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From the body

OEAOleoylethanolamide

An endogenous N-acylethanolamine linked to satiety in animals, a PPAR-α ligand that does not bind cannabinoid receptors.

Endogenous
Level of detail

C₂₀H₃₉NO₂

CAS 111-58-0

Family
Endocannabinoid or related mediatorEndocannabinoidome
Molar mass
325.50 g/mol

Updated on

In plain terms

OEA is a lipid from the same family as anandamide, made notably by the gut after a fatty meal. It does not bind the cannabinoid receptors. In animals, it has been linked to the feeling of fullness.

Receptors and activity

Target network

TRPV1ModulatorEC50 = 2 µM · not specifiedTRPV1 currents in Xenopus oocytes, only after PKC stimulation
  • Activates
  • Binds or modulates

The lower the cited value, the closer the target sits to OEA: 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 OEA.

Brain, side view
Body, front view
Blood

TRPV1TRPV1 found in 7 regions of the body

  1. Sensory gangliapresentExpressed in dorsal root ganglia1
  2. Spinal cordpresentNerve fibres in the spinal dorsal horn2
  3. CortexpresentParietal cortex neurons (layers 3 and 5)3
  4. SkinpresentWidely distributed in the skin4
  5. Blood vesselspresentPresent on dermal blood vessels4
  6. BonepresentPresent on osteoclasts5
  7. LiverpresentRNA enriched in the liver6

Map sources

  1. Cortright DN et al. The tissue distribution and functional characterization of human VR1. Biochem Biophys Res Commun, 2001 (new tab)
  2. Facer P et al. Differential expression of the capsaicin receptor TRPV1 and related novel receptors TRPV3, TRPV4 and TRPM8 in normal human tissues and changes in traumatic and diabetic neuropathy. BMC Neurol, 2007 (new tab)
  3. Mezey E et al. Distribution of mRNA for vanilloid receptor subtype 1 (VR1), and VR1-like immunoreactivity, in the central nervous system of the rat and human. Proc Natl Acad Sci U S A, 2000 (new tab)
  4. Ständer S et al. Expression of vanilloid receptor subtype 1 in cutaneous sensory nerve fibers, mast cells, and epithelial cells of appendage structures. Exp Dermatol, 2004 (new tab)
  5. Rossi F et al. The endovanilloid/endocannabinoid system in human osteoclasts: possible involvement in bone formation and resorption. Bone, 2009 (new tab)
  6. Human Protein Atlas. TRPV1 tissue expression (RNA consensus) (new tab)

Cited values

  1. PPAR-αAgonistno measured value cited
  2. GPR119Agonistno measured value cited
  3. TRPV1ModulatorEC50 = 2 µM · not specified28 out of 100

    Ahern 2003, J Biol Chem 278:30429 (TRPV1, PKC-dependent) (new tab) · TRPV1 currents in Xenopus oocytes, only after PKC stimulation

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

Oleoylethanolamide (OEA, NAE 18:1) is the monounsaturated analogue of anandamide. In 2001, Daniele Piomelli's team showed in rats that fasting reduces its biosynthesis in the small intestine and that its anorexic effect disappears after peripheral sensory fibres are destroyed with capsaicin, with no effect when injected into the brain ventricles (Rodríguez de Fonseca et al. 2001). Despite its kinship with anandamide, it does not bind cannabinoid receptors; it binds PPAR-α with high affinity, and its effects on intestinal gene expression disappear in mice lacking PPAR-α (Fu et al. 2003). In rats, a duodenal infusion of fat, but not of protein or carbohydrate, increases its intestinal mobilisation, which depends on the CD36 transporter; knocking out CD36 or PPAR-α abolishes fat-induced satiety in mice (Schwartz et al. 2008). It has also been proposed as an endogenous ligand of GPR119 (Overton et al. 2006), and activates TRPV1 only after the channel is phosphorylated by PKC (EC50 ≈ 2 µM; Ahern 2003). FAAH controls its breakdown: in FAAH−/− mice, its brain content is about 40 times higher (Cravatt et al. 2001).

Key sources.

History

Source
Endogenous (endocannabinoidome mediator), mobilised notably in the proximal small intestine after fat intake

Biosynthetic pathway

In vivo

Formed from an N-acyl-phosphatidylethanolamine (N-oleoyl-PE) cleaved by NAPE-PLD (Okamoto et al. 2004). In rats, its mobilisation in the proximal small intestine rises after duodenal infusion of fat, not of protein or carbohydrate, and uses dietary oleic acid taken up by the CD36 transporter (Schwartz et al. 2008).

Classification

Family, origin and source verification

Family

Endocannabinoid or related mediator › Endocannabinoidome

Chemistry

Mono-unsaturated N-acylethanolamine (NAE 18:1)

Verification

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

Wikipedia (English)

Oleoylethanolamide (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. Rodríguez de Fonseca et al. 2001, Nature 414:209 (anorexigenic mediator regulated by feeding) (new tab)PMID 11700558
  2. Fu et al. 2003, Nature 425:90 (PPAR-α; no binding to cannabinoid receptors) (new tab)PMID 12955147
  3. Schwartz et al. 2008, Cell Metab 8:281 (dietary fat, CD36, satiety) (new tab)PMID 18840358
  4. Overton et al. 2006, Cell Metab 3:167 (GPR119) (new tab)PMID 16517404
  5. Ahern 2003, J Biol Chem 278:30429 (TRPV1, PKC-dependent) (new tab)PMID 12761211
  6. Cravatt et al. 2001, PNAS 98:9371 (FAAH−/− mice) (new tab)PMID 11470906

Identifiers

Names

Common name
Oleoylethanolamide
IUPAC name
(Z)-N-(2-hydroxyethyl)octadec-9-enamide
Other names
N-oleoylethanolamine · 18:1 NAE

Identifiers

Formula
C₂₀H₃₉NO₂
CAS
111-58-0
PubChem CID
5283454(new tab)
ChEBI
CHEBI:71466(new tab)
InChIKey
BOWVQLFMWHZBEF-KTKRTIGZSA-N
SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)NCCO

Machine-readable entry (JSON)

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