Docosatetraenoylethanolamide

Docosatetraenoylethanolamide

Names
Preferred IUPAC name (7Z,10Z,13Z,16Z)-N-(2-Hydroxyethyl)docosa-7,10,13,16-tetraenamide
Other names DEA
Identifiers
CAS Number	150314-35-5^N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL321585^Y
ChemSpider	4445444^Y
IUPHAR/BPS	5445
PubChem CID	5282273
CompTox Dashboard (EPA)	DTXSID501028460
InChI 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-^Y Key: FMVHVRYFQIXOAF-DOFZRALJSA-N^Y
SMILES CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)NCCO
Properties
Chemical formula	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). N verify (what is ^YN ?) Infobox references

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

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.