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From the body

PGE2-EAProstamide E2

A COX-2 metabolite of anandamide, with no established cannabinoid activity.

Endogenous
Level of detail

C₂₂H₃₇NO₅

CID 35021785

Family
Endocannabinoid or related mediatorEndocannabinoidome
Molar mass
395.50 g/mol

Updated on

In plain terms

Prostamide E2 is not a hemp molecule: it is a compound the body makes itself from anandamide, one of its internal cannabinoids, when an inflammation-linked enzyme, COX-2, comes into play. It does not behave like a cannabinoid and produces no high. Research is interested in it to understand inflammation and pain, but human data are lacking.

Receptors and activity

Target network

  • Activates

The lower the cited value, the closer the target sits to PGE2-EA: one ring per factor of 100. A target with no measured value stays on the edge.

Cited values

  1. Prostanoid EP3 receptorAgonistKi = 200 nM · human45 out of 100

    Ross et al. 2002, J Pharmacol Exp Ther (new tab) · binding on membranes of HEK cells transfected with human EP3; pKi 6.70 ± 0.13 versus 9.34 ± 0.06 for PGE2

  2. Prostanoid EP2 receptorAgonistKi = 468 nM · human39 out of 100

    Ross et al. 2002, J Pharmacol Exp Ther (new tab) · binding on membranes of HEK cells transfected with human EP2; pKi 6.33 ± 0.01 versus 9.03 ± 0.04 for PGE2

  3. Prostanoid EP4 receptorAgonistKi = 513 nM · human38 out of 100

    Ross et al. 2002, J Pharmacol Exp Ther (new tab) · binding on membranes of HEK cells transfected with human EP4; pKi 6.29 ± 0.06 versus 9.10 ± 0.04 for PGE2

  4. Prostanoid EP1 receptorAgonistKi = 2.5 µM · human27 out of 100

    Ross et al. 2002, J Pharmacol Exp Ther (new tab) · binding on membranes of HEK cells transfected with human EP1; pKi 5.61 ± 0.1 versus 8.31 ± 0.16 for PGE2

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

Prostamide E2 is the main oxygenation product of anandamide by cyclooxygenase-2, a reaction cyclooxygenase-1 does not catalyse, described in 1997 (Yu 1997). Its pharmacology is its own: one binding study finds weak affinities at EP1–EP4, two to three orders of magnitude below those of PGE2, with functional effects of the same order in isolated tissues (Ross 2002), while a later study detects no meaningful interaction with human recombinant prostanoid receptors, no inhibition of FAAH or of anandamide uptake and no TRPV1 activation, but a potent contraction of the cat iris, hence the hypothesis of dedicated « prostamide » receptors, still uncloned (Matias 2004). It is barely reconverted to PGE2: less than 3 % of prostamides are hydrolysed after four hours' incubation with rat brain, lung or liver homogenates (Matias 2004), and its plasma elimination is slower than that of the corresponding prostaglandin (Ritter 2012). The reported effects remain animal or cellular: in the renal medulla, prostamide E2 is the major COX-2 product and its intravenous administration in the rat lowered mean arterial pressure, increased renal blood flow and countered the effects of angiotensin II (Ritter 2012); the inhibition of IL-12p40 production by anandamide was attributed in part to this metabolite (Correa 2008). Physiological relevance in humans is not established and human data are lacking.

Key sources.

History

Source
An endogenous metabolite, absent from hemp: prostamide E2 occurs in no cannabis variety and is not a phytocannabinoid. It forms in animal tissues from anandamide wherever cyclooxygenase-2 is present or induced: the renal medulla, where COX-2 is enriched relative to the cortex and prostamide E2 is the major product of medullary microsomes (Ritter 2012), and the rabbit cornea, where prostamides appear after anandamide is supplied (Urquhart 2015). In FAAH-deficient mice, tissue concentrations of prostamide E2 after anandamide administration are far higher than in control mice, the competing hydrolysis pathway being absent (Weber 2004). Baseline endogenous concentrations remain very low.

Biosynthetic pathway

In vivo

Anandamide is oxygenated by cyclooxygenase-2, a reaction cyclooxygenase-1 does not catalyse, giving a PGH2 ethanolamide intermediate, and a prostaglandin E synthase then yields prostamide E2 (Yu 1997). The pathway therefore operates only in tissues expressing COX-2 and competes with anandamide hydrolysis by FAAH: in FAAH-deficient mice prostamide formation is markedly increased (Weber 2004), and COX-2 inhibition by celecoxib blocks the renal effects of anandamide attributed to a prostamide intermediate (Ritter 2012).

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. Yu, Ives & Ramesha 1997, J Biol Chem: synthesis of PGE2 ethanolamide from anandamide by COX-2 (new tab)PMID 9261124
  2. Ross et al. 2002, J Pharmacol Exp Ther: pharmacological characterisation of PGE2 ethanolamide (pKi EP1-EP4) (new tab)PMID 12023517
  3. Matias et al. 2004, J Pharmacol Exp Ther: in vitro pharmacology and metabolism of prostamides (new tab)PMID 14757851
  4. Ritter et al. 2012, J Pharmacol Exp Ther: production and actions of prostamide E2 in the renal medulla (new tab)PMID 22685343
  5. Correa et al. 2008, Biochem J: anandamide inhibits IL-12p40 production, possible involvement of prostamide E2 (new tab)PMID 17961121
  6. Ligresti et al. 2014, Br J Pharmacol: prostamide F2α receptor antagonism and FAAH inhibition (new tab)PMID 24102214
  7. Urquhart et al. 2015, J Lipid Res: prostamides and fatty acid ethanolamides in the rabbit cornea (new tab)PMID 26031663
  8. Weber et al. 2004, J Lipid Res: prostamide formation in the FAAH-deprived mouse (new tab)PMID 14729864
  9. PubChem CID 35021785, PGE2 ethanolamide (new tab)

Identifiers

Names

Common name
Prostamide E2
IUPAC name
(Z)-N-(2-hydroxyethyl)-7-[(1R,2R,3S)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enamide
Other names
PGE2-EA · prostaglandin E2 ethanolamide · PGE2 1-ethanolamide

Identifiers

Formula
C₂₂H₃₇NO₅
PubChem CID
35021785(new tab)
InChIKey
GKKWUSPPIQURFM-XXHBNTRVSA-N
SMILES
CCCCC[C@@H](/C=C/[C@H]1[C@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)NCCO)O)O

Machine-readable entry (JSON)

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