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
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL321585
ChemSpider	4445444
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-Key: FMVHVRYFQIXOAF-DOFZRALJSA-N
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 , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Docosatetraenoylethanolamide (DEA) (Adrenoyl-ethanolamide) (Adrenoyl-EA) is an endogenous ethanolamide that has been shown to act on the cannabinoid (CB₁) receptor. 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).

References

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.
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.

Neurotransmitters

Amino acid-derived

Major excitatory /
inhibitory systems

Glutamate system	Agmatine Aspartic acid (aspartate) Glutamic acid (glutamate) Glutathione Glycine GSNO GSSG Kynurenic acid NAA NAAG Proline Serine
GABA system	GABA GABOB GHB
Glycine system	α-Alanine β-Alanine Glycine Hypotaurine Proline Sarcosine Serine Taurine
GHB system	GHB T-HCA (GHC)

Biogenic amines

Monoamines	6-OHM Dopamine Epinephrine (adrenaline) NAS (normelatonin) Norepinephrine (noradrenaline) Serotonin (5-HT)
Trace amines	3-Iodothyronamine N-Methylphenethylamine N-Methyltryptamine m-Octopamine p-Octopamine Phenylethanolamine Phenethylamine Synephrine Tryptamine m-Tyramine p-Tyramine
Others	Histamine

Neuropeptides

See here instead.

Lipid-derived

Endocannabinoids

Neurosteroids

See here instead.

Nucleobase-derived

Nucleosides

Adenosine system	ADP AMP ATP

Vitamin-derived

Miscellaneous

Cholinergic system	Acetylcholine

Gasotransmitters	Carbon monoxide (CO) Hydrogen sulfide (H₂S) Nitric oxide (NO)

Candidates	Acetaldehyde Ammonia (NH₃) Carbonyl sulfide (COS) Nitrous oxide (N₂O) Sulfur dioxide (SO₂)

Cannabinoid receptor modulators

Receptor
(ligands)

CB₁Tooltip Cannabinoid receptor type 1

Agonists (abridged, full list)	2-AG 2-AGE (noladin ether) 11-Hydroxy-THC α-Amyrin · β-Amyrin AB-CHMINACA AM-1172 AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 Anandamide Arvanil AZ-11713908 Cannabinol CB-13 CP 47,497 CP 55,940 Dimethylheptylpyran DEA ECG EGCG Epicatechin Gallocatechol (gallocatechin) Honokiol HU-210 JWH-007 JWH-015 JWH-018 JWH-073 Kavain L-759,633 Levonantradol Menabitan Nabilone Nabitan NADA O-1812 Oleamide Pravadoline Serinolamide A THC (dronabinol) UR-144 WIN 55,212-2 Yangonin
Inverse agonists	AM-251 INV-202 Monlunabant Rimonabant Surinabant Taranabant TM-38837 Zevaquenabant
Antagonists	AM-6545 Cannabidiol Cannabigerol Drinabant Falcarinol (carotatoxin) Hemopressin Ibipinabant LY-320,135 MK-9470 NESS-0327 O-2050 Otenabant PF-514273 PipISB Rosonabant Selonabant THCV VCHSR Virodhamine

CB₂Tooltip Cannabinoid receptor type 2

Agonists

Antagonists

NAGly
(GPR18)

Agonists	Abnormal cannabidiol ACPA AM251 Anandamide Cannabidiol NADGly THC (dronabinol) O-1602
Antagonists	PSB-CB5 O-1918

GPR55

Agonists	2-AGE (noladin ether) 2-ALPI Abnormal cannabidiol AM-251 CID1011163 CID1252842 CID1792579 CP 55,940 GSK-494581A Lysophosphatidylinositol ML-184 ML-185 ML-186 O-1602 Oleoylethanolamide Palmitoylethanolamide THC (dronabinol)
Antagonists	Cannabidiol CID-16020046 ML-191 ML-192 ML-193 O-1918 PSB-SB-487 PSB-SB-1202 PSB-SB-1203 Tetrahydromagnolol

GPR119

Agonists	2-Oleoylglycerol Anandamide APD668 AR-231,453 AS-1269574 MBX-2982 N-Oleoyldopamine Oleoylethanolamide Olvanil PSN-375,963 PSN-632,408

Transporter
(modulators)

eCBTsTooltip Endocannabinoid transporter	Inhibitors: 5'-DMH-CBD AM-404 AM-1172 Arachidonoyl serotonin Arvanil Cannabidiol Guineensine LY-2183240 O-2093 OMDM-2 Paracetamol (acetaminophen) SB-FI-26 UCM-707 URB-597 VDM-11 WOBE490 WOBE491 WOBE492

Enzyme
(modulators)

FAAHTooltip Fatty acid amide hydrolase	Inhibitors: 4-Nonylphenylboronic acid AACOCF₃ AM-404 Arachidonoyl serotonin BIA 10-2474 Biochanin A Genistein IDFP JNJ-1661010 JNJ-42165279 JZL-195 Kaempferol LY-2183240 MAFP Palmitoylisopropylamide Paracetamol (acetaminophen) PF-3845 PF-750 Redafamdastat (JZP-150, PF-04457845) SA-47 SA-57 TAK 21d TC-F 2 UCM710 URB-597 Activators: PDP-EA
MAGL	Inhibitors: ABX-1431 IDFP JJKK 048 JW 642 JZL-184 JZL-195 JZP-361 KML 29 MAFP MJN110 NAM Pristimerin URB-602
ABHD6	Inhibitors: JZP-169 JZP-430 KT182 KT185 KT195 KT203 LEI-106 ML294 ML295 ML296 UCM710 WWL-70
ABHD12	Inhibitors: Betulinic acid Maslinic acid MAFP Oleanolic acid Orlistat (tetrahydrolipstatin) Ursolic acid

Others

Precursors: Phosphatidylethanolamine
NAPE
Diacylglycerol

Others: 2-PG (directly potentiates activity of 2-AG at CB₁ receptor)
ARN-272 (FAAH-like anandamide transporter inhibitor)

See also: Receptor/signaling modulators; Cannabinoids (cannabinoids by structure)

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