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From the body

SEAStearoylethanolamide

Saturated endogenous N-acylethanolamine with no affinity for CB1 or CB2, part of the endocannabinoidome.

Endogenous
Level of detail

C₂₀H₄₁NO₂

CAS 111-57-9

Family
Endocannabinoid or related mediatorEndocannabinoidome
Molar mass
327.60 g/mol

Updated on

In plain terms

Stearoylethanolamide is a small fatty molecule the human body makes itself from stearic acid. It is found in the brain, in amounts comparable to anandamide, and also in muscle and breast milk. It does not bind cannabis receptors and does not come from hemp.

Receptors and activity

Target network

PPARγModulatorno measured value
  • Binds or modulates

The lower the cited value, the closer the target sits to SEA: one ring per factor of 100. A target with no measured value stays on the edge.

Where these targets live

Where each target has been found in humans, according to the cited studies. The map shows the target, not an effect of SEA.

Brain, side view
Body, front view
Blood

PPARγPPARγ found in 6 regions of the body

  1. Adipose tissuedenseHighest levels in adipose tissue1
  2. GutdenseHighly expressed in the large intestine1
  3. LiverpresentIntermediate levels in the liver1
  4. HeartpresentExpressed at lower levels in the heart2
  5. Immune cellspresentPresent in monocyte-derived macrophages3
  6. Blood vesselspresentVascular smooth muscle cells4

Map sources

  1. Fajas L et al. The organization, promoter analysis, and expression of the human PPARgamma gene. J Biol Chem, 1997 (new tab)
  2. Vidal-Puig AJ et al. Peroxisome proliferator-activated receptor gene expression in human tissues. Effects of obesity, weight loss, and regulation by insulin and glucocorticoids. J Clin Invest, 1997 (new tab)
  3. Chinetti G et al. Activation of proliferator-activated receptors alpha and gamma induces apoptosis of human monocyte-derived macrophages. J Biol Chem, 1998 (new tab)
  4. Marx N et al. Peroxisome proliferator-activated receptor gamma activators inhibit gene expression and migration in human vascular smooth muscle cells. Circ Res, 1998 (new tab)

Cited values

  1. PPARγModulatorno measured value cited
Bar length follows the measured value (Ki, Kd, EC50 or IC50), on one scale shared by every entry, from 100 µM to 0.1 nM. A target with no cited value has no bar.

Pharmacology

Stearoylethanolamide (SEA) is a fully saturated N-acylethanolamine, the C18:0 analogue of anandamide, present in the brain at comparable levels. It does not bind CB1 and CB2 receptors and does not activate the TRPV1 channel; Alharthi et al. (2018) conclude that it is neither an endocannabinoid nor an endovanilloid, which places it in the endocannabinoidome. In mice, Maccarrone et al. (2002) nevertheless observed effects similar to those of anandamide on catalepsy, motility, analgesia and body temperature, attributed to its own binding sites distinct from cannabinoid receptors; it also potentiated the anandamide-induced fall in cyclic AMP, hence the hypothesis of an « entourage » effect. In mice it reduced food intake by the intraperitoneal and oral routes (25 mg/kg), with a fall in liver SCD-1 mRNA (Terrazzino 2004). In vitro, it inhibited the aggregation of human platelets (Hudz 2022) and the nuclear translocation of NF-κB in rat macrophages (Kosiakova 2022). In humans it has only been measured as a marker, in the trapezius muscle of women with chronic neck and shoulder pain and in breast milk. No clinical trial has evaluated it.

Key sources.

History

Source
An endogenous mammalian compound, not reported in cannabis. Stearoylethanolamide is present in human, rat and mouse brain in amounts comparable to anandamide (Maccarrone 2002). In humans it has been measured in trapezius muscle microdialysate (Ghafouri 2011) and in breast milk (Bruun 2018). It derives from stearic acid, a saturated C18 fatty acid.

Biosynthetic pathway

In vivo

Like other N-acylethanolamines, it is formed from membrane phospholipids: an N-acyltransferase transfers a stearoyl residue onto phosphatidylethanolamine, and the resulting N-stearoyl-phosphatidylethanolamine is hydrolysed by a phospholipase D (NAPE-PLD) that releases stearoylethanolamide.

Classification

Family, origin and source verification

Family

Endocannabinoid or related mediator › Endocannabinoidome

Verification

Every fact on this entry was checked against its primary sources on 20 October 2026.

Wikipedia (English)

Stearoylethanolamide (new tab)

Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.

References

  1. Maccarrone M. et al., Cannabimimetic activity, binding, and degradation of stearoylethanolamide within the mouse central nervous system, Mol Cell Neurosci 2002 (new tab)PMID 12359156
  2. Maccarrone M. et al., Binding, degradation and apoptotic activity of stearoylethanolamide in rat C6 glioma cells, Biochem J 2002 (new tab)PMID 12010121
  3. Terrazzino S. et al., Stearoylethanolamide exerts anorexic effects in mice via down-regulation of liver stearoyl-coenzyme A desaturase-1 mRNA expression, FASEB J 2004 (new tab)PMID 15289450
  4. Movahed P. et al., Endogenous unsaturated C18 N-acylethanolamines are vanilloid receptor (TRPV1) agonists, J Biol Chem 2005 (new tab)PMID 16081411
  5. Alharthi N. et al., n-3 polyunsaturated N-acylethanolamines are CB2 cannabinoid receptor-preferring endocannabinoids, Biochim Biophys Acta Mol Cell Biol Lipids 2018 (new tab)PMID 30591150
  6. Sun Y.X. et al., Involvement of N-acylethanolamine-hydrolyzing acid amidase in the degradation of anandamide and other N-acylethanolamines in macrophages, Biochim Biophys Acta 2005 (new tab)PMID 16154384
  7. Kosiakova H. et al., The involvement of peroxisome proliferator-activated receptor gamma (PPARγ) in anti-inflammatory activity of N-stearoylethanolamine, Heliyon 2022 (new tab)PMID 36387464
  8. Hudz I.A. et al., N-Stearoylethanolamine Inhibits Integrin-Mediated Activation, Aggregation, and Adhesion of Human Platelets, J Pharmacol Exp Ther 2022 (new tab)PMID 35963618
  9. Ghafouri N. et al., High levels of N-palmitoylethanolamide and N-stearoylethanolamide in microdialysate samples from myalgic trapezius muscle in women, PLoS One 2011 (new tab)PMID 22125609
  10. Bruun S. et al., Satiety Factors Oleoylethanolamide, Stearoylethanolamide, and Palmitoylethanolamide in Mother's Milk Are Strongly Associated with Infant Weight at Four Months of Age, Nutrients 2018 (new tab)PMID 30428553
  11. Bachur N.R., Masek K., Melmon K.L., Udenfriend S., Fatty Acid Amides of Ethanolamine in Mammalian Tissues, J Biol Chem 1965 (new tab)PMID 14284696
  12. PubChem CID 27902, N-Stearoylethanolamine (new tab)

Identifiers

Names

Common name
Stearoylethanolamide
IUPAC name
N-(2-hydroxyethyl)octadecanamide
Other names
N-stearoylethanolamine · SEA · NSE · 18:0 NAE

Identifiers

Formula
C₂₀H₄₁NO₂
CAS
111-57-9
PubChem CID
27902(new tab)
ChEBI
CHEBI:85299(new tab)
InChIKey
OTGQIQQTPXJQRG-UHFFFAOYSA-N
SMILES
CCCCCCCCCCCCCCCCCC(=O)NCCO

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.