Docosatetraenoylethanolamide

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Docosatetraenoylethanolamide
Docosatetraenoyl ethanolamide.png
Names
Preferred IUPAC name
(7Z,10Z,13Z,16Z)-N-(2-Hydroxyethyl)docosa-7,10,13,16-tetraenamide
Other names
DEA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C24H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h6-7,9-10,12-13,15-16,26H,2-5,8,11,14,17-23H2,1H3,(H,25,27)/b7-6-,10-9-,13-12-,16-15- checkY
    Key: FMVHVRYFQIXOAF-DOFZRALJSA-N checkY
  • CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)NCCO
Properties
C24H41NO2
Molar mass 375.59 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Docosatetraenoylethanolamide (DEA) (Adrenoyl-ethanolamide) (Adrenoyl-EA)is an endogenous ethanolamide that has been shown to act on the cannabinoid (CB1) receptor.[1] DEA is similar in structure to anandamide (AEA, a recognized endogenous ligand for the CB1 receptor), containing docosatetraenoic acid in place of arachidonic acid. While DEA has been shown to bind to the CB1 receptor with similar potency and efficacy as AEA, its role as a cannabinergic neurotransmitter is not well understood.

Docosatetraenoylethanolamide (DEA) has been found in Tropaeolum tuberosum (Mashua) and Leonotis leonurus (Wild Dagga / Lion's Tail) [2]

References[edit]

  1. ^ Hanus, L.; Gopher, A.; Almog, S.; et al. (1993). "Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor". J Med Chem. 36 (20): 3032–3034. doi:10.1021/jm00072a026. PMID 8411021.
  2. ^ Hunter, E.; Stander, M.; Kossmann, J.; Chakraborty, S.; Prince, S.; Peters, S.; Loedolff, Bianke (2020). "Toward the identification of a phytocannabinoid-like compound in the flowers of a South African medicinal plant (Leonotis leonurus)". BMC Research Notes. 13 (1): 522. doi:10.1186/s13104-020-05372-z. PMC 7653773. PMID 33172494.