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From the body

POEAPalmitoleoylethanolamide

An endogenous 16:1 N-acylethanolamine, an agonist of the lipid sensor GPR119, with no cannabinoid activity.

Endogenous
Level of detail

C₁₈H₃₅NO₂

CAS 94421-67-7

Family
Endocannabinoid or related mediatorEndocannabinoidome
Molar mass
297.50 g/mol

Updated on

In plain terms

POEA is a small fatty molecule the body makes itself from a dietary fatty acid. Small amounts are found in human blood and in plant foods. The available work concerns metabolism and body weight in animals; in humans, only concentration measurements have been published.

Receptors and activity

Target network

  • Activates

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

Cited values

  1. GPR119Agonistno measured value cited

    One of the three most potent agonists identified among endocannabinoid-like lipids, with oleoylethanolamide and linoleoylethanolamide, of similar potencies; no EC50 is given in the study's abstract. Its intestinal levels do not rise after refeeding in the mouse, unlike those of LEA and 2-oleoylglycerol (Syed 2012)

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

Palmitoleoylethanolamide (POEA) is an endogenous N-acylethanolamine, close to palmitoylethanolamide (16:0) and oleoylethanolamide (18:1), formed by the NAPE route and then hydrolysed by FAAH. Its best-established target is not a cannabinoid receptor but the lipid sensor GPR119: in a screen of endocannabinoid-related lipids it ranks among the three most potent agonists, with OEA and LEA, at similar potency; the same authors note, however, that its intestinal levels do not change on refeeding, unlike those of LEA and 2-oleoylglycerol, which they take to be the physiologically relevant endogenous agonists (Syed 2012). Activity at PPAR-α remains a hypothesis based on the resemblance to OEA, with no direct demonstration (Tovar 2021), and no action at CB1 or CB2 has been reported. In Sprague-Dawley rats on a hypercaloric cafeteria diet, repeated administration decreased weight, liver steatosis, inflammation and dyslipidaemia, with a profile almost identical to that of OEA (Tovar 2021). Unlike palmitoylethanolamide and anandamide, POEA had little or no effect on formalin-evoked pain (Calignano 2001). Human data are limited to concentration measurements: in young alcohol binge drinkers, plasma POEA was elevated during abstinence and correlated with the expression of inflammatory markers in peripheral blood mononuclear cells (Anton 2018). No clinical administration study has been published and no therapeutic benefit can be asserted.

Key sources.

History

Source
An endogenous mammalian molecule, measured in particular in human plasma in N-acylethanolamine profiling (Anton 2018). N-acylethanolamines, including this one, are also more abundant in plant-based foods than in animal products (Vitaglione 2019). It is not produced by cannabis. Its precursor is palmitoleic acid (C16:1), supplied by the diet or formed in the body (Tovar 2021).

Biosynthetic pathway

In vivo

Formation follows the classical N-acylethanolamine route: an N-acyltransferase transfers palmitoleic acid onto a membrane phosphatidylethanolamine to give N-palmitoleoyl-phosphatidylethanolamine (NAPE), which a specific phospholipase D (NAPE-PLD) then cleaves to release POEA (Tsuboi 2018). Production therefore depends on the availability of palmitoleic acid, which links this mediator to dietary fat composition (Tovar 2021).

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)

No dedicated article.

References

  1. Syed et al. 2012, Am J Physiol Endocrinol Metab: regulation of GPR119 by endocannabinoid-like lipids (new tab)PMID 23074242
  2. Calignano, La Rana & Piomelli 2001, Eur J Pharmacol: antinociceptive activity of palmitoylethanolamide; palmitoleoylethanolamide has no notable effect on formalin (new tab)PMID 11426841
  3. Tovar et al. 2021, Nutrients: palmitoleoylethanolamide compared with oleoylethanolamide in diet-induced obesity in the rat (new tab)PMID 34444748
  4. Anton et al. 2018, Addict Biol: plasma elevation of oleoylethanolamide and palmitoleoylethanolamide in young binge drinkers (new tab)PMID 29178411
  5. Vitaglione et al. 2019, Food Chem: food database of NAPEs, NAEs and endocannabinoids and daily intakes (new tab)PMID 31351254
  6. Tsuboi et al. 2018, Inflamm Regen: metabolism of endocannabinoids and N-acylethanolamines (review) (new tab)PMID 30288203
  7. PubChem CID 9835868, palmitoleoyl ethanolamide (new tab)
  8. LIPID MAPS LMFA08040043, palmitoleoyl-EA (new tab)

Identifiers

Names

Common name
Palmitoleoylethanolamide
IUPAC name
(Z)-N-(2-hydroxyethyl)hexadec-9-enamide
Other names
N-palmitoleoylethanolamine · Palmitoleoyl-EA · 16:1 NAE

Identifiers

Formula
C₁₈H₃₅NO₂
CAS
94421-67-7
PubChem CID
9835868(new tab)
InChIKey
WFRLANWAASSSFV-FPLPWBNLSA-N
SMILES
CCCCCC/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.