide]], but they are 2- to 9-fold higher in peripheral tissues that express CB<sub>2</sub>. Virodhamine lowers body temperature in mice, demonstrating cannabinoid activity ''in vivo''.<ref name="pmid12023533">{{cite journal
|author=Porter AC, Sauer JM, Knierman MD, ''et al.''
|title=Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor
|journal=J. Pharmacol. Exp. Ther.
|volume=301
|issue=3
|url=http://jpet.aspetjournals.org/cgi/reprint/301/3/1020
|pages=1020–4
|year=2002
|pmid=12023533
|doi=10.1124/jpet.301.3.1020
|accessdate=2007-10-31
}}</ref>

== See also ==
* [[Anandamide]]
* [[Oleamide]]

==References==
{{Reflist|2}}


{{Cannabinoids}}
{{Eicosanoids}}
{{Neurotransmitters}}

[[Category:Eicosanoids]]
[[Category:Cannabinoids]]


{{biochem-stub}}

[[it:Virodamina]]
[[Category:2Fix]]