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From the body

O-AEAVirodhamine

Ester isomer of anandamide, a CB1 partial agonist and full CB2 agonist, a putative endocannabinoid.

Endogenous
Level of detail

C₂₂H₃₇NO₂

CAS 287937-12-6

Family
Endocannabinoid or related mediatorPutative
Molar mass
347.50 g/mol

Updated on

In plain terms

Virodhamine is a molecule that the human body makes itself, and not a hemp compound. It closely resembles anandamide, a natural messenger of the endocannabinoid system, with which it shares exactly the same atoms, simply assembled differently. Researchers have been studying it since 2002, but its precise role in the body remains unknown.

Receptors and activity

Target network

CB1Partial agonistKi = 1.7 µM · human[3H]CP55,940, neocortical synaptosomes (912 nM with protease inhibitor)
  • Activates
  • Blocks or inhibits

The lower the cited value, the closer the target sits to O-AEA: 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 O-AEA.

Brain, side view
Body, front view
Blood

CB1CB1 found in 7 regions of the body

  1. Basal gangliadenseMost dense in basal ganglia outflow nuclei1
  2. CerebellumdenseVery dense in the cerebellum1
  3. HippocampusdenseVery high concentrations in the hippocampus2
  4. AmygdaladenseHigh concentrations in the amygdala2
  5. CortexpresentPresent throughout the neocortex2
  6. Adipose tissuepresentExpressed in adipose tissue3
  7. GutpresentColonic epithelium, smooth muscle and plexus4

Map sources

  1. Herkenham M et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A, 1990 (new tab)
  2. Glass M et al. Cannabinoid receptors in the human brain: a detailed anatomical and quantitative autoradiographic study in the fetal, neonatal and adult human brain. Neuroscience, 1997 (new tab)
  3. Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
  4. Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)

Cited values

  1. CB1Partial agonistKi = 1.7 µM · human29 out of 100

    Steffens M. et al., Biochem Pharmacol 2005 (new tab) · [3H]CP55,940, neocortical synaptosomes (912 nM with protease inhibitor)

  2. CB2Agonistno measured value cited
  3. GPR55Partial agonistno measured value cited
  4. Putative endothelial cannabinoid receptorAgonistno measured value cited
  5. MAO-BInhibitorIC50 = 710 nM · human36 out of 100

    Pandey P. et al., Biochem Pharmacol 2018 (new tab) · recombinant enzyme; Ki 258 nM, irreversible

  6. MAO-AInhibitorIC50 = 38.7 µM · human7 out of 100

    Pandey P. et al., Biochem Pharmacol 2018 (new tab) · recombinant enzyme

  7. CYP2J2Inhibitorno measured value cited
  8. FAAHInhibitorIC50 = 13.8 µM · human14 out of 100

    Steffens M. et al., Neurosci Lett 2005 (new tab) · anandamide hydrolysis, neocortex

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

A constitutional isomer of anandamide, virodhamine joins arachidonic acid and ethanolamine through an ester bond instead of an amide bond. Porter et al. (2002), who described it, characterise it as a CB1 partial agonist with in vivo antagonist activity and as a full CB2 agonist; in human neocortex its CB1 affinity is micromolar (Ki 1740 nM; Steffens 2005). IUPHAR (Pertwee 2010) lists it among molecules that may also serve as endocannabinoids, noting conflicting results: its status remains putative. It also modulates GPR55 as a partial agonist and relaxes the human pulmonary artery through the putative endothelial cannabinoid receptor. Outside the cannabinoid system, it inhibits monoamine oxidase B, the cardiac epoxygenase CYP2J2, FAAH and anandamide transport. Its levels exceed those of anandamide in peripheral tissues, notably porcine myocardium. The biosynthetic route is not identified, human data are lacking and its physiological function remains undetermined.

Key sources.

History

Source
An endogenous mammalian compound, not reported in cannabis. Porter et al. (2002) measured it in rat brain and human hippocampus at levels comparable to anandamide, and at concentrations 2 to 9 times higher in peripheral tissues that express the CB2 receptor. In porcine left ventricle, Carnevale et al. (2018) report a level 9.6 times higher than that of anandamide.

Biosynthetic pathway

In vivo

The route of formation is not elucidated. Structurally, virodhamine is the ester of arachidonic acid and ethanolamine, a constitutional isomer of anandamide, which joins the same two fragments through an amide bond.

Classification

Family, origin and source verification

Family

Endocannabinoid or related mediator › Putative

Verification

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

Wikipedia (English)

Virodhamine (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. Porter A.C. et al., Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor, J Pharmacol Exp Ther, 2002 (new tab)PMID 12023533
  2. Steffens M. et al., Binding affinity and agonist activity of putative endogenous cannabinoids at the human neocortical CB1 receptor, Biochem Pharmacol, 2005 (new tab)PMID 15588725
  3. Steffens M. et al., Fatty acid amidohydrolase in human neocortex: activity in epileptic and non-epileptic brain tissue and inhibition by putative endocannabinoids, Neurosci Lett, 2005 (new tab)PMID 15923084
  4. Sharir H. et al., The endocannabinoids anandamide and virodhamine modulate the activity of the candidate cannabinoid receptor GPR55, J Neuroimmune Pharmacol, 2012 (new tab)PMID 22454039
  5. Kozłowska H. et al., Virodhamine relaxes the human pulmonary artery through the endothelial cannabinoid receptor and indirectly through a COX product, Br J Pharmacol, 2008 (new tab)PMID 18806815
  6. Carnevale L.N. et al., Endocannabinoid virodhamine is an endogenous inhibitor of human cardiovascular CYP2J2 epoxygenase, Biochemistry, 2018 (new tab)PMID 30285425
  7. Pandey P. et al., Interactions of endocannabinoid virodhamine and related analogs with human monoamine oxidase-A and -B, Biochem Pharmacol, 2018 (new tab)PMID 29958841
  8. Brantl S.A. et al., Activation of platelets by the endocannabinoids 2-arachidonoylglycerol and virodhamine is mediated by their conversion to arachidonic acid and thromboxane A2, Platelets, 2014 (new tab)PMID 24102401
  9. Pertwee R.G. et al., International Union of Basic and Clinical Pharmacology. LXXIX. Cannabinoid receptors and their ligands: beyond CB1 and CB2, Pharmacological Reviews, 2010 (new tab)PMID 21079038
  10. PubChem CID 5712057, Virodhamine, National Library of Medicine (new tab)

Identifiers

Names

Common name
Virodhamine
IUPAC name
2-aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Other names
O-arachidonoylethanolamine · O-AEA

Identifiers

Formula
C₂₂H₃₇NO₂
CAS
287937-12-6
PubChem CID
5712057(new tab)
ChEBI
CHEBI:183424(new tab)
InChIKey
DLHLOYYQQGSXCC-DOFZRALJSA-N
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN

Machine-readable entry (JSON)

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