Stearoylethanolamide - Misplaced Pages

Chemical compound

Stearoylethanolamide
Names

IUPAC name N-(2-Hydroxyethyl)octadecanamide
Identifiers
CAS Number	111-57-9
3D model (JSmol)	Interactive image
ChemSpider	25958
ECHA InfoCard	100.003.531
IUPHAR/BPS	3621
PubChem CID	27902
UNII	03XV449Q24
CompTox Dashboard (EPA)	DTXSID9042178
InChI InChI=1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h22H,2-19H2,1H3,(H,21,23)Key: OTGQIQQTPXJQRG-UHFFFAOYSA-N
SMILES CCCCCCCCCCCCCCCCCC(=O)NCCO
Properties
Chemical formula	C₂₀H₄₁NO₂
Molar mass	327.553 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Stearoylethanolamide (SEA) is an endocannabinoid neurotransmitter.

Stearoylethanolamide (C₂₀H₄₁NO₂; 18:0), also called N-(octadecanoyl)ethanolamine, is an N-acylethanolamine and the ethanolamide of octadecanoic acid (C₁₈H₃₆O₂; 18:0) and ethanolamine (MEA: C₂H₇NO), and functionally related to an octadecanoic acid.

Levels of SEA correlate with changes in pain intensity, indicating this SEA change, reflect the pain reduction effects of IPRP.

References

Mauro Maccarrone, Riccardo Pauselli, Marianna Di Rienzo, Alessandro Finazzi-Agrò (2002). "Binding, degradation and apoptotic activity of stearoylethanolamide in rat C6 glioma cells". Biochem J. 366 (Pt 1): 137–144. doi:10.1042/BJ20020438. PMC 1222758. PMID 12010121.{{cite journal}}: CS1 maint: multiple names: authors list (link)
PubChem. "N-(2-Hydroxyethyl)octadecanamide". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-09-27.
Stensson, Niclas; Gerdle, Björn; Rönne-Petersén, Linn; Yang, Liu L.; Lavebratt, Catharina; Falkenberg, Torkel; Ghafouri, Bijar (2022-02-26). "Investigating the Long-Term Effect of an Interdisciplinary Multimodal Rehabilitation Program on Levels of Bioactive Lipids and Telomerase Activity in Blood from Patients with Chronic Pain". Journal of Clinical Medicine. 11 (5): 1291. doi:10.3390/jcm11051291. ISSN 2077-0383. PMC 8911430. PMID 35268382.

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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